Title: Best Chestertown Hotels: Less Stress, More Travel | 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) ![Eastern Shore small towns in Maryland, USA. Traveling the Eastern Shore points o f Maryland this weekend, we came across this local church with gravestones. We found several of these local churches along with the many farms and inlets leading to the Chesapeake bay.](https://images.trvl-media.com/place/7215/39d32fed-717d-4f49-ae4c-a7eb875f5cb2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Patricia Knorr # Find hotels in Chestertown, MD from £48 ![](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 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=2025-10-26&d1=2025-10-26&endDate=2025-10-28&d2=2025-10-28&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=2025-10-26&d1=2025-10-26&endDate=2025-10-28&d2=2025-10-28&amenities=HOT_TUB) 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=2025-10-26&d1=2025-10-26&endDate=2025-10-28&d2=2025-10-28&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=2025-10-26&d1=2025-10-26&endDate=2025-10-28&d2=2025-10-28&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=2025-10-26&d1=2025-10-26&endDate=2025-10-28&d2=2025-10-28&travelerType=family_friendly) 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=2025-10-26&d1=2025-10-26&endDate=2025-10-28&d2=2025-10-28&lodging=APARTMENT) 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=2025-10-26&d1=2025-10-26&endDate=2025-10-28&d2=2025-10-28&amenities=WATER_PARK) 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=2025-10-26&d1=2025-10-26&endDate=2025-10-28&d2=2025-10-28&amenities=POOL) ## Check prices for these dates Tonight [12 Oct - 13 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [13 Oct - 14 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [17 Oct - 19 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [24 Oct - 26 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top 10 Chestertown hotels and places to stay ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/959c2292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast ](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/da06d995.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) ### Comfort Inn & Suites Chestertown Chestertown 8.6/10 Excellent (826) "Friendly staff, clean room, convenient location. " £85 includes taxes & fees 19 Oct - 20 Oct [](https://www.expedia.co.uk/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/8b9992bd.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) ![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 Chestertown 7.2/10 Good (402) "We had a great stay with our two Pups.. The room was very nice and comfortable and very clean." £67 includes taxes & fees 19 Oct - 20 Oct [](https://www.expedia.co.uk/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) ![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) ![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) ![Point of interest](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/72a73d25.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) ### The Lodge at Great Oak Landing Chestertown 7.8/10 Good (70) "Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!" £113 includes taxes & fees 14 Oct - 15 Oct [](https://www.expedia.co.uk/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/8051c714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/dfe0704f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/b1fff75b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/5b523daa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh Rosedale 7.0/10 Good (1017) "Had a nice stay " £66 includes taxes & fees 26 Oct - 27 Oct [](https://www.expedia.co.uk/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) ![Desk, free WiFi, bed sheets, alarm clocks](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/abecbdac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast ](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/29162b24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/0c88ebfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn & Suites Bel Air I-95 Exit 77A Edgewood 7.2/10 Good (1007) "Fine would stay again" £52 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/a8fad934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom | Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/6b94b388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Holiday Inn Express Annapolis East-Kent Island by IHG Grasonville 9.2/10 Wonderful (906) "Nice Holiday Inn Express with great water views." £99 includes taxes & fees 10 Nov - 11 Nov [](https://www.expedia.co.uk/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/19c3b260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/58057ff7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/a9a9ef59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Hotel & Conference Center Medford 7.8/10 Good (1001) "Great stay" £94 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/7de3cb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillow-top beds, in-room safe](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/12e4e2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/114f1de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/0c8b9f64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Baltimore North, MD Rossville 7.2/10 Good (1003) "I have been staying here for some time now and I've always been happy and every time I come in they always remember me very welcoming very helpful above and beyond service and always ask how the families doing how I'm doing it's like being home when you're away from home very happy with the place very clean rooms very nice affordable prices and staff does an amazing job working hard on keeping the place clean amazing breakfast rooms are always clean the whole place and the staff and give it a 10... £79 includes taxes & fees 26 Oct - 27 Oct [](https://www.expedia.co.uk/Baltimore-Hotels-Country-Inn-Suites-By-Radisson.h2410000.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/0fca1b7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast ](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/9f4cdea7.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/2000000/1400000/1395600/1395595/4e480368.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/9c87ac97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Aberdeen near APG Aberdeen 7.8/10 Good (777) "Room was clean, price is very reasonable. " £78 includes taxes & fees 10 Nov - 11 Nov [](https://www.expedia.co.uk/Aberdeen-Hotels-Comfort-Inn-Suites-Aberdeen-Near-APG.h1395595.Hotel-Information) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/8434bf12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/ad2aa516.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/0dd46a2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/5d79a398.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott White Marsh Nottingham 8.6/10 Excellent (1007) "I loved EVERYTHING about this hotel!! We will definitely be back" £84 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/b1bb9d9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/ee9bd670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/c1cd1534.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/1c55f3cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Americas Best Value Inn Edgewood Edgewood 5.6/10 (989) "Stayed 3 nights. The beds were comfortable, the rooms were clean. " £48 includes taxes & fees 26 Oct - 27 Oct [](https://www.expedia.co.uk/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86.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) ![Exterior](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/e60ed5ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/bdf87bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Kent Narrows & Marina Grasonville 9.4/10 Exceptional (638) "Great location and rooms. Great place!" £120 includes taxes & fees 21 Oct - 22 Oct [](https://www.expedia.co.uk/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/25ad1d72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/05b80e5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/19cae57c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Edgewood/Aberdeen-South Edgewood 9.4/10 Exceptional (1005) "Love love love this hotel they provided me with excellent care. Also helped me out with late checkout as needed. Great stay booking again very soon " £70 includes taxes & fees 11 Nov - 12 Nov [](https://www.expedia.co.uk/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/5b1966a6.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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/29901fa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kent Island Resort Stevensville 9.2/10 Wonderful (114) "Great INN super nice staff" £183 includes taxes & fees 13 Oct - 14 Oct [](https://www.expedia.co.uk/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/367a733a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/6468097d.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/2000000/1230000/1222200/1222176/66a1e121.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Kent Island Marina Grasonville 9.0/10 Wonderful (1003) "Hotel was great, beautiful location near the water" £122 includes taxes & fees 16 Oct - 17 Oct [](https://www.expedia.co.uk/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/47756559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/0ab02da4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/8dff74ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, individually furnished, desk](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/6d549ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Baltimore/Aberdeen Aberdeen 9.0/10 Wonderful (582) "This Hotel was excellent in all ways. " £82 includes taxes & fees 21 Oct - 22 Oct [](https://www.expedia.co.uk/Aberdeen-Hotels-Hampton-Inn-Suites-BaltimoreAberdeen.h15990289.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/5c9aedf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/be7252cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Inns of Annapolis Historic District 9.0/10 Wonderful (1846) "Perfect location…terrific staff…spacious room with a king sized bed! " [](https://www.expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/180b8972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast ](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/a1cb4d24.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/1000000/60000/50200/50106/e64b8ed6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/60000/50200/50106/5177cf8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Aberdeen MD Aberdeen 7.0/10 Good (850) "Parking was easy. Bed was super comfy. " £53 includes taxes & fees 12 Nov - 13 Nov [](https://www.expedia.co.uk/Aberdeen-Hotels-Super-8-By-Wyndham-Aberdeen-MD.h50106.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/932b25b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/748fa5a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/e0847094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One queen bed suite non smoking | Hypo-allergenic bedding, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/60000/57100/57004/d9f316c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Baltimore/White Marsh Nottingham 7.8/10 Good (1006) "Really enjoyed my stay, the staff were nice." £86 includes taxes & fees 19 Oct - 20 Oct [](https://www.expedia.co.uk/Baltimore-Hotels-Hampton-Inn-BaltimoreWhite-Marsh.h57004.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/24000000/23840000/23830900/23830804/e92cee9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/24000000/23840000/23830900/23830804/07e31512.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/24000000/23840000/23830900/23830804/6a2a39d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/24000000/23840000/23830900/23830804/c2e0423c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Baltimore Bayview Campus Hopkins Bayview 9.0/10 Wonderful (1007) "I loved how polite and efficient the staff was. The hotel was very clean 6nice" £115 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Baltimore-Hotels-Hampton-Inn-Baltimore-Bayview-Campus.h23830804.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=2025-10-26&endDate=2025-10-27®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 [](https://www.expedia.co.uk/Washington-College-Hotels.0-l553248621561000403-0.Travel-Guide-Filter-Hotels) ### 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) [](https://www.expedia.co.uk/Rolphs-Wharf-Marina-Hotels.0-l553248621561879605-0.Travel-Guide-Filter-Hotels) ### 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) [](https://www.expedia.co.uk/River-Arts-Chestertown-Hotels.0-l553248621532662298-0.Travel-Guide-Filter-Hotels) ### 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) [](https://www.expedia.co.uk/Historical-Society-Of-Kent-County-Maryland-Hotels.0-l553248621561000400-0.Travel-Guide-Filter-Hotels) ### 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) [](https://www.expedia.co.uk/Wilmer-Park-Hotels.0-l553248621561000402-0.Travel-Guide-Filter-Hotels) ### 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) [](https://www.expedia.co.uk/Chestertown-Historic-District-Hotels.0-l950929327394992128-0.Travel-Guide-Filter-Hotels) ### 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) [](https://www.expedia.co.uk/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Hotels.0-l553248621561000401-0.Travel-Guide-Filter-Hotels) ### Garfield Center for the Arts at the Prince Theater You can make plans for a show at Garfield Center for the Arts at the Prince Theater on 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=553248621561000401) [](https://www.expedia.co.uk/Kings-Town-Park-Hotels.0-l924439594043392000-0.Travel-Guide-Filter-Hotels) ### Kings Town Park Kings Town 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=924439594043392000) ## 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=2025-10-26&endDate=2025-10-27&adults=2®ionId=7215) ![](https://mediaim.expedia.com/destination/2/6785bfdbe6f67238f03adb254741e2d9.jpg?impolicy=fcrop&w=400&h=400&p=1&q=high) Photo by Assya A ## Top Chestertown Hotel Reviews ![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](//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 "Very nice and clean" [](https://expedia.co.uk/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) ![The Inn at Henderson's Wharf, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/890000/890000/889993/38664fff_y.jpg) ### The Inn at Henderson's Wharf, an Ascend Collection Hotel 10/10 Excellent "Beautiful location and a great stay. Eric at the front desk was great!" [](https://expedia.co.uk/Baltimore-Hotels-The-Inn-At-Hendersons-Wharf.h889993.Hotel-Information) ![Hilton Garden Inn Baltimore/White Marsh](//images.trvl-media.com/lodging/1000000/440000/433700/433663/09307c3d_y.jpg) ### Hilton Garden Inn Baltimore/White Marsh 10/10 Excellent "Our room was great ! Very clean ! Only problem was the blind was broke and the Kurig didn’t work. I advised them at check out ! " [](https://expedia.co.uk/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.Hotel-Information) ![Quality Inn & Suites Bel Air I-95 Exit 77A](//images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76_y.jpg) ### Quality Inn & Suites Bel Air I-95 Exit 77A 10/10 Excellent "Quiet and clean. Not a LOT of parking but enough if you get there before midnight. " [](https://expedia.co.uk/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information) ![Historic Inns of Annapolis](//images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Excellent stay but I never received my wine " [](https://expedia.co.uk/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Sagamore Pendry Baltimore](//images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg) ### Sagamore Pendry Baltimore 10/10 Excellent "Love this hotel! Absolutely beautiful - from the pool on the harbor, to the atrium, to the restaurant - it's truly outstanding. The staff is also incredibly accomodating. I forgot several articles of clothing and they mailed them to me immediately. I highly recommend the Sagamore Pendry!" [](https://expedia.co.uk/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information) ![Best Western Plus Hotel & Conference Center](//images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg) ### Best Western Plus Hotel & Conference Center 10/10 Excellent "Easy access, dmooth check in, felt safe parking, close to port. " [](https://expedia.co.uk/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Comfort Inn & Suites Chestertown](//images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "Nice hotel" [](https://expedia.co.uk/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Hampton Inn Baltimore/Glen Burnie](//images.trvl-media.com/lodging/1000000/10000/2800/2759/526c2bf4_y.jpg) ### Hampton Inn Baltimore/Glen Burnie 10/10 Excellent "Clean and quiet " [](https://expedia.co.uk/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information) ## More cheap stays in Chestertown ![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/526c2bf4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn Baltimore/Glen Burnie 6617 Ritchie Hwy, Glen Burnie, MD £87 2 Nov - 3 Nov includes taxes & fees 8/10 Very Good! (1,005 reviews) [](https://expedia.co.uk/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.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 £94 2 Nov - 3 Nov includes taxes & fees 7.6/10 Good! (1,001 reviews) [](https://expedia.co.uk/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.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 £52 2 Nov - 3 Nov includes taxes & fees 7.2/10 Good! (1,004 reviews) [](https://expedia.co.uk/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.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 £84 2 Nov - 3 Nov includes taxes & fees 8.4/10 Very Good! (1,004 reviews) [](https://expedia.co.uk/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.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 £70 11 Nov - 12 Nov includes taxes & fees 9.2/10 Wonderful! (1,002 reviews) [](https://expedia.co.uk/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) ![SpringHill Suites Baltimore White Marsh/Middle River](https://images.trvl-media.com/lodging/24000000/23690000/23686900/23686806/ac399738_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### SpringHill Suites Baltimore White Marsh/Middle River 6110 Greenleigh Avenue, Middle River, MD £106 13 Oct - 14 Oct includes taxes & fees 9/10 Wonderful! (746 reviews) [](https://expedia.co.uk/Baltimore-Hotels-SpringHill-Suites-Baltimore-White-MarshMiddle-River.h23686806.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? > Great Oak Landing is the premier area to stay in Chestertown, Maryland, highly favoured by our travellers. Nestled along the picturesque Chester River, this serene neighbourhood offers stunning waterfront views and easy access to nature's beauty. Guests can enjoy leisurely strolls along the riverwalk or explore the nearby parks, making it a fantastic spot for outdoor enthusiasts. > > > > 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? > The Lodge at Great Oak Landing is a charming getaway in Chestertown, rated 7.8 by guests. This hotel offers a picturesque setting with an onsite golf course, superb for those looking to enjoy a leisurely game amidst stunning natural surroundings. The attentive staff and inviting space create a lovely retreat for all visitors. ### What are the best family hotels in Chestertown? > The Lodge at Great Oak Landing in Chestertown is a delightful option for families seeking a relaxing getaway. This charming property boasts a refreshing pool, great for kids to splash around and enjoy sunny days, along with a playground that guarantees endless fun for the little ones. Find more [child-friendly accommodations in Chestertown](https://www.expedia.co.uk/Chestertown-Hotels-Family-Friendly-Hotel.0-0-d7215-tFamilyFriendlyHotel.Travel-Guide-Filter-Hotels). ### What are the best budget hotels in Chestertown? > For travellers seeking budget-friendly accommodations in Chestertown, the [Comfort Inn & Suites Chestertown](https://www.expedia.co.uk/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) stands out with an excellent review score of 8.6. This inviting hotel offers a range of family-friendly amenities, including a seasonal outdoor pool and complimentary breakfast, ensuring a delightful start to your day. Families will appreciate the child-friendly window design and the availability of cribs, making it a great choice for those traveling with little ones. Plus, the convenience of free WiFi and self-parking adds to the overall value. > > > > 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? > The most popular time to visit Chestertown is during the vibrant summer months, particularly July. With average temperatures reaching around 28°C, this is when the town truly comes alive with outdoor activities, festivals, and events. The warm weather invites visitors to enjoy the scenic waterfront, explore the charming streets filled with historic architecture, and take part in local celebrations. > > > > 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? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Chestertown hotel for you. ### How can I save on a Chestertown hotel booking with Expedia? > Members always get our best prices. Find our best Chestertown hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings. ### How much is the nightly rate at a Chestertown hotel? > Prices for hotels in Chestertown often vary, but you can find a great deal from £48 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. 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