Title: Book the Best OCEANFRONT Hotels in Chestertown, MD from CA $325 - Chestertown Hotels with an Ocean View | 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 Oceanfront Hotels in Chestertown, MD from CA $325 ![](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 Oceanfront Hotels Tonight [Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-19&endDate=2025-10-20&adults=2&amenities=OCEAN_VIEW&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-20&endDate=2025-10-21&adults=2&amenities=OCEAN_VIEW&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=OCEAN_VIEW&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=OCEAN_VIEW&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chestertown Oceanfront Hotels ![Room, 2 Queen Beds, Non Smoking, Balcony](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/af281015.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/6d79f12f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/f68fafe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Annapolis Waterfront Hotel, Autograph Collection Historic District 8.8/10 Excellent (872) "Clean room. Friendly staff awesome location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brent CA $285 CA $325 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.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=2025-11-02&endDate=2025-11-03®ionId=7215&adults=2&room_views_group=ocean_room_view&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Chestertown ### Discover top Chestertown attractions Chestertown, Maryland, offers a charming blend of history, culture, and outdoor activities that will delight any traveller. Start your journey by exploring the historic district, where cobblestone streets are lined with beautifully preserved 18th-century buildings. The Chestertown Tea Party Festival, held annually, commemorates the town's pivotal role in the American Revolution and is a lively celebration with parades, crafts, and local cuisine. For nature enthusiasts, the nearby Sassafras Natural Resources Management Area presents a stunning backdrop for hiking and birdwatching, showcasing the region's diverse ecosystems. Art lovers will appreciate the Chestertown Arts League, which hosts a variety of exhibitions and workshops, providing an insight into local talent. Additionally, a relaxing cruise along the Chester River allows you to soak in the area’s picturesque scenery while learning about its rich maritime history. When it comes to accommodation, consider staying near the waterfront, where boutique hotels offer not only comfort but also stunning views of the river. Imagine enjoying a morning coffee while watching boats glide by, or taking a leisurely stroll along the waterfront, followed by a gourmet meal at a nearby restaurant. Chestertown seamlessly combines a quaint, community spirit with activities, making it a perfect spot for a memorable family getaway. ### Find the best oceanfront hotels and resorts in Chestertown For those seeking a picturesque getaway in Chestertown, Maryland, these hotels offer stunning ocean views and a serene atmosphere, perfect for unwinding by the water. [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 scenic vacations:** The Lodge at Great Oak Landing is an ideal retreat for travelers, an excellent guest review rating of 8.2. With breathtaking marina and water views, guests can indulge in the beauty of the Chesapeake Bay right from their accommodations. The lodge also features direct beach access, ensuring that travelers can easily enjoy sun-soaked days by the water's edge. - **Other amenities:** Guests will appreciate the array of recreational options, including a shared secured pool with sun loungers and a private sandy beach for relaxation. For active travelers, the lodge offers 24-hour fitness facilities, a golf course onsite, and beach volleyball for some friendly competition. Additional conveniences include self-parking, a mini-refrigerator in rooms, and beach umbrellas for those sunny days by the shore. - **Nearby attractions:** Kinnairds Point Drive - 19.6 km, Still Pond Station Park - 24.5 km ## Top Chestertown Hotel Reviews ## Frequently asked questions ### What is Chestertown like for a seaside holiday? > Make your Chestertown getaway exceptional by staying somewhere with coastal views. Take a break from the beach and experience the university life in Chestertown. ### What are the highlights to see in Chestertown? > After checking into your accommodation of choice, you'll probably want to venture out and explore. If you're eager to check out the beaches, head to Betterton Beach or Main Beach for some relaxation by the water. Experience the area's university life, and make time for local attractions like Washington College and River Arts Chestertown. For even more to see and do, pay a visit to Historical Society of Kent County Maryland or Rolphs Wharf Marina. ### Why should I choose an oceanview hotel for my Chestertown vacation? > Reward yourself with an oceanview hotel and enjoy great sea views during your trip to Chestertown. 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