Title: Book The Best Hotels in Chestertown, MD for 2026 from CA $79 - Fully Refundable Options - Expedia.ca [Vacation Rentals in Chestertown](https://expedia.ca/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.ca/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Chestertown Car Rentals](https://expedia.ca/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.ca/Chestertown.d7215.Destination-Travel-Guides) ![Eastern Shore Maryland, USA is between the Chesapeake bay and Delaware Bay. There are so many farms and fresh produce in this area just 20 minutes from the surrounding water ways. There are also small venues to eat and all have great crabs and crab bisque.](https://images.trvl-media.com/place/7215/6507b0e9-7981-44e0-9a0d-e95b6eb38908.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Patricia Knorr # Find hotels in Chestertown, MD from CA $79 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](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.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-12-27&d1=2025-12-27&endDate=2025-12-29&d2=2025-12-29&amenities=POOL) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-12-27&d1=2025-12-27&endDate=2025-12-29&d2=2025-12-29&amenities=PETS) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-12-27&d1=2025-12-27&endDate=2025-12-29&d2=2025-12-29&lodging=COTTAGE) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-12-27&d1=2025-12-27&endDate=2025-12-29&d2=2025-12-29&amenities=HOT_TUB) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-12-27&d1=2025-12-27&endDate=2025-12-29&d2=2025-12-29&travelerType=family_friendly) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Chestertown%2C+Maryland%2C+United+States+of+America®ionId=7215&latLong=39.218864%2C-76.069&adults=2&startDate=2025-12-27&d1=2025-12-27&endDate=2025-12-29&d2=2025-12-29&lodging=APARTMENT) ## Check prices for these dates Tonight [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-13&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-14&endDate=2025-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestertown hotels ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/959c2292.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) ![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) ### Comfort Inn & Suites Chestertown [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) Chestertown 8.6/10 Excellent (859) "Everything was well!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ahmed CA $140 CA $156 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Suite, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/17533737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/8b9992bd.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.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information) Chestertown 7.2/10 Good (420) "Professional staff, warm greetings clean room " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dr. Nicholas and Mrs. Karen CA $99 CA $110 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/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 [](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) Chestertown 7.8/10 Good (77) "Very nice rooms, " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephania CA $136 CA $156 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/4ed42fd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/44b6c861.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/1af5cb1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/50bc617c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Driftwood Inn [](https://www.expedia.ca/Chestertown-Hotels-Driftwood-Inn.h4862316.Hotel-Information) Chestertown 5.2/10 (175) "Rooms are clean, staf was helpful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daryl CA $87 CA $97 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Chestertown-Hotels-Driftwood-Inn.h4862316.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) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/bb9281c7.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) ### La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh [](https://www.expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) Rossville 7.0/10 Good (1091) "Staff was great and so was breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terri CA $90 CA $104 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.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) ![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/1000000/120000/117000/116919/2c8e8566.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 [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) Grasonville 9.2/10 Wonderful (932) "It was very comfortable and clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $120 CA $133 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/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) ![Junior Suite (2 Queen Beds with Sofa bed)](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/65534781.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) ### Best Western Plus Hotel & Conference Center [](https://www.expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) Medford 7.8/10 Good (1001) "Clean room, great location, very friendly and helpful staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beverly CA $135 CA $158 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.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) ![Indoor pool](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/19cae57c.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) ### Hampton Inn & Suites Edgewood/Aberdeen-South [](https://www.expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) Edgewood 9.2/10 Wonderful (1001) "Room was great staff friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa CA $112 CA $126 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.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) ![Indoor pool](https://images.trvl-media.com/lodging/16000000/16000000/15990300/15990289/b2e70f95.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) ### Hampton Inn & Suites Baltimore/Aberdeen [](https://www.expedia.ca/Aberdeen-Hotels-Hampton-Inn-Suites-BaltimoreAberdeen.h15990289.Hotel-Information) Aberdeen 9.0/10 Wonderful (600) "very pet friendly!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) larry CA $125 CA $139 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Aberdeen-Hotels-Hampton-Inn-Suites-BaltimoreAberdeen.h15990289.Hotel-Information) ![Desk, free WiFi, bed sheets, alarm clocks](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/dd08388b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/22f9fe46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/7f0eab9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/63592edd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn & Suites Bel Air I-95 Exit 77A [](https://www.expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information) Edgewood 7.4/10 Good (1004) "Staff was very friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashlee CA $85 CA $96 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/9c87ac97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1400000/1395600/1395595/c6592633.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) ### Comfort Inn & Suites Aberdeen near APG [](https://www.expedia.ca/Aberdeen-Hotels-Comfort-Inn-Suites-Aberdeen-Near-APG.h1395595.Hotel-Information) Aberdeen 7.8/10 Good (811) "I love this property very quiet and it's convenient to the shopping center and if you want other food it's connected to an IHOP you don't have to go out in the elements " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shelia CA $106 CA $119 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Aberdeen-Hotels-Comfort-Inn-Suites-Aberdeen-Near-APG.h1395595.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) ![Lobby](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/0c8b9f64.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) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/3000000/2410000/2410000/2410000/12e4e2d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Baltimore North, MD [](https://www.expedia.ca/Baltimore-Hotels-Country-Inn-Suites-By-Radisson.h2410000.Hotel-Information) Rossville 7.2/10 Good (1001) "yes" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ronald CA $124 CA $143 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Baltimore-Hotels-Country-Inn-Suites-By-Radisson.h2410000.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/tub, 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 [](https://www.expedia.ca/Aberdeen-Hotels-Super-8-By-Wyndham-Aberdeen-MD.h50106.Hotel-Information) Aberdeen 7.0/10 Good (859) "Nice and clean. Staff was friendly. I had no problems whatsoever, and I would stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shelly CA $73 CA $81 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Aberdeen-Hotels-Super-8-By-Wyndham-Aberdeen-MD.h50106.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/e17d8d11.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) ![Reception](https://images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/6468097d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Kent Island Marina [](https://www.expedia.ca/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) Grasonville 9.0/10 Wonderful (1001) "We stayed overnight, coming to meet some people for a business meeting. Monica at the front desk provided great customer service and was extremely helpful in accommodating us. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony CA $142 CA $158 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.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) ![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/bdf87bb6.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) ### Hyatt Place Kent Narrows & Marina [](https://www.expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) Grasonville 9.6/10 Exceptional (674) "Great view, good ambiance all around" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dianne CA $151 CA $168 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.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) ![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) ![Lounge](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/ee9bd670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/43f330d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Americas Best Value Inn Edgewood [](https://www.expedia.ca/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information) Edgewood 5.6/10 (1000) "I love staying here. The prices are always reasonable, the staff are always so nice & helpful. The area is kept clean there's stores close to this hotel all around so convient! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christeena CA $70 CA $79 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/dd2808c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/0707a932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/2b727b85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/50000/49900/49889/304c53d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Baltimore/Essex Area [](https://www.expedia.ca/Baltimore-Hotels-Super-8-By-Wyndham-BaltimoreEssex-Area.h49889.Hotel-Information) Essex 5.4/10 (412) "The hotel was great the staff was great very clean " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sean CA $96 CA $111 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Baltimore-Hotels-Super-8-By-Wyndham-BaltimoreEssex-Area.h49889.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) ![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) ![Aerial view](https://images.trvl-media.com/lodging/1000000/200000/194200/194102/a0732bf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Single Room, 1 King Bed](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.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) Stevensville 9.2/10 Wonderful (128) "The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $198 CA $268 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.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) ![Business centre](https://images.trvl-media.com/lodging/2000000/1890000/1888500/1888500/7c3be532.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) ![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) ### Fairfield Inn & Suites by Marriott White Marsh [](https://www.expedia.ca/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information) Nottingham 8.6/10 Excellent (1002) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) brian CA $125 CA $145 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Baltimore-Hotels-Fairfield-Inn-Suites-By-Marriott-White-Marsh.h1888500.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/600/507/ef21026e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/600/507/e2e5d244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/600/507/0de2177e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/600/507/5c9bcbb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Aberdeen by IHG [](https://www.expedia.ca/Aberdeen-Hotels-Holiday-Inn-Express-Aberdeen.h507.Hotel-Information) Aberdeen 8.6/10 Excellent (429) "Most comfortable beds and pillows. Great breakfast. Very clean. Would definitely recommend it. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diana CA $151 CA $169 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Aberdeen-Hotels-Holiday-Inn-Express-Aberdeen.h507.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.ca/Hotel-Search?startDate=2025-12-27&endDate=2025-12-28®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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Hotels.d7215.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Hotels.d7215.Travel-Guide-Hotels) ## 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.ca/Hotel-Search?startDate=2025-12-27&endDate=2025-12-28&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) ### Stay near popular Chestertown attractions [](https://expedia.ca/Washington-College-Hotels.0-l553248621561000403-0.Travel-Guide-Filter-Hotels) #### Washington College Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561000403) [](https://expedia.ca/River-Arts-Chestertown-Hotels.0-l553248621532662298-0.Travel-Guide-Filter-Hotels) #### River Arts Chestertown Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532662298) [](https://expedia.ca/Crumpton-Auction-Hotels.0-l553248621532662415-0.Travel-Guide-Filter-Hotels) #### 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://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532662415) [](https://expedia.ca/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 exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561000400) [](https://expedia.ca/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://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561879605) [](https://expedia.ca/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://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561000402) ## 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 CA $70 CA $79 total Dec 15 - Dec 16 includes taxes & fees 5.6/10 (1,000 reviews) [](https://expedia.ca/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 CA $85 CA $96 total Jan 4 - Jan 5, 2026 includes taxes & fees 7.2/10 Good! (1,004 reviews) [](https://expedia.ca/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 CA $106 CA $119 total Dec 24 - Dec 25 includes taxes & fees 7.8/10 Good! (810 reviews) [](https://expedia.ca/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 CA $112 CA $126 total Dec 22 - Dec 23 includes taxes & fees 9.2/10 Wonderful! (1,006 reviews) [](https://expedia.ca/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 CA $125 CA $145 total Dec 17 - Dec 18 includes taxes & fees 8.4/10 Very Good! (1,005 reviews) [](https://expedia.ca/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 CA $135 CA $158 total Dec 21 - Dec 22 includes taxes & fees 7.8/10 Good! (1,000 reviews) [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ## Hotels in Chestertown with star-rating ![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg) 5 Star Hotels 1 properties [](https://expedia.ca/5Star-Chestertown-Hotels.s50-0-d7215.Travel-Guide-Filter-Hotels) ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 2 properties [](https://expedia.ca/4Star-Chestertown-Hotels.s40-0-d7215.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 74 properties [](https://expedia.ca/3Star-Chestertown-Hotels.s30-0-d7215.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 165 properties [](https://expedia.ca/2Star-Chestertown-Hotels.s20-0-d7215.Travel-Guide-Filter-Hotels) ## Find out more about Chestertown ### Top reasons to visit Chestertown - **Scenic Outdoor Adventures:** Experience beautiful landscapes and recreational activities along the picturesque Chester River. - **Charming Downtown:** Stroll along Main Street to discover delightful shops and local attractions. - **Rich Historical Experience:** Explore the town's rich heritage through house tours and historic sites. - **Festive Community Events:** Enjoy lively holiday activities and festivals that showcase the warmth of the community. - **Diverse Accommodation Options:** Find a range of pet-friendly and welcoming stays for all types of travellers. ### Find great hotels near Chestertown Explore a variety of accommodation options in Chestertown, Maryland, where you can find pet-friendly hotels and motels, perfect for business travellers and those seeking an LGBTQIA welcoming environment. Whether you're looking for vacation rentals, suites, or house rentals, Chestertown offers a range of choices to ensure a comfortable and enjoyable stay in this charming riverside town. - **[Quality Inn & Suites Bel Air I-95 Exit 77A: ](https://www.expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information)** A prime choice for business travellers, Quality Inn & Suites Bel Air I-95 Exit 77A combines convenience and professionalism. Located 33.8km from Chestertown, this hotel offers an array of amenities designed to cater to business needs, such as meeting rooms, free Wi-Fi, and a business centre. Guests have praised the comfortable rooms, ideal for unwinding after a busy day of meetings, along with complimentary breakfast options to kickstart their mornings. Its strategic location near major highways makes it an excellent stop for those on the go. - **[La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: ](https://www.expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information)** This welcoming hotel, situated 33.8km from Chestertown, is a haven for pet owners and travellers seeking relaxation. La Quinta Inn & Suites features a pet-friendly policy, allowing dogs and cats to stay with their owners, making it perfect for those travelling with furry friends. Guests appreciate the spacious rooms and complimentary breakfast, which provides a delightful start to their day. The hotel also boasts a convenient location near local attractions and dining options, ensuring an enjoyable and hassle-free stay for all. - **[Red Roof Inn Aberdeen: ](https://www.expedia.ca/Aberdeen-Hotels-Red-Roof-Inn-Aberdeen.h12576.Hotel-Information)** Located 35.4km from Chestertown, Red Roof Inn Aberdeen is a vibrant option for pet-lovers and LGBTQIA-friendly travellers. This hotel not only welcomes pets but also supports an inclusive environment, making it a comfortable choice for all guests. With amenities that allow pets in rooms and a waived fee for service animals, it’s designed with comfort in mind. Guests have highlighted the affordable rates, clean accommodations, and friendly staff, making it a popular choice for those looking for a welcoming getaway. ### Where to stay in and around Chestertown Chestertown, Maryland, offers a delightful blend of outdoor adventures and rich history, perfect for a family-friendly getaway. Explore charming neighbourhoods and discover friendly resorts that capture the essence of hometown holidays. Enjoy the scenic beauty while soaking in the historical atmosphere, making it an ideal destination for a relaxing weekend escape. Experience the warmth of the community during the holiday season and uncover the hidden gems that make Chestertown a must-visit spot. - **[Worton: ](https://www.expedia.ca/Worton-Hotels.d3000440948.Travel-Guide-Hotels)** Located a mere 6.4km from Chestertown, Worton offers a charming escape for those seeking outdoor adventures and stunning scenery. While the number of visitors fluctuates throughout the year, the peak seasons in April to May and July draw in nature enthusiasts eager to explore its recreational areas and nearby national parks. With attractions such as beautiful beaches and marinas, Worton is perfect for a leisurely day of exploration or fun-filled activities on the water. - **[Georgetown: ](https://www.expedia.ca/Georgetown-Hotels.d553248635975874069.Travel-Guide-Hotels)** Nestled in the vicinity of Chestertown, Georgetown is a quaint village that captivates visitors with its romantic outdoor settings and adventurous spirit. The peak tourist months from June to August offer a lively atmosphere, where you can engage in various recreational activities or relax at local recreation centres. Notable landmarks like sports facilities and a stadium enhance the area’s appeal, making it an excellent spot for those looking to combine relaxation with a dash of excitement. - **[Tolchester Beach: ](https://www.expedia.ca/Tolchester-Beach-Hotels.d553248635975848245.Travel-Guide-Hotels)** As a delightful village close to Chestertown, Tolchester Beach is an ideal destination for beach lovers and those yearning for natural beauty. While it experiences consistent visitor numbers throughout the year, summer months from June to August are particularly popular. Enjoy leisurely strolls along the boardwalk or take advantage of the recreational areas and nearby marinas. With its proximity to national parks and serene beaches, Tolchester Beach promises a refreshing getaway filled with outdoor enjoyment. ### Things to do in and around Chestertown Chestertown, Maryland, is perfect for an outdoor getaway, offering beautiful scenery and a range of activities. Visitors can enjoy house tours, explore recreational areas, stroll along the boardwalk, and participate in festival events. The downtown area hosts festive holiday activities, making it an ideal spot for a weekend escape or day trip, ensuring a delightful experience for all who visit. **Shopping** In Chestertown, you can enjoy local shops and boutiques for unique gifts. If you're up for a drive, visit the [Queenstown Premium Outlets](https://www.expedia.ca/Queenstown-Premium-Outlets-Hotels.0-l553248621532662352-0.Travel-Guide-Filter-Hotels), located 27.4km away, for brand-name bargains. [Paul Reed Smith Guitars](https://www.expedia.ca/Paul-Reed-Smith-Guitars-Hotels.0-l747757786500468736-0.Travel-Guide-Filter-Hotels), 33.8km away, offers a unique shopping experience for music enthusiasts. **Recreation** At [Ripken Stadium](https://www.expedia.ca/Ripken-Stadium-Hotels.0-l6145161-0.Travel-Guide-Filter-Hotels), you can immerse yourself in the vibrant sports atmosphere while enjoying various recreational events. Meanwhile, the [Queenstown Harbor Golf Club](https://www.expedia.ca/Queenstown-Harbor-Golf-Club-Hotels.0-l6091731-0.Travel-Guide-Filter-Hotels) and [Queenstown Harbor Golf Links](https://www.expedia.ca/Queenstown-Harbor-Golf-Links-Hotels.0-l553248621532662350-0.Travel-Guide-Filter-Hotels) offer beautiful outdoor settings for a relaxing yet active day on the greens, surrounded by nature's beauty. **Adventure** At the [Annapolis Sailing School](https://www.expedia.ca/Annapolis-Sailing-School-Hotels.0-l553248621532662324-0.Travel-Guide-Filter-Hotels), located 45.1km from Chestertown, you can immerse yourself in thrilling sailing experiences on the beautiful Chesapeake Bay. Alternatively, the Emmorton Recreation & Tennis Center, 38.6km away, offers various engaging recreational activities, while the Tose Family Tennis Center, also 45.1km away, boasts fantastic tennis facilities. **Nightlife** In Chestertown, the [Garfield Center for the Arts at the Prince Theater](https://www.expedia.ca/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Hotels.0-l553248621561000401-0.Travel-Guide-Filter-Hotels) offers vibrant performances in a charming atmosphere. Just a short drive away, [Church Hill Theatre](https://www.expedia.ca/Church-Hill-Theatre-Hotels.0-l844528418122231808-0.Travel-Guide-Filter-Hotels) and [Avalon Theatre](https://www.expedia.ca/Avalon-Theatre-Hotels.0-l6286426-0.Travel-Guide-Filter-Hotels) also provide engaging shows, each with a touch of culture and romance, perfect for a delightful evening out. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Chestertown For a budget-friendly trip to Chestertown, consider visiting between January to February or November for lower accommodation rates. Tuesdays are the cheapest days to stay, while Saturdays tend to be pricier. Use Expedia’s search tool to find budget options, including eco-friendly hotels, and filter by price to uncover the best deals. Additionally, you can save money by bundling your hotel, flights, and activities into an Expedia package. Don’t forget to explore free local attractions to enhance your experience while keeping costs down. - **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:** Utilize Expedia’s search tool to customize your travel preferences, such as your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified option will showcase sustainable and environmentally-friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from lowest to highest. - **Consider bundling your trip:** You can save some money by combining your Chestertown hotel reservation with your flights and activities through an Expedia package. ### Find the best attractions in Chestertown Chestertown, Maryland, offers a delightful mix of outdoor adventures and scenic beauty, perfect for a family beach vacation. Visitors can explore urban parks, marinas, and the picturesque Chester River. A stroll down Main Street Chestertown reveals charming shops and local attractions, making it an ideal destination for those seeking a relaxing getaway in nature. - **[Washington College: ](https://www.expedia.ca/Washington-College-Hotels.0-l553248621561000403-0.Travel-Guide-Filter-Hotels)** Experience the charm of this historic institution, renowned for its picturesque campus and rich cultural heritage. Engage in various events, art exhibitions, and lectures that showcase the vibrant academic community. - **[Rolphs Wharf Marina: ](https://www.expedia.ca/Rolphs-Wharf-Marina-Hotels.0-l553248621561879605-0.Travel-Guide-Filter-Hotels)** Dive into outdoor adventures at this scenic marina. Enjoy kayaking, paddleboarding, or simply relaxing by the water's edge, surrounded by beautiful beach vibes and stunning views of the Chester River. - **[Historical Society of Kent County Maryland: ](https://www.expedia.ca/Historical-Society-Of-Kent-County-Maryland-Hotels.0-l553248621561000400-0.Travel-Guide-Filter-Hotels)** Discover the local history at this engaging museum. Explore fascinating exhibits that highlight the region's past, offering insight into the culture and traditions of Kent County. ### 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 | Average | | 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 | Slightly High | | November | 47.3°F (8.5°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | December | 40.1°F (4.5°C) | Light Rain | Mostly Sunny | Slightly Low | Average | ### The nearest major airports for your trip to Chestertown Chestertown, Maryland, can be conveniently accessed via three major airports. Washington, DC ([DCA](https://www.expedia.ca/Ronald-Reagan-Washington-National-Airport-Hotels.0-aDCA-0.Travel-Guide-Filter-Hotels)\-Ronald Reagan Washington National) is located 93.3km away, with notable hotels like the 5-star InterContinental Washington D.C. - The Wharf and [Riggs Washington DC](https://www.expedia.ca/Washington-Hotels-Riggs-Washington-DC.h37192042.Hotel-Information), both within 4.8km. Baltimore, MD ([BWI](https://www.expedia.ca/Baltimore-Washington-Intl-Thurgood-Marshall-Airport-Hotels.0-aBWI-0.Travel-Guide-Filter-Hotels)\-Baltimore Washington Intl. Thurgood Marshall) is closer at 51.5km, featuring luxurious options such as the [Sagamore Pendry Baltimore](https://www.expedia.ca/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information) and [Four Seasons Hotel Baltimore](https://www.expedia.ca/Baltimore-Hotels-Four-Seasons-Hotel-Baltimore.h4603198.Hotel-Information), both 12.9km from the airport, offering shuttle services. Lastly, Baltimore, MD ([MTN](https://www.expedia.ca/Martin-State-Airport-Hotels.0-aMTN-0.Travel-Guide-Filter-Hotels)\-Martin State) lies 32.2km away, with hotels like [Canopy by Hilton Baltimore Harbor Point](https://www.expedia.ca/Baltimore-Hotels-Canopy-By-Hilton-Baltimore-Harbor-Point.h45976006.Hotel-Information) and [Hyatt Place Baltimore Inner Harbor](https://www.expedia.ca/Baltimore-Hotels-Hyatt-Place-Baltimore-Inner-Harbor.h8842065.Hotel-Information), both around 16.1km from the airport. ## Recent reviews of Chestertown hotels ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 5/5 Excellent "Beautiful area! Loved the room! We took a taxi from the airport, it was nice to not have to worry about parking." A verified traveller stayed at Historic Inns of Annapolis Posted 2 days ago [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/526c2bf4_y.jpg) ### Hampton Inn Baltimore/Glen Burnie 5/5 Excellent "Rooms were clean and staff was very friendly " A verified traveller stayed at Hampton Inn Baltimore/Glen Burnie Posted 5 days ago [](https://expedia.ca/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) ### Best Western Plus Hotel & Conference Center 5/5 Excellent "Clean room, great location, very friendly and helpful staff" A verified traveller from Currie stayed at Best Western Plus Hotel & Conference Center Posted 5 days ago [](https://expedia.ca/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.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 5/5 Excellent "Fantastic hotel and they upgraded us to a room with a stunning view!" A verified traveller stayed at Annapolis Waterfront Hotel, Autograph Collection Posted 5 days ago [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![Holiday Inn Express White Marsh by IHG](https://images.trvl-media.com/lodging/72000000/71540000/71532200/71532135/7b9d83b4_y.jpg) ### Holiday Inn Express White Marsh by IHG 5/5 Excellent "Hotel is very clean the room was clean and new and very spacious." A verified traveller stayed at Holiday Inn Express White Marsh by IHG Posted 5 days ago [](https://expedia.ca/Baltimore-Hotels-Holiday-Inn-Express-White-Marsh.h71532135.Hotel-Information) ![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 5/5 Excellent "Yes" A verified traveller stayed at Hampton Inn & Suites Edgewood/Aberdeen-South Posted 5 days ago [](https://expedia.ca/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) ### SpringHill Suites Baltimore White Marsh/Middle River 5/5 Excellent "Nothing special, just an uneventful stay." A verified traveller stayed at SpringHill Suites Baltimore White Marsh/Middle River Posted 6 days ago [](https://expedia.ca/Baltimore-Hotels-SpringHill-Suites-Baltimore-White-MarshMiddle-River.h23686806.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 5/5 Excellent "The room was exll" A verified traveller stayed at Hilton Garden Inn Baltimore/White Marsh Posted 7 days ago [](https://expedia.ca/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 5/5 Excellent "Staff was great and so was breakfast " A verified traveller stayed at La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh Posted 8 days ago [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) ## 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](https://www.expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.Hotel-Information), which scores a solid 7.4 in guest reviews. This hotel also provides a inviting space 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](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information), 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.ca/Chestertown-Hotels-Cheap-Hotels.0-0-d7215-tCheapHotels.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 - Lodging - Flights - Packages - Cars - Vacation Rentals - More ways to book - [Hostels in Aberdeen Proving Ground ](https://www.expedia.ca/Aberdeen-Proving-Ground-Hostels.d553248634999428212-aaHostels.Travel-Guide-Accommodation) - [Best Western Hotels in Aberdeen Proving Ground ](https://www.expedia.ca/Aberdeen-Proving-Ground-Hotels-Best-Western.0-0-d553248634999428212--bBestWestern.Travel-Guide-Filter-Hotels) - [Aberdeen Proving Ground Hotels ](https://www.expedia.ca/Aberdeen-Proving-Ground-Hotels.d553248634999428212.Travel-Guide-Hotels) - [Apartments in Betterton ](https://www.expedia.ca/Betterton-Apartments.d3000440429-aaApartments.Travel-Guide-Accommodation) - 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