Title: Book the Best BEACH RESORTS in Chestertown, MD from CA $92 - Chestertown Hotels on the Beach| Expedia.ca [Hotels in Chestertown](https://expedia.ca/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[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) ![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find beach hotels in Chestertown, MD from CA $92 - ![](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 ## Check availability on Chestertown Beach Hotel Tonight [Jan 5 - Jan 6](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-05&endDate=2026-01-06&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) Tomorrow [Jan 6 - Jan 7](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-06&endDate=2026-01-07&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) This weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-09&endDate=2026-01-11&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) Next weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-16&endDate=2026-01-18&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) ## Our top choices for Chestertown beach hotels ![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) ![Exterior](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/63592edd.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) ### 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 (1022) "Decent place not loud quiet and out of the way." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tarrell CA $82 CA $92 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/6adbaac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/a8370cf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/a5912d87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/50000/40500/40450/9d10475b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Aberdeen-APG [](https://www.expedia.ca/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.Hotel-Information) Aberdeen 9.0/10 Wonderful (1005) "Room was great and staff excellent. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $117 CA $131 total includes taxes & fees Jan 10 - Jan 11 [](https://www.expedia.ca/Aberdeen-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Aberdeen-APG.h40450.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) ![Reception](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/05b80e5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Hampton Inn & Suites Edgewood/Aberdeen-South [](https://www.expedia.ca/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.Hotel-Information) Edgewood 9.4/10 Exceptional (1016) "Great stay as always" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda CA $111 CA $125 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/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) ![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) ![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 [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) Stevensville 9.2/10 Wonderful (130) "Beautiful and peaceful property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jerry CA $176 CA $243 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Annapolis-Hotels-The-Waterfront-Historic-Kent-Manor-Inn.h194102.Hotel-Information) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/290000/281700/281612/742476e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/290000/281700/281612/256d3c46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/290000/281700/281612/75e8b664.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/290000/281700/281612/d24d6107.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG [](https://www.expedia.ca/Edgewood-Hotels-Holiday-Inn-Express-Edgewood-Aberdeen-Bel-Air.h281612.Hotel-Information) Edgewood 9.0/10 Wonderful (563) "A solid place to stay in the area!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donald CA $118 CA $132 total includes taxes & fees Jan 9 - Jan 10 [](https://www.expedia.ca/Edgewood-Hotels-Holiday-Inn-Express-Edgewood-Aberdeen-Bel-Air.h281612.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/1c3a6583.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/96c882ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/e8c3ab14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/900000/891500/891451/b5f07127.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD [](https://www.expedia.ca/Bel-Air-Hotels-Country-Inn-Suites-By-Radisson.h891451.Hotel-Information) Bel Air 8.8/10 Excellent (1004) "We found the overall hotel and surrounding area very nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacquelyn CA $109 CA $122 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Bel-Air-Hotels-Country-Inn-Suites-By-Radisson.h891451.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/48ed0abe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, dishwasher, cookware/dishes/utensils](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/w3837h2556x3y3-eb803e07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/ae4c61bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/7000000/6710000/6708100/6708043/7074520f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Baltimore / Aberdeen, MD [](https://www.expedia.ca/Aberdeen-Hotels-Home2-Suites-By-Hilton-BaltimoreAberdeen.h6708043.Hotel-Information) Aberdeen 8.8/10 Excellent (340) "Clean room, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie CA $123 CA $137 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Aberdeen-Hotels-Home2-Suites-By-Hilton-BaltimoreAberdeen.h6708043.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/da90f3f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/d2d73c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/04e5ff1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/3000000/2360000/2355900/2355869/190ef686.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites Aberdeen-Bel Air by IHG [](https://www.expedia.ca/Bel-Air-Hotels-Candlewood-Suites-Aberdeen-Edgewood-Bel-Air.h2355869.Hotel-Information) Bel Air 8.0/10 Very good (477) "The staff is great, roon clean & spacious" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $114 CA $128 total includes taxes & fees Jan 7 - Jan 8 [](https://www.expedia.ca/Bel-Air-Hotels-Candlewood-Suites-Aberdeen-Edgewood-Bel-Air.h2355869.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/a4c59418.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/1f3f9838.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/71bdd057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/66000000/65330000/65328000/65327947/96859422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Bel Air [](https://www.expedia.ca/Bel-Air-Hotels-Hilton-Garden-Inn-Bel-Air.h65327947.Hotel-Information) Bel Air 9.2/10 Wonderful (235) "Kind staff, very clean. Lovely stay!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Michelle CA $134 CA $150 total includes taxes & fees Jan 23 - Jan 24 [](https://www.expedia.ca/Bel-Air-Hotels-Hilton-Garden-Inn-Bel-Air.h65327947.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/9f06834f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/b42a3a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/cca95561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Chesapeake Bay Beach Club [](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) Stevensville 9.4/10 Exceptional (433) "Very nice and clean! Only complaints A few stains on the couch And no body lotion. We really enjoyed our stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DEANNA CA $214 CA $273 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.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=2026-01-19&endDate=2026-01-20®ionId=7215&adults=2&travelerType=beach&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Chestertown ### Chestertown and its attractions for beach lovers Located just a short drive from the serene beaches of the Chesapeake Bay, Chestertown, Maryland, offers a delightful blend of charm and coastal adventure for families seeking quality experiences. Start your exploration at Wilmer Park, where the scenic waterfront beckons with picnic spots and walking trails, perfect for a leisurely afternoon with the family. Just a stone’s throw away, the Chestertown Marina invites visitors to enjoy kayaking or paddleboarding, providing a unique perspective of the town from the water. Art enthusiasts can visit the nearby Kent County Arts Council, which showcases local talents and often hosts family-friendly workshops. For a taste of local history, the Custom House Museum offers engaging exhibits that delve into the town's rich maritime heritage. After a day of exploration, families can unwind at hotels along the waterfront, where attentive service and comfortable accommodations ensure a relaxing stay. Opt for a hotel with easy access to the beach, allowing for spontaneous beach outings, while also enjoying the quaint atmosphere of Chestertown’s historic streets, lined with boutique shops and delightful eateries. ### Find the best beach hotels and resorts in Chestertown For those seeking a beach getaway in Chestertown, Maryland, these hotels offer the perfect blend of comfort and coastal charm. Enjoy sun-soaked days and stunning views at these delightful properties. [**The Lodge at Great Oak Landing**](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) - **Why it's great for the ultimate beach vacation spot:** The Lodge at Great Oak Landing is an ideal retreat for beach lovers, a solid guest review rating of 8.2\. Guests can enjoy direct access to a private sand beach, perfect for sunbathing and relaxation. With a variety of beach amenities including sun loungers, a waterfront location, and volleyball courts, it promises a fun-filled coastal experience. - **Other amenities:** This hotel features a shared pool with sun loungers and umbrellas, ensuring ample relaxation options. Active guests can take advantage of the 24-hour fitness facilities, while families will appreciate the playground. Additional conveniences include self-parking options, a mini-refrigerator in rooms, and stunning marina views to enjoy during your stay. - **Nearby attractions:** Kinnairds Point Drive - 19.6 km, Still Pond Station Park - 24.5 km ## Top Chestertown Hotel Reviews ![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "Very nice" [](https://expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ## Frequently asked questions ### What is Chestertown like for travelers who love the beach? ### What's the best hotel for a beach vacation in Chestertown? ### When's the best time for a beach vacation in Chestertown? ### What is there to see and do around Chestertown? ### What's the best way to get to my beach hotel in Chestertown? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Honeymoon Resorts and in Baltimore ](https://www.expedia.ca/Baltimore-Hotels-Honeymoon-Hotels.0-0-d178235-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - 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