Title: Discover Top Chestertown Hotels for 2026 | Expedia.co.uk [Chestertown Travel Guide](https://expedia.co.uk/Chestertown.dx7215)[Holiday Rentals in Chestertown](https://expedia.co.uk/Chestertown-Holiday-Rentals.d7215.Travel-Guide-HolidayRentals)[Chestertown Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chestertown.d7215.Car-Hire-Guide)[Chestertown Holidays](https://expedia.co.uk/Chestertown.d7215.Holidays-City-Breaks) ![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Chestertown Pool [](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&amenities=POOL) Hot tub [](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&amenities=HOT_TUB) Pet friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&amenities=PETS) House­boat [](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=HOUSE_BOAT) Cottage [](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=COTTAGE) Apart­ment [](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=APARTMENT) Family friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&travelerType=family_friendly) ## Check prices for these dates Tonight [26 Feb - 27 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2026-02-26&endDate=2026-02-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [27 Feb - 28 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2026-02-27&endDate=2026-02-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [27 Feb - 1 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2026-02-27&endDate=2026-03-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [6 Mar - 8 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestertown hotels ![Private beach nearby, sun-loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/2b5c3ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/c765d8e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/01b06110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach nearby, sun-loungers, beach volleyball](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/b3c72334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Lodge at Great Oak Landing [](https://www.expedia.co.uk/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) Chestertown 7.8/10 Good (77 reviews) "Very nice rooms, " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephania £91 includes taxes & fees 17 Mar - 18 Mar [](https://www.expedia.co.uk/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/799945fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/9028be2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/25360cf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn & Suites Chestertown [](https://www.expedia.co.uk/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) Chestertown 7.2/10 Good (427 reviews) "Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linette £66 includes taxes & fees 27 Feb - 28 Feb [](https://www.expedia.co.uk/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) ![Free daily full breakfast ](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/f2092e85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/3c69f06e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/9a7a154a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Chestertown [](https://www.expedia.co.uk/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) Chestertown 8.6/10 Excellent (879 reviews) "Polite and kind hotel manager" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard £83 includes taxes & fees 15 Mar - 16 Mar [](https://www.expedia.co.uk/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/5bf9cecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/dd688df9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (O'Neill) | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/c3481ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/052f9ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vandiver Inn [](https://www.expedia.co.uk/Havre-De-Grace-Hotels-Vandiver-Inn.h16200162.Hotel-Information) Havre De Grace 9.4/10 Exceptional (536 reviews) "a wonderful place to stay with super friendly staff. easy walks to downtown and restaurants. stayed here before and definitely will be back" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dieter [](https://www.expedia.co.uk/Havre-De-Grace-Hotels-Vandiver-Inn.h16200162.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/49900/49890/650ea886.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/bathtub, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/50000/49900/49890/0a422533.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, soundproofing, rollaway beds](https://images.trvl-media.com/lodging/1000000/50000/49900/49890/a39ec805.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/49900/49890/3a758c3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Havre De Grace Aberdeen Area [](https://www.expedia.co.uk/Havre-De-Grace-Hotels-Super-8-By-Wyndham-Havre-De-Grace-Aberdeen-Area.h49890.Hotel-Information) Havre De Grace 6.6/10 (975 reviews) "There were no healthy options offered, not even hard-boiled eggs. I guess they haven't seen the new food pyramid!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carleen Lyden £43 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Havre-De-Grace-Hotels-Super-8-By-Wyndham-Havre-De-Grace-Aberdeen-Area.h49890.Hotel-Information) ![Free continental breakfast ](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/9b37b4b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, soundproofing, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/1cf6b640.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/81d1d1ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/8c995ed0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express White Marsh by IHG [](https://www.expedia.co.uk/Baltimore-Hotels-Holiday-Inn-Express-White-Marsh.h71532135.Hotel-Information) Nottingham 9.4/10 Exceptional (1,009 reviews) "We loved our stay here! Bed and pillows were clean and comfy, hot breakfast had all the necessities, and rooms were very nice! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Madyn £90 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Baltimore-Hotels-Holiday-Inn-Express-White-Marsh.h71532135.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/75000000/74660000/74651500/74651432/e5cd056f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/75000000/74660000/74651500/74651432/bcb2d6f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/75000000/74660000/74651500/74651432/9a72fb78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/75000000/74660000/74651500/74651432/5b8a755d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TownePlace Suites by Marriott Edgewood Aberdeen [](https://www.expedia.co.uk/TownePlace-Suites-Edgewood-Aberdeen.h74651432.Hotel-Information) Aberdeen 9.2/10 Wonderful (106 reviews) "Clean room and attentive staff ." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen £109 includes taxes & fees 15 Mar - 16 Mar [](https://www.expedia.co.uk/TownePlace-Suites-Edgewood-Aberdeen.h74651432.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/d7f9ddda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/4da4e372.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/8890e17f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/30dd84ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Kent Narrows & Marina [](https://www.expedia.co.uk/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) Grasonville 9.6/10 Exceptional (718 reviews) "Amazing location and staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bobbi J. £90 includes taxes & fees 16 Mar - 17 Mar [](https://www.expedia.co.uk/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/b2a10ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/76d50f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/4973a39f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/028c45ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Grasonville near Kent Island [](https://www.expedia.co.uk/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) Grasonville 7.8/10 Good (875 reviews) "Nice staff and rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Walter £69 includes taxes & fees 15 Mar - 16 Mar [](https://www.expedia.co.uk/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) ![Lake](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/694681d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Woods Cottage | Living area | Flat-screen TV, fireplace](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/ea9c33ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/8889a53b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily local cuisine breakfast ](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/1744d173.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Huntingfield Creek [](https://www.expedia.co.uk/Rock-Hall-Hotels-Inn-At-Huntingfield-Creek.h15600253.Hotel-Information) Rock Hall 10/10 Exceptional (61 reviews) "Quiet. Friendly staff. Beautiful grounds. Very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian [](https://www.expedia.co.uk/Rock-Hall-Hotels-Inn-At-Huntingfield-Creek.h15600253.Hotel-Information) ![Front of property – evening/night](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/49680cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Single Room | Frette Italian sheets, premium bedding, down duvets, pillow-top beds](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/ece40ddc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/462e7c63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Chesapeake Bay Beach Club [](https://www.expedia.co.uk/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) Stevensville 9.4/10 Exceptional (437 reviews) "Amazing rooms and service!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alicia £155 includes taxes & fees 9 Mar - 10 Mar [](https://www.expedia.co.uk/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![In-room safe, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/d2d73c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/355fffa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/65f089c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/3bc97cb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites Aberdeen-Bel Air by IHG [](https://www.expedia.co.uk/Bel-Air-Hotels-Candlewood-Suites-Aberdeen-Edgewood-Bel-Air.h2355869.Hotel-Information) Bel Air 8.0/10 Very good (487 reviews) "The staff is great, roon clean & spacious" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas £69 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Bel-Air-Hotels-Candlewood-Suites-Aberdeen-Edgewood-Bel-Air.h2355869.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/ff957644.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/1bbd1ca0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/61316540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/74da44e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Bel Air [](https://www.expedia.co.uk/Bel-Air-Hotels-Hilton-Garden-Inn-Bel-Air.h65327947.Hotel-Information) Bel Air 9.2/10 Wonderful (245 reviews) "Very friendly staff and easy check in." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kurt £88 includes taxes & fees 5 Mar - 6 Mar [](https://www.expedia.co.uk/Bel-Air-Hotels-Hilton-Garden-Inn-Bel-Air.h65327947.Hotel-Information) ![Desk, iron/ironing board, free cots/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/1f4f5be3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/61b9d981.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/dd2808c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/2b727b85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Baltimore/Essex Area [](https://www.expedia.co.uk/Baltimore-Hotels-Super-8-By-Wyndham-BaltimoreEssex-Area.h49889.Hotel-Information) Essex 5.6/10 (431 reviews) "Mice and all kind of bugs had to buy blankets to sleep on from the people staying there looked like a halfway house very disappointed coming from Expedia I trust your company on all my business trips I will start checking the reviews. Sorry to say but that was a waist of had money." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emanuel £56 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/Baltimore-Hotels-Super-8-By-Wyndham-BaltimoreEssex-Area.h49889.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/3217cd56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/c77ff2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/758b9b05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/1d7c16b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Kent Narrows Inn [](https://www.expedia.co.uk/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) Grasonville 8.0/10 Very good (1,000 reviews) "Nice breakfast, cleanroom. Great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wayne £77 includes taxes & fees 3 Mar - 4 Mar [](https://www.expedia.co.uk/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, River View | Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/4eefada8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/24fa7509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/5139c564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Annapolis East-Kent Island by IHG [](https://www.expedia.co.uk/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) Grasonville 9.2/10 Wonderful (963 reviews) "Clean room, I enjoy staying here every time I'm in the area" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter £78 includes taxes & fees 3 Mar - 4 Mar [](https://www.expedia.co.uk/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Desk, laptop workspace, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/700000/696300/696211/78a61d66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/700000/696300/696211/95ae72cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/700000/696300/696211/d1bf2404.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/700000/696300/696211/aa69ca75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Edgewood/Aberdeen [](https://www.expedia.co.uk/Bel-Air-Hotels-SpringHill-Suites-By-Marriott-EdgewoodAberdeen.h696211.Hotel-Information) Bel Air 8.8/10 Excellent (369 reviews) "Staff was very courteous " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tina £91 includes taxes & fees 6 Mar - 7 Mar [](https://www.expedia.co.uk/Bel-Air-Hotels-SpringHill-Suites-By-Marriott-EdgewoodAberdeen.h696211.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1610000/1608300/1608237/716a9a4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1610000/1608300/1608237/f6ab6350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1610000/1608300/1608237/0d3003b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1610000/1608300/1608237/d20be1bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard Aberdeen at Ripken Stadium [](https://www.expedia.co.uk/Aberdeen-Hotels-Courtyard-Aberdeen-At-Ripken-Stadium.h1608237.Hotel-Information) Aberdeen 8.6/10 Excellent (226 reviews) "Had a very pleasant check in with this hotel. Many restaurants are within a mile of the hotel. Very close to I-95\. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dennis £70 includes taxes & fees 22 Mar - 23 Mar [](https://www.expedia.co.uk/Aberdeen-Hotels-Courtyard-Aberdeen-At-Ripken-Stadium.h1608237.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/2360f1f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/d03cf3e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/56e37930.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 5 AM to 11 PM, pool loungers](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/b307a535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Kent Island Marina [](https://www.expedia.co.uk/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) Grasonville 9.0/10 Wonderful (1,000 reviews) "Staff was friendly and rooms were clean. Beautiful area to visit. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy £87 includes taxes & fees 3 Mar - 4 Mar [](https://www.expedia.co.uk/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/55000000/54930000/54920100/54920016/9e26cec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/55000000/54930000/54920100/54920016/c399bee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/55000000/54930000/54920100/54920016/2456c036.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/55000000/54930000/54920100/54920016/6793924d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Aberdeen [](https://www.expedia.co.uk/Aberdeen-Hotels-Fairfield-Inn-Suites-By-Marriott-Aberdeen.h54920016.Hotel-Information) Aberdeen 9.0/10 Wonderful (313 reviews) "Always consistent and great staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda £90 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Aberdeen-Hotels-Fairfield-Inn-Suites-By-Marriott-Aberdeen.h54920016.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.co.uk/Hotel-Search?startDate=2026-03-12&endDate=2026-03-13®ionId=7215&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=HTG_SPRING_PROMO_7215) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Hotels.d7215.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Hotels.d7215.Travel-Guide-Hotels) ## Stay near popular Chestertown attractions ### Washington College 4.1/5 (45 reviews) Founded in 1782, Washington College is the first college chartered in the sovereign United States. Explore its picturesque campus with historic architecture and Chester River waterfront views. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561000403) ### Historical Society of Kent County Maryland Step inside the Geddes-Piper House, home to Kent County's historical treasures and curated exhibits. Explore Maryland's rich past through intimate galleries and knowledgeable guides who bring local stories to life. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561000400) ### Wilmer Park Nestled along the Chester River, Wilmer Park offers serene waterfront views and a modern playground for families. Bring a picnic to enjoy in the green spaces or time your visit for one of the community concerts. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561000402) ### River Arts Chestertown Chestertown RiverArts celebrates creativity with monthly themed exhibits and workshops. Explore rotating galleries, meet local artists, and time your visit for the spring "Paint the Town" event or October's Studio Tour. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532662298) ### Garfield Center for the Arts at the Prince Theater This historic 1928 theatre offers an intimate setting for plays, music, and lectures in city centre Chestertown. Catch a performance during the Jazz Festival or Short Attention Span Theatre for a memorable evening. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561000401) ### Chestertown Historic District This preserved colonial port town showcases America's maritime heritage through 18th-century architecture. Stroll brick pavements along the Chester River or visit during the annual Tea Party Festival reenactments. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=950929327394992128) ### Crumpton Auction Dixon's Auction at Crumpton showcases thousands of antiques, collectibles, and furniture in weekly discovery auctions. Arrive early to preview treasures and secure a bidder number before the fast-paced action begins. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532662415) ### Roundtop Park Roundtop Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=924439476191731712) ## Learn more about Chestertown Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour. [See all hotels in Chestertown](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-12&endDate=2026-03-13&adults=2®ionId=7215) ![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=900&h=314&p=1&q=high) ## Top Chestertown Hotel Reviews ![Best Western Plus Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg) ### Best Western Plus Hotel & Conference Center 10/10 Excellent "Room was clean and quiet… will definitely return " [](https://expedia.co.uk/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Americas Best Value Inn Edgewood](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/b1bb9d9d_y.jpg) ### Americas Best Value Inn Edgewood 10/10 Excellent "I like the affordability and cleanliness 👍" [](https://expedia.co.uk/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/8051c714_y.jpg) ### La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh 10/10 Excellent "Staff was courteous as usual. Clean facility and well kept grounds" [](https://expedia.co.uk/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) ![Home2 Suites by Hilton Baltimore/White Marsh](https://images.trvl-media.com/lodging/6000000/6000000/5992000/5991951/e611db61_y.jpg) ### Home2 Suites by Hilton Baltimore/White Marsh 10/10 Excellent "Room was spotless " [](https://expedia.co.uk/Baltimore-Hotels-Home2-Suites-By-Hilton-BaltimoreWhite-Marsh.h5991951.Hotel-Information) ![Hampton Inn Baltimore Bayview Campus](https://images.trvl-media.com/lodging/24000000/23840000/23830900/23830804/e92cee9e_y.jpg) ### Hampton Inn Baltimore Bayview Campus 10/10 Excellent "No complaints other than there wasn't any meat (sausage or bacon) at the free breakfast." [](https://expedia.co.uk/Baltimore-Hotels-Hampton-Inn-Baltimore-Bayview-Campus.h23830804.Hotel-Information) ![Hampton Inn Baltimore/White Marsh](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/932b25b8_y.jpg) ### Hampton Inn Baltimore/White Marsh 10/10 Excellent "Everything was superior" [](https://expedia.co.uk/Baltimore-Hotels-Hampton-Inn-BaltimoreWhite-Marsh.h57004.Hotel-Information) ![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/526c2bf4_y.jpg) ### Hampton Inn Baltimore/Glen Burnie 10/10 Excellent "Was nice comfortable bed " [](https://expedia.co.uk/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Perfect location. Clean room, nice amount of space, and friendly staff. " [](https://expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Fairfield Inn & Suites by Marriott White Marsh](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/8434bf12_y.jpg) ### Fairfield Inn & Suites by Marriott White Marsh 10/10 Excellent "Room was clean and environment was great. " [](https://expedia.co.uk/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information) ## More cheap stays in Chestertown ![Americas Best Value Inn Edgewood](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/b1bb9d9d_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Americas Best Value Inn Edgewood 1709 Edgewood Road Edgewood MD £42 1 Mar - 2 Mar includes taxes & fees 5.8/10 (1,000 reviews) [](https://expedia.co.uk/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information) ![Quality Inn & Suites Bel Air I-95 Exit 77A](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn & Suites Bel Air I-95 Exit 77A 2112a Emmorton Park Road Edgewood MD £48 1 Mar - 2 Mar includes taxes & fees 7.4/10 Good! (1,056 reviews) [](https://expedia.co.uk/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information) ![Comfort Inn & Suites Aberdeen near APG](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/0fca1b7b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Comfort Inn & Suites Aberdeen near APG 980 Hospitality Way Aberdeen MD £61 8 Mar - 9 Mar includes taxes & fees 8/10 Very Good! (853 reviews) [](https://expedia.co.uk/Aberdeen-Hotels-Comfort-Inn-Suites-Aberdeen-Near-APG.h1395595.Hotel-Information) ![Hampton Inn & Suites Edgewood/Aberdeen-South](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn & Suites Edgewood/Aberdeen-South 2110 Emmorton Park Rd Edgewood MD £67 9 Mar - 10 Mar includes taxes & fees 9.2/10 Wonderful! (1,000 reviews) [](https://expedia.co.uk/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) ![Best Western Plus Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Best Western Plus Hotel & Conference Center 5625 O'Donnell Street Baltimore MD £80 1 Mar - 2 Mar includes taxes & fees 7.8/10 Good! (1,002 reviews) [](https://expedia.co.uk/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Fairfield Inn & Suites by Marriott White Marsh](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/8434bf12_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Fairfield Inn & Suites by Marriott White Marsh 8477 Cordon Way Baltimore MD £86 5 Mar - 6 Mar includes taxes & fees 8.6/10 Excellent! (1,001 reviews) [](https://expedia.co.uk/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information) ## Find out more about Chestertown ### Top reasons to visit Chestertown - **Historic Charm:** Explore the picturesque streets adorned with colonial architecture, reflecting Chestertown's rich history. - **Outdoor Activities:** Enjoy a variety of outdoor pursuits, from boating at Tolchester Marina to leisurely strolls along scenic waterfronts. - **Beautiful Parks:** Relax in local parks and picnic areas, perfect for family gatherings amidst nature. - **Vibrant Community:** Experience the warm hospitality of Chestertown, with welcoming accommodations for all types of travellers. - **Scenic Beauty:** Revel in the stunning landscapes of the Eastern Shore, ideal for a relaxing getaway. ### Find great hotels near Chestertown Discover a charming selection of hotels in Chestertown, Maryland, perfect for every traveller. Whether you're seeking pet-friendly accommodations, business-themed stays, or LGBTQIA welcoming environments, Chestertown offers a variety of options to suit your needs. With its picturesque surroundings and warm hospitality, you're sure to find the best Chestertown hotels that provide a memorable vacation experience. - **[Quality Inn & Suites Bel Air I-95 Exit 77A: ](https://www.expedia.co.uk/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information)** Ideal for business travellers, Quality Inn & Suites Bel Air I-95 Exit 77A combines comfort with functionality. Located 13.0km from Chestertown, this hotel offers a range of services tailored to meet the needs of professionals on the go. Guests appreciate the well-equipped business centre, complimentary Wi-Fi, and meeting facilities. The hotel’s spacious rooms are designed for relaxation after a busy day, making it a perfect retreat for those looking to balance work and leisure. - **[Red Roof Inn Aberdeen: ](https://www.expedia.co.uk/Aberdeen-Hotels-Red-Roof-Inn-Aberdeen.h12576.Hotel-Information)** Embracing inclusivity, Red Roof Inn Aberdeen is a welcoming haven for LGBTQIA travellers and their furry companions. Located 13.7km from Chestertown, this hotel is committed to providing a safe and friendly environment. It accommodates pets with specific policies in place, ensuring both human and animal guests feel at home. The property is known for its comfortable rooms and convenience, making it an ideal choice for those seeking a pet-friendly stay that celebrates diversity. - **[Americas Best Value Inn Edgewood: ](https://www.expedia.co.uk/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information)** Situated 13.0km from Chestertown, Americas Best Value Inn Edgewood is a charming option for pet owners looking for affordable lodging. This hotel allows pets and offers a friendly atmosphere for both guests and their four-legged friends. With flexible pet policies and comfortable rooms, it caters to those who appreciate convenience without compromising on quality. Guests enjoy easy access to local attractions while feeling at home in this welcoming environment. ### Where to stay in and around Chestertown Chestertown, Maryland, offers a delightful blend of historical charm and outdoor adventures. Explore the picturesque streets lined with colonial architecture, or head to the nearby Tolchester Marina for a day of boating on the Chesapeake Bay. The Eastern Shore’s scenic beauty provides a perfect backdrop for family-friendly activities, making it an ideal destination for those seeking relaxation and friendly encounters. Discover the unique vibes of this charming town and its surrounding areas during your visit. - **[Worton: ](https://www.expedia.co.uk/Worton-Hotels.d3000440948.Travel-Guide-Hotels)** Located a mere 2.5km from Chestertown, Worton offers a delightful escape for outdoor enthusiasts and nature lovers. The town boasts scenic landscapes, perfect for leisurely walks and picnics. Visitors flock here during spring and summer months for its vibrant recreational areas, including nearby beaches and marinas. Notable attractions include a national state park that invites exploration and adventure, making it an ideal spot for those wishing to soak in Maryland's natural beauty. - **[Georgetown: ](https://www.expedia.co.uk/Georgetown-Hotels.d553248635975874069.Travel-Guide-Hotels)** Nestled within the vicinity of Chestertown, Georgetown is a charming village that attracts visitors with its outdoor experiences and romantic settings. Peak travel times occur during the warm summer months, when guests can enjoy various recreational activities. The village is home to a sports facility stadium and access to a national state park, both of which are perfect for those seeking an active holiday. The quaint atmosphere combined with adventurous pursuits makes Georgetown a lovely addition to your itinerary. - **[Tolchester Beach: ](https://www.expedia.co.uk/Tolchester-Beach-Hotels.d553248635975848245.Travel-Guide-Hotels)** This picturesque village, located close to Chestertown, is a hidden gem for beach lovers and outdoor adventurers alike. Tolchester Beach sees a consistent flow of visitors, particularly in late spring and summer. The scenic boardwalk along the beach invites leisurely strolls, while the proximity to marinas and a national state park enhances its appeal. With its inviting atmosphere and beautiful landscapes, Tolchester Beach is perfect for a relaxing day by the water or an adventure-filled outing. ### Things to do in and around Chestertown Chestertown, Maryland, offers a delightful blend of outdoor activities and scenic beauty, perfect for a relaxing holiday. Visitors can enjoy educational experiences, explore recreational areas, and stroll along the picturesque boardwalk. A highlight for families and friends is the picnic area, ideal for enjoying a leisurely meal amidst nature. Chestertown promises a charming getaway filled with enjoyable activities and beautiful landscapes. **Shopping** In Chestertown, you can enjoy quaint shops for unique gifts. If you're up for a drive, visit Queenstown Premium Outlets for a variety of brands, 10.6km away, or explore Westown, a family-friendly shopping centre, 14.9km away, offering a great mix of stores. **Recreation** Experience the energetic atmosphere at Ripken Stadium, only 13.7km from Chestertown, where you can enjoy various sporting events. Alternatively, Queenstown Harbor Golf Club and Queenstown Harbor Golf Links, both 10.6km away, offer stunning outdoor settings for a round of golf amidst beautiful landscapes. **Adventure** Explore the Emmorton Recreation & Tennis Center, 14.9km from Chestertown, for thrilling tennis matches and recreational activities. Experience the Annapolis Sailing School, 17.4km away, where you can enjoy sailing lessons amidst scenic waters. Alternatively, head to the Tose Family Tennis Center, also 17.4km distant, for more tennis excitement. **Nightlife** In Chestertown, the Garfield Center for the Arts at the Prince Theatre offers a vibrant cultural experience, while the nearby Church Hill Theatre and Everett Theatre provide additional entertainment options, all featuring a charming atmosphere perfect for families and couples seeking a delightful night out. ### Booking tips and Expedia advantages for Chestertown To save money on your trip to Chestertown, consider visiting during the off-peak months of January to February or November, when accommodation rates are lower. Booking your stay on a Tuesday can also yield savings compared to weekends. Use Expedia’s search tool to find budget-friendly hotel options, and don't forget to check for military discounts. Combine your hotel with flights and activities for additional savings. For free activities, explore the charming town and its scenic waterfront. Planning your visit during these times can significantly enhance your budget while enjoying Chestertown's offerings. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Chestertown are January to February and November, where the prices are slightly lower. This is in comparison to June to July and October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Chestertown is Tuesday. The most expensive day to stay in Chestertown is Saturday. - **Find cheap hotels on Expedia:** Utilise Expedia’s search tool to refine your preferences such as budget, desired location, and the type of hotel you favour. To discover the most affordable prices and offers, arrange the price filter from lowest to highest. - **Consider bundling your trip:** You can save money by combining your hotel stay in Chestertown with your flights and activities through an Expedia package. ### Find the best attractions in Chestertown Chestertown offers a delightful blend of outdoor activities and scenic beauty, making it perfect for a beachside family holiday. Visitors can explore the charming historic district, relax in local parks, and enjoy the picturesque waterfront. For those keen on outdoor adventures, the area boasts beautiful beaches and urban parks, providing ample opportunities for relaxation and recreation amidst stunning surroundings. - **Washington College:** Nestled in the heart of Chestertown, Washington College boasts a rich history and vibrant campus life, offering a unique blend of academic excellence and cultural events. Stroll through its picturesque grounds and enjoy the charming architecture that reflects its storied past. - **Rolphs Wharf Marina:** For those seeking adventure, Rolphs Wharf Marina is a haven for outdoor enthusiasts. Engage in various water activities, relax by the beach, or simply soak in the stunning views of the Chester River, making it an ideal spot for a day of exploration. - **Historical Society of Kent County Maryland:** Immerse yourself in the local heritage at the Historical Society of Kent County Maryland. This museum offers fascinating exhibits that illuminate the region's history, culture, and traditions, providing a deeper understanding of Chestertown's past. ### Best time to go to Chestertown The best time to visit Chestertown is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 34.2°F (1.2°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | February | 36.9°F (2.7°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | March | 43.7°F (6.5°C) | Light Rain | Mostly Sunny | Average | Average | | April | 54.3°F (12.4°C) | Light Rain | Mostly Sunny | Slightly High | Average | | May | 63.7°F (17.6°C) | Light Rain | Mostly Sunny | Average | Average | | June | 72.1°F (22.3°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | July | 77.4°F (25.2°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | August | 75.6°F (24.2°C) | Light Rain | Mostly Sunny | Average | Slightly High | | September | 69.4°F (20.8°C) | Light Rain | Mostly Sunny | Average | Average | | October | 59.2°F (15.1°C) | Light Rain | Mostly Sunny | Average | Average | | November | 47.3°F (8.5°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | December | 40.1°F (4.5°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | ### The nearest major airports for your trip to Chestertown To reach Chestertown, Maryland, tourists can fly into several major airports. Washington, DC ([DCA](https://www.expedia.co.uk/Ronald-Reagan-Washington-National-Airport-Hotels.0-aDCA-0.Travel-Guide-Filter-Hotels) \- Ronald Reagan Washington National) is situated 36.0km away, with luxurious hotels like [Salamander Washington DC](https://www.expedia.co.uk/Washington-Hotels-Salamander-Washington-DC.h1044257.Hotel-Information) and InterContinental Washington D.C. - The Wharf, both only 1.2km from the airport. Baltimore, MD ([BWI](https://www.expedia.co.uk/Baltimore-Washington-Intl-Thurgood-Marshall-Airport-Hotels.0-aBWI-0.Travel-Guide-Filter-Hotels) \- Baltimore Washington International Thurgood Marshall) is closer at 31.2km, featuring exquisite options such as [Sagamore Pendry Baltimore](https://www.expedia.co.uk/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information) and [The Ivy Hotel](https://www.expedia.co.uk/Baltimore-Hotels-The-Ivy-Hotel.h9343273.Hotel-Information). Alternatively, Baltimore, MD (MTN - Martin State) is 12.4km away, offering accommodations like [Canopy by Hilton Baltimore Harbor Point](https://www.expedia.co.uk/Baltimore-Hotels-Canopy-By-Hilton-Baltimore-Harbor-Point.h45976006.Hotel-Information) and [Hyatt Place Baltimore Inner Harbor](https://www.expedia.co.uk/Baltimore-Hotels-Hyatt-Place-Baltimore-Inner-Harbor.h8842065.Hotel-Information). Each airport provides convenient access to the respective hotels for a comfortable stay. ## Frequently asked questions ### What is the best area to stay in Chestertown? > This charming area is the heart of Chestertown, known for its beautifully preserved 18th-century architecture and tree-lined streets. It's very walkable, with most shops, restaurants, and attractions clustered around the main thoroughfares. The Chestertown Marina and the scenic waterfront along the Chester River are also just a short stroll away. > > > For couples looking for a romantic getaway, staying in downtown Chestertown offers a delightful experience. You'll find boutique hotels and historic inns that provide a cosy base, with easy access to art galleries, antique shops, and fine dining. Enjoy an evening walk along the waterfront or catch a performance at the local theatre. > > > Solo travellers will also appreciate the convenience and character of downtown. Everything you need is within walking distance, from independent bookstores to coffee shops, making it easy to explore at your own pace and connect with the local community. ### What are the best hotels in Chestertown that travellers recommend? > The Comfort Inn & Suites Chestertown, with an 8.6 rating, is frequently praised by guests for its comfortable and clean rooms and beds. Travellers also highlight the friendly and helpful staff, particularly at the front desk, and the nice, free breakfast. > > > Another highly recommended option is the 3.5-star The Lodge at Great Oak Landing, which has an 8.0 rating. Guests often comment on the friendly and helpful staff, the excellent food at the on-site restaurant, and the perfect, comfortable rooms. This hotel also features an on-site golf course, water and marina views, and a great pool area with umbrellas and sun loungers. ### What are the best family hotels in Chestertown? > The Comfort Inn & Suites Chestertown, with an 8.6 rating, is highly regarded by guests for its comfortable and clean rooms, as well as its friendly and helpful staff. The hotel offers a pool, sofa beds, and cribs, suiting families. Guests also appreciate the complimentary and nice breakfast provided. > > > Another great option is the 3.5-star Lodge at Great Oak Landing, which has an 8.0 rating. This hotel features a pool, connecting rooms, and a playground for children, making it very suitable for families. Guests consistently praise the friendly and helpful staff, the great restaurant with excellent food, and the comfortable rooms. The property also boasts water and marina views, along with pool umbrellas and sun loungers for relaxation. ### What hotels in Chestertown offer free breakfast? > This highly-rated hotel, with an 8.6 review score, provides a free full breakfast, which guests often describe as nice. It also offers other convenient amenities such as free internet, complimentary WiFi, and free self-parking. Guests consistently praise the comfortable and clean rooms and beds, as well as the friendly and helpful staff. The hotel is conveniently located just 1.1 kilometres from Chestertown Dog Park and Rolling Road Park. ### What are the top pet-friendly hotels in Chestertown? > The Comfort Inn & Suites Chestertown, with an 8.6 rating, is a highly recommended 3-star option. This hotel permits pets and offers early check-in, free breakfast, and free full breakfast. Guests frequently mention the comfortable and clean rooms, the friendly and helpful staff, and the comfortable beds. It is conveniently located near Chestertown Dog Park and Rolling Road Park, both just 1.1 km away. > > > Another great choice is the Red Roof Inn & Suites Chestertown, rated 7.2\. This hotel also permits pets, including both dogs and cats. Guests have praised the comfortable and clean rooms, the nice staff, and the easy parking. It is within 1 km of Chestertown Dog Park and Rolling Road Park. > > > The Driftwood Inn is another pet-friendly option, providing free toiletries, free self-parking, and free WiFi. Guests often highlight the clean rooms and friendly staff. It is well-situated for exploring local arts and nature, being 1.6 km from the Garfield Centre for the Arts at the Prince Theater, 1.5 km from River Arts Chestertown, and 2.0 km from Wilmer Park. ### What are the best budget hotels in Chestertown? > The Comfort Inn & Suites Chestertown, with an 8.6 rating, offers comfortable and clean rooms with free WiFi and toiletries. Guests consistently praise the friendly and helpful staff, as well as the nice complimentary breakfast. It is conveniently located near Chestertown Dog Park and Rolling Road Park, both just over 1 km away. > > > Another suitable choice is the Red Roof Inn & Suites Chestertown, rated 7.2\. This hotel also provides comfortable and clean rooms, free WiFi, and complimentary toiletries. Guests often mention the friendly staff and easy parking. It is situated approximately 1 km from Chestertown Dog Park and Rolling Road Park. ### What are the most romantic hotels in Chestertown for couples? > This 3.5-star lodge, with a rating of 8.0, offers a delightful setting with many rooms providing marina and water views, great for a romantic stay. Guests frequently praise the friendly and helpful staff, as well as the excellent food served at the on-site restaurant. The comfortable rooms also contribute to a great experience. The property features a shared, secured pool with umbrellas and sun loungers, and some rooms include a furnished balcony, ideal for enjoying the picturesque surroundings together. ### What are the best hotels in Chestertown near Wilmer Park? > The Driftwood Inn offers child-friendly window designs, ensuring a safe stay for families. Guests appreciate the complimentary toiletries, free self-parking, and free WiFi access. It is located 2.0 km from Wilmer Park, making it a convenient choice for those wishing to visit the park. Guests consistently praise the clean rooms and friendly staff. ### When is the best time to go to Chestertown? > Spring offers mild temperatures, making it ideal for exploring the historic streets and enjoying outdoor activities along the Chester River. The Chestertown Tea Party Festival in May is a popular annual event, reenacting the 1774 protest and featuring a parade, historic crafts, and tall ship tours. This period is particularly good for families looking for engaging historical experiences. > > > Autumn brings cooler weather and beautiful fall foliage, especially along the riverfront and surrounding countryside. The Chestertown Harry Potter Festival in September draws many visitors with themed activities, street performers, and a "Quidditch" tournament. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Chestertown hotel booking with Expedia? ### How much is the nightly rate at a Chestertown hotel? ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - More ways to book - [Cheap Hotels in Aberdeen ](https://www.expedia.co.uk/Aberdeen-Hotels-Budget-Hotels.0-0-d6044-tBudgetHotels.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Aberdeen ](https://www.expedia.co.uk/Aberdeen-Hotels-Gay-Friendly-Hotel.0-0-d6044-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Aberdeen ](https://www.expedia.co.uk/Aberdeen-Hotels-Hotel-With-Early-Check-In.0-0-d6044-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with Entertainment in Aberdeen ](https://www.expedia.co.uk/Aberdeen-Hotels-Hotel-With-Entertainment.0-0-d6044-thotelwithentertainment.Travel-Guide-Filter-Hotels) - 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