Title: Book the Best BEACH RESORTS in Chestertown, MD from CA $126 - 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) ![](https://mediaim.expedia.com/destination/2/6785bfdbe6f67238f03adb254741e2d9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Assya A # Find beach hotels in Chestertown, MD from CA $126 ![](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 [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-15&endDate=2025-10-16&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-16&endDate=2025-10-17&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chestertown Beach Hotel ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.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) ![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 Chestertown 8.6/10 Excellent (828) "Great service. Very clean." CA $143 CA $159 total includes taxes & fees Oct 19 - Oct 20 [](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) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/799945fa.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) ![1 bedroom, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/8b9992bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn & Suites Chestertown Chestertown 7.2/10 Good (404) "We had a great stay with our two Pups.. The room was very nice and comfortable and very clean." CA $114 CA $126 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Chestertown-Hotels-Red-Roof-Inn-Suites-Chestertown.h40352.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) ![Exterior](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/50bc617c.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) ### Driftwood Inn Chestertown 5.2/10 (174) "Rooms are clean, staf was helpful " [](https://www.expedia.ca/Chestertown-Hotels-Driftwood-Inn.h4862316.Hotel-Information) ![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/97000000/96830000/96826300/96826266/01b06110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed with Sofa bed, Marina View](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/3449c94b.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) ### 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!!" CA $186 CA $212 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/04bd524d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, free WiFi, bed sheets](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/44ce5b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/a4be0d3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/c04c0cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### First Floor Studio Apartment in Historic Chestertown Chestertown 9.6/10 Exceptional (103) "A charming studio in a quiet neighborhood. great directions from host on how to use the property - " CA $139 CA $223 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994126/39c19e25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994126/1680c746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994126/6557d1f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, video library](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994126/37d3c420.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town Chestertown 9.8/10 Exceptional (84) "We had a wonderful weekend. Thank you!" [](https://www.expedia.ca/Chestertown-Hotels-Chester-River-Waterfront.h18994126.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/63000000/62980000/62979100/62979011/fa04023d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/63000000/62980000/62979100/62979011/35abca2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/63000000/62980000/62979100/62979011/11b5c10b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/63000000/62980000/62979100/62979011/344289cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful, spacious waterfront home, an easy walk to historic Chestertown Chestertown 9.8/10 Exceptional (22) "We had a great time" [](https://www.expedia.ca/Chestertown-Hotels-Beautiful.h62979011.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/61000000/60540000/60534400/60534321/bf30133d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/61000000/60540000/60534400/60534321/515ae23d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/61000000/60540000/60534400/60534321/af2d4f46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/61000000/60540000/60534400/60534321/fa6f5596.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock Chestertown 10/10 Exceptional (61) "Great!" [](https://www.expedia.ca/Chestertown-Hotels-350-Acre-Waterfront-Farm-High-Speed-Internet.h60534321.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/55000000/54850000/54841100/54841025/e626cb61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/55000000/54850000/54841100/54841025/1723fbc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/55000000/54850000/54841100/54841025/adbcc20f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/55000000/54850000/54841100/54841025/f72e2547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Country Estate in Historic District Chestertown 10/10 Exceptional (70) "Great hosts, location, gardens, and overallstay! " [](https://www.expedia.ca/Chestertown-Hotels-Country-Estate-In-Historic-District.h54841025.Hotel-Information) ![On the beach, sun loungers](https://images.trvl-media.com/lodging/65000000/65000000/64994000/64993941/31435eda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/65000000/64994000/64993941/3c396535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/65000000/65000000/64994000/64993941/e6a8684a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/65000000/65000000/64994000/64993941/df0f5e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! Chestertown 10/10 Exceptional (83) "One of our favorite spots! Never disappoints." [](https://www.expedia.ca/Chestertown-Hotels-Private-Waterfront-Paradise-W-Pier-Kayak-To-Historic-Chestertown.h64993941.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=2025-10-29&endDate=2025-10-30®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](//images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "Nice hotel" [](https://expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ## Frequently asked questions ### What is Chestertown like for travelers who love the beach? > Known for its university life, Chestertown offers a lot for the traveler planning a getaway. ### What's the best hotel for a beach vacation in Chestertown? > [The Lodge at Great Oak Landing](https://www.expedia.ca/Chestertown-Hotels-The-Lodge-At-Great-Oak-Landing.h96826266.Hotel-Information) is a top lodge with a seasonal outdoor pool and 3 bars/lounges, and it's located near a private beach. ### When's the best time for a beach vacation in Chestertown? > You can plan your beach trip with this snapshot of the seasons in Chestertown: The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches. ### What is there to see and do around Chestertown? > After arriving and checking into your hotel, you'll probably want to explore your surroundings. Beach lovers can head straight to Betterton Beach or Main Beach for some quality time by the water. Experience the area's university life, and make time for local attractions like Washington College and River Arts Chestertown. For more things to see and do, consider visiting Historical Society of Kent County Maryland or Rolphs Wharf Marina. ### What's the best way to get to my beach hotel in Chestertown? > Here's some information to help you get to and around your beach accommodation in Chestertown more easily: To get to Chestertown, book a flight to Baltimore, MD (MTN-Martin State), the closest major airport, which is located 20.3 mi (32.7 km) from the city center. 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