Title: TOP Chestertown Beach Resorts for 2025 - Hotels on the Beach in Chestertown, MD | Expedia.co.uk [Chestertown Travel Guide](https://expedia.co.uk/Chestertown.dx7215)[Hotels in Chestertown](https://expedia.co.uk/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[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) ![](https://mediaim.expedia.com/destination/2/6785bfdbe6f67238f03adb254741e2d9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Assya A # Find Beach Resorts in Chestertown, MD ![](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 ## Check availability on Chestertown Beach Resorts & Hotels Tonight [12 Oct - 13 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2025-10-12&endDate=2025-10-13&adults=2&amenities=BEACH&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&amenities=BEACH&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&amenities=BEACH&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&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chestertown Beach Resorts & Hotels ![Lobby](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46.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) ![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) ### 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) ![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) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/50000/40400/40352/799945fa.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/1af5cb1b.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) ![TV](https://images.trvl-media.com/lodging/5000000/4870000/4862400/4862316/5800905c.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.co.uk/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 | 1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/3449c94b.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/b3c72334.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) ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/04bd524d.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) ![Interior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/a4be0d3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/92366292.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 - " £122 includes taxes & fees 13 Oct - 14 Oct [](https://www.expedia.co.uk/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) ![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) ![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) ![Smart TV, fireplace, DVD player, video library](https://images.trvl-media.com/lodging/19000000/19000000/18994200/18994126/4b182ec5.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.co.uk/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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/63000000/62980000/62979100/62979011/35abca2f.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.co.uk/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) ![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) ![4 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/61000000/60540000/60534400/60534321/93888d05.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.co.uk/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) ![Exterior detail](https://images.trvl-media.com/lodging/55000000/54850000/54841100/54841025/f72e2547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/55000000/54850000/54841100/54841025/cffe9d0c.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) ### Country Estate in Historic District Chestertown 10/10 Exceptional (70) "Great hosts, location, gardens, and overallstay! " [](https://www.expedia.co.uk/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) ![Dining](https://images.trvl-media.com/lodging/65000000/65000000/64994000/64993941/8a9eaa37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table football, books](https://images.trvl-media.com/lodging/65000000/65000000/64994000/64993941/df0f5e5a.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) ### Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! Chestertown 10/10 Exceptional (82) "One of our favorite spots! Never disappoints." [](https://www.expedia.co.uk/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.co.uk/Hotel-Search?startDate=2025-10-26&endDate=2025-10-27®ionId=7215&adults=2&travelerType=beach&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Chestertown ### Chestertown and its attractions for beach lovers Chestertown, Maryland, beautifully located along the Chester River, offers a delightful blend of historical charm and natural beauty, perfect for beach-loving travellers. Begin your adventure at Wilmer Park, where sandy shores meet lush green spaces; it's an excellent spot for a family picnic or a leisurely walk along the waterfront, with beautiful views of the river. Just a short drive away, you can explore the serene, sandy stretches of Sandy Point State Park, where swimming, sunbathing, and beachcombing await. For a unique experience, head to the nearby Eastern Neck National Wildlife Refuge, where you can enjoy quiet walks alongside tidal marshes while spotting diverse bird species. If you're keen on sailing or kayaking, Chestertown’s local marinas provide rentals and guided tours, giving you an adventurous way to explore the waterways. When it comes to accommodation, consider staying at one of the charming inns or boutique hotels in the heart of Chestertown, where attentive service and comfortable amenities ensure a relaxing retreat after a day of exploration. The historic district's cobblestone streets are perfect for evening strolls, with local eateries offering fresh seafood and regional delicacies, making your stay not just memorable but a true taste of Maryland's coastal culture. ## 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.co.uk/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ## Frequently asked questions ### What is Chestertown like for travellers who love the beach? > Known for its university life, Chestertown offers a lot for the traveller planning a getaway. ### What's the best place to stay for a beach holiday in Chestertown? > [The Lodge at Great Oak Landing](https://www.expedia.co.uk/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 holiday in Chestertown? > You can plan your beach trip with this snapshot of year-round temperatures in Chestertown: The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm. ### 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 such as 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 centre. 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