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) ![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 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 [26 Nov - 27 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2025-11-26&endDate=2025-11-27&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) Tomorrow [27 Nov - 28 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2025-11-27&endDate=2025-11-28&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) This weekend [28 Nov - 30 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) Next weekend [5 Dec - 7 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=7215&startDate=2025-12-05&endDate=2025-12-07&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) ## 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) ![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) ![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) ### Comfort Inn & Suites Chestertown Chestertown 8.6/10 Excellent (855) "The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Santa £86 includes taxes & fees 30 Nov - 1 Dec [](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 (417) "This property was clean but dated. The carpet was stained, the furniture and fixtures were worn and broken, towels were washed but old and in need of replacement." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Derek £61 includes taxes & fees 3 Dec - 4 Dec [](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) ![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 Chestertown 5.2/10 (175) "Rooms are clean, staf was helpful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daryl £54 includes taxes & fees 24 Dec - 25 Dec [](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/97000000/96830000/96826300/96826266/72a73d25.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) ![Point of interest](https://images.trvl-media.com/lodging/97000000/96830000/96826300/96826266/01b06110.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Lodge at Great Oak Landing Chestertown 8.0/10 Very good (76) "Very nice rooms, " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephania £86 includes taxes & fees 30 Nov - 1 Dec [](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) ![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) ![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 (106) "Amazing and neat and very private " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexander M. £124 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Chestertown-Hotels-First-Floor-Studio-Apartment-In-Historic-Chestertown.h75854900.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) ![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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shaama P. [](https://www.expedia.co.uk/Chestertown-Hotels-350-Acre-Waterfront-Farm-High-Speed-Internet.h60534321.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/63000000/62980000/62979100/62979011/11574354.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) ### Beautiful, spacious waterfront home, an easy walk to historic Chestertown Chestertown 9.8/10 Exceptional (23) "We had a great time" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Harold L. [](https://www.expedia.co.uk/Chestertown-Hotels-Beautiful.h62979011.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) ![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) ![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 (85) "Everything we needed was there. Owners next sore are super nice and hrphful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) steven s. [](https://www.expedia.co.uk/Chestertown-Hotels-Chester-River-Waterfront.h18994126.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/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) ![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! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robin G. [](https://www.expedia.co.uk/Chestertown-Hotels-Country-Estate-In-Historic-District.h54841025.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34300000/34299400/34299392/a71316a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/35000000/34300000/34299400/34299392/320297b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34300000/34299400/34299392/ab8bf6bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34300000/34299400/34299392/3babab79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Contemporary waterfront house with private dock & kayaks! Chestertown 10/10 Exceptional (66) "It was super peaceful and relaxing. We fished and read and spent the week decompressing and absolutely loved the area!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roni L. [](https://www.expedia.co.uk/Chestertown-Hotels-Contemporary-Waterfront-House-With-Private-Dock-Kayaks.h34299392.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=2025-12-10&endDate=2025-12-11®ionId=7215&adults=2&travelerType=beach&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_FR-DE-MX-UK_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Save up to 40% on select hotels. [Book now](https://expedia.co.uk/cheap-deals?rfrr=AFFINITY_BF_PROMO_7215) ## 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](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "N/A" [](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 Earle Landing for some quality time by the water. Experience the area's university life, and make time for local attractions such as Washington College and Historical Society of Kent County Maryland. For more things to see and do, consider visiting Chestertown Historic District 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. If you'd like to venture out around the area, you may want to rent a car for your trip. ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - More ways to book - [Cheap Hotels in Aberdeen](https://www.expedia.co.uk/Aberdeen-Hotels-Budget-Hotels.0-0-d6044-tBudgetHotels.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Aberdeen](https://www.expedia.co.uk/Aberdeen-Hotels-Gay-Friendly-Hotel.0-0-d6044-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Aberdeen](https://www.expedia.co.uk/Aberdeen-Hotels-Hotel-With-Early-Check-In.0-0-d6044-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Hotels with Entertainment in Aberdeen](https://www.expedia.co.uk/Aberdeen-Hotels-Hotel-With-Entertainment.0-0-d6044-thotelwithentertainment.Travel-Guide-Filter-Hotels) - [Hotels with Indoor Pools in Aberdeen](https://www.expedia.co.uk/Aberdeen-Hotels-Hotels-With-Indoor-Pools.0-0-d6044-tHotelswithIndoorPools.Travel-Guide-Filter-Hotels) - 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