Title: Hotels in Chestertown, MD - Best Chestertown Hotels from £43 - Fully Refundable Options - 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/aerial-view-historic-waterfront-town-river-bridge-autumn.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find hotels in Chestertown, MD from £43 - ![](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=2026-01-25&d1=2026-01-25&endDate=2026-01-27&d2=2026-01-27&amenities=POOL) 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=2026-01-25&d1=2026-01-25&endDate=2026-01-27&d2=2026-01-27&amenities=PETS) 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=2026-01-25&d1=2026-01-25&endDate=2026-01-27&d2=2026-01-27&amenities=HOT_TUB) 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=2026-01-25&d1=2026-01-25&endDate=2026-01-27&d2=2026-01-27&lodging=APARTMENT) 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=2026-01-25&d1=2026-01-25&endDate=2026-01-27&d2=2026-01-27&lodging=COTTAGE) 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=2026-01-25&d1=2026-01-25&endDate=2026-01-27&d2=2026-01-27&travelerType=family_friendly) Waterpark [](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=2026-01-25&d1=2026-01-25&endDate=2026-01-27&d2=2026-01-27&amenities=WATER_PARK) ## Check prices for these dates Tonight [11 Jan - 12 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2026-01-11&endDate=2026-01-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [12 Jan - 13 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2026-01-12&endDate=2026-01-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [16 Jan - 18 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [23 Jan - 25 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestertown hotels ![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) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/25360cf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/cbce9d0c.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 (426 reviews) "Clean and friendly staff. Good location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert £60 includes taxes & fees 17 Jan - 18 Jan [](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) ![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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/b0d84a77.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) ### Comfort Inn & Suites Chestertown [](https://www.expedia.co.uk/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) Chestertown 8.6/10 Excellent (866 reviews) "Everything was well!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ahmed £84 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Standard Room, 2 Queen Beds | In-room safe, desk, soundproofing, rollaway beds](https://images.trvl-media.com/lodging/1000000/50000/49900/49890/dfe7d9ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Vending machine](https://images.trvl-media.com/lodging/1000000/50000/49900/49890/a6e6b250.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) ![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 (969 reviews) "It's was satisfactory " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John £44 includes taxes & fees 18 Jan - 19 Jan [](https://www.expedia.co.uk/Havre-De-Grace-Hotels-Super-8-By-Wyndham-Havre-De-Grace-Aberdeen-Area.h49890.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) ![Room, Private Bathroom (Tydings) | Premium bedding, memory-foam beds, desk, iron/ironing board](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/727c3c6a.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) ![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) ### Vandiver Inn [](https://www.expedia.co.uk/Havre-De-Grace-Hotels-Vandiver-Inn.h16200162.Hotel-Information) Havre De Grace 9.4/10 Exceptional (533 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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/700000/696300/696211/5a18ae7f.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/700000/696300/696211/d1bf2404.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 (364 reviews) "I usually like staying at SpringHill Suites locations. While this location was absolutely clean, quiet and the staff was great, the facility itself was a bit run down- cracks in the sink, etc. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katharine £92 includes taxes & fees 19 Jan - 20 Jan [](https://www.expedia.co.uk/Bel-Air-Hotels-SpringHill-Suites-By-Marriott-EdgewoodAberdeen.h696211.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) ![Exterior](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/ca9c2666.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 (238 reviews) "Kind staff, very clean. Lovely stay!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Michelle £82 includes taxes & fees 23 Jan - 24 Jan [](https://www.expedia.co.uk/Bel-Air-Hotels-Hilton-Garden-Inn-Bel-Air.h65327947.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/951120d2.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/f9e9188e.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/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/3000000/2360000/2355900/2355869/3bc97cb5.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 (478 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 14 Jan - 15 Jan [](https://www.expedia.co.uk/Bel-Air-Hotels-Candlewood-Suites-Aberdeen-Edgewood-Bel-Air.h2355869.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) ![Property grounds](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/f2afc3df.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 (59 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) ![Reception](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/f2cc9e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a0732bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Single Room, Balcony | Terrace/patio](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/2f6490c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Single Room, 1 King Bed | Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a98cfc15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kent Island Resort [](https://www.expedia.co.uk/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) Stevensville 9.2/10 Wonderful (130 reviews) "Beautiful and peaceful property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jerry £131 includes taxes & fees 18 Jan - 19 Jan [](https://www.expedia.co.uk/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.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) ![View from property](https://images.trvl-media.com/lodging/75000000/74660000/74651500/74651432/7daf57ab.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) ![Private kitchen](https://images.trvl-media.com/lodging/75000000/74660000/74651500/74651432/9a72fb78.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 9.0/10 Wonderful (101 reviews) "Clean room and attentive staff ." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen £99 includes taxes & fees 12 Jan - 13 Jan [](https://www.expedia.co.uk/TownePlace-Suites-Edgewood-Aberdeen.h74651432.Hotel-Information) ![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/ead5e21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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 (867 reviews) "Great hotel. Stayed multiple times at this location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas £70 includes taxes & fees 19 Jan - 20 Jan [](https://www.expedia.co.uk/Grasonville-Hotels-Quality-Inn.h190683.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) ![Lobby](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/9e72db94.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) ![Exterior](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/8890e17f.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 (698 reviews) "Good breakfast, great view, clean and well run, pleasant staff, great dining options nearby. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin £100 includes taxes & fees 19 Jan - 20 Jan [](https://www.expedia.co.uk/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/5139c564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/8e62a1db.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) ### 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 (950 reviews) "Great staff, clean room, nice view!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Quiana £79 includes taxes & fees 24 Jan - 25 Jan [](https://www.expedia.co.uk/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.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) ![Garden](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/0fbfe277.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) ![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) ### 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 (433 reviews) "Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rery £156 includes taxes & fees 18 Jan - 19 Jan [](https://www.expedia.co.uk/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774553/f058e662.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774553/2279c753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774553/cf0869c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2780000/2774600/2774553/418e7e85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Bel Air [](https://www.expedia.co.uk/Bel-Air-Hotels-Homewood-Suites-By-Hilton-Bel-Air.h2774553.Hotel-Information) Bel Air 8.8/10 Excellent (450 reviews) "Very welcoming stuff. Clean room at the exception of the Sofa, it has pets hair!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Mohamed £78 includes taxes & fees 17 Jan - 18 Jan [](https://www.expedia.co.uk/Bel-Air-Hotels-Homewood-Suites-By-Hilton-Bel-Air.h2774553.Hotel-Information) ![Free daily continental breakfast ](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/2b57d3ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds, Accessible, Non Smoking (Hearing Impaired) | In-room safe, desk, laptop workspace, free WiFi](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/0dcd9442.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast ](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/4e1cb5a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, free WiFi](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/01d6367e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Baltimore/Glen Burnie [](https://www.expedia.co.uk/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information) Glen Burnie 8.2/10 Very good (1,003 reviews) "Staff is friendly, efficient and kind. Also when I had an issue with the room, it was fixed promptly and staff was very apologetic and again just overall friendly and wonderful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Harriet £76 includes taxes & fees 19 Jan - 20 Jan [](https://www.expedia.co.uk/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.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) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/20000/11300/11278/bb752da8.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 (1,002 reviews) "Nice breakfast, cleanroom. Great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wayne £69 includes taxes & fees 18 Jan - 19 Jan [](https://www.expedia.co.uk/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1160000/1157700/1157601/ded01dfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1160000/1157700/1157601/09e8a3b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 Queen Bed, Accessible, Non Smoking | Private kitchen | Full-sized fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1160000/1157700/1157601/ea0d632a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1160000/1157700/1157601/bc5209ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Extended Stay America Suites Baltimore Bel Air Aberdeen [](https://www.expedia.co.uk/Bel-Air-Hotels-Extended-Stay-America-Suites-Baltimore-Bel-Air-Aberdeen.h1157601.Hotel-Information) Bel Air 7.0/10 Good (712 reviews) "Reasonable for the location . " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shannandoah £62 includes taxes & fees 14 Jan - 15 Jan [](https://www.expedia.co.uk/Bel-Air-Hotels-Extended-Stay-America-Suites-Baltimore-Bel-Air-Aberdeen.h1157601.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/1c3a6583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/96c882ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/fa561265.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Yoga](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/cfd029ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD [](https://www.expedia.co.uk/Bel-Air-Hotels-Country-Inn-Suites-By-Radisson.h891451.Hotel-Information) Bel Air 8.8/10 Excellent (1,006 reviews) "We found the overall hotel and surrounding area very nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacquelyn £68 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Bel-Air-Hotels-Country-Inn-Suites-By-Radisson.h891451.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/24000000/23690000/23686900/23686806/d7725583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/24000000/23690000/23686900/23686806/e3e5e599.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/24000000/23690000/23686900/23686806/32f4f420.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/24000000/23690000/23686900/23686806/9cf8fed6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites Baltimore White Marsh/Middle River [](https://www.expedia.co.uk/Baltimore-Hotels-SpringHill-Suites-Baltimore-White-MarshMiddle-River.h23686806.Hotel-Information) Middle River 9.0/10 Wonderful (783 reviews) "Thank you for another great stay at Spring Hill Suites" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa £92 includes taxes & fees 18 Jan - 19 Jan [](https://www.expedia.co.uk/Baltimore-Hotels-SpringHill-Suites-Baltimore-White-MarshMiddle-River.h23686806.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=2026-01-25&endDate=2026-01-26®ionId=7215&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](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) Enjoy the student vibe when you visit Washington College during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561000403) ### Wilmer Park Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561000402) ### Historical Society of Kent County Maryland You can spend an afternoon browsing the exhibits at Historical Society of Kent County Maryland during your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561000400) ### River Arts Chestertown Enjoy the student vibe when you visit River Arts Chestertown during your trip to Chestertown. Take in the festivals in this family-friendly area. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532662298) ### Chestertown Historic District Find out about the history of Chestertown with a stop at Chestertown Historic District. Experience the area's festivals and art scene. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=950929327394992128) ### Rolphs Wharf Marina Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561879605) ### 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) ### Crumpton Auction Take the family on an outing to Crumpton Auction during your trip to Chestertown. Take in the festivals while you're in the area. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532662415) ## 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=2026-01-25&endDate=2026-01-26&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 ![Hampton Inn & Suites Edgewood/Aberdeen-South](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5_y.jpg) ### Hampton Inn & Suites Edgewood/Aberdeen-South 10/10 Excellent "Profesional staff. Verry clean room. Nice break fast." [](https://expedia.co.uk/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.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 "H" [](https://expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Quality Inn & Suites Bel Air I-95 Exit 77A](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76_y.jpg) ### Quality Inn & Suites Bel Air I-95 Exit 77A 10/10 Excellent "Everything was clea" [](https://expedia.co.uk/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information) ![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 "Front desk staff and breakfast staff" [](https://expedia.co.uk/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Pendry Baltimore](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg) ### Pendry Baltimore 10/10 Excellent "The hotel was beautiful, and the staff was courteous and friendly. " [](https://expedia.co.uk/Baltimore-Hotels-Pendry-Baltimore.h17395897.Hotel-Information) ![Annapolis Waterfront Hotel, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg) ### Annapolis Waterfront Hotel, Autograph Collection 10/10 Excellent "Very welcoming and room very clean." [](https://expedia.co.uk/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Hilton Garden Inn Baltimore/White Marsh](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/09307c3d_y.jpg) ### Hilton Garden Inn Baltimore/White Marsh 10/10 Excellent "All was well" [](https://expedia.co.uk/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.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 excellent, room was clean . Nice and quiet " [](https://expedia.co.uk/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.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 "Quiet and clean " [](https://expedia.co.uk/Edgewood-Hotels-Hilltop-Motel.h20063.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 £43 12 Jan - 13 Jan includes taxes & fees 5.6/10 (999 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 £43 25 Jan - 26 Jan includes taxes & fees 7.2/10 Good! (1,021 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 £64 25 Jan - 26 Jan includes taxes & fees 7.8/10 Good! (826 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 £68 17 Jan - 18 Jan includes taxes & fees 9.2/10 Wonderful! (1,002 reviews) [](https://expedia.co.uk/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.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 £83 14 Jan - 15 Jan includes taxes & fees 8.4/10 Very Good! (1,001 reviews) [](https://expedia.co.uk/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.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 £86 18 Jan - 19 Jan includes taxes & fees 7.8/10 Good! (1,001 reviews) [](https://expedia.co.uk/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.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? > For couples seeking a tranquil escape, Great Oak Landing provides a romantic backdrop for quality time together. Imagine sipping coffee on your private balcony while watching the sunrise over the water or enjoying a sunset picnic on the riverbank. The intimate setting is great for creating cherished memories. > > > Families will also appreciate the area, as it combines relaxation with family-friendly activities. The spacious rooms and proximity to local attractions mean there's something for everyone, from exploring the charming town centre to engaging in water sports on the Chester River. ### What are the best hotels in Chestertown that travellers recommend? ### What are the best family hotels in Chestertown? ### What are the best budget hotels in Chestertown? > Another excellent option is the Red Roof Inn & Suites Chestertown, which scores a solid 7.4 in guest reviews. This hotel also provides a friendly setting for families, featuring free cribs and a sofa bed that can accommodate larger groups. The free long-distance calls and in-room internet make it easy to stay connected during your travels. Located in the historical district, this property offers unique charm alongside practicality without breaking the bank. > > > For those interested in a slightly different experience, The Lodge at Great Oak Landing, with a review score of 7.8, caters well to couples and those looking for a scenic getaway. Nestled by the water, it features a shared outdoor pool and beachfront access, great for romantic strolls on the sand. Golf enthusiasts will also find delight in the on-site golf course, adding an adventurous twist to their stay. View all [budget hotels in Chestertown](https://www.expedia.co.uk/Chestertown-Hotels-Budget-Hotels.0-0-d7215-tBudgetHotels.Travel-Guide-Filter-Hotels). ### When is the best time to go to Chestertown? > As you plan your visit, bear in mind that the peak tourist season runs from June to August. This bustling time offers a plethora of activities, from boating on the Chester River to strolling through the lively farmers' market. The atmosphere is electric, with plenty of opportunities for outdoor dining, allowing you to savour local seafood while soaking up the sun. Engaging with the local community at various events can enhance your experience, making it a memorable adventure. > > > For those who prefer a quieter experience, consider visiting Chestertown in the shoulder season of late September or early October. The weather remains pleasant, with temperatures around 22°C, and you can enjoy the stunning autumn foliage without the summer crowds. It's an excellent time for leisurely walks along the river or visiting nearby wineries, where you can indulge in tastings amidst beautiful fall scenery. ### 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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