Title: 4 Stars Hotels in Chestertown, Maryland from CA $325 - Find Cheap Chestertown Hotels With 4 Stars | Expedia.ca [Chestertown Travel Guide](https://expedia.ca/Chestertown.dx7215)[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 # 4 Stars Hotels in Chestertown, Maryland 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 4 Star Hotels Tonight [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-16&endDate=2025-10-17&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-17&endDate=2025-10-18&adults=2&star=40&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&star=40&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&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chestertown 4 Star 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) ![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) ![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) ### Annapolis Waterfront Hotel, Autograph Collection Historic District 8.8/10 Excellent (871) "Clean room. Friendly staff awesome location. " CA $285 CA $325 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.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) ![Exterior](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/cca95561.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) ### The Inn at Chesapeake Bay Beach Club Stevensville 9.4/10 Exceptional (422) "Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. " CA $272 CA $338 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Chestertown-Hotels.s40-0-d7215.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Chestertown-Hotels.s40-0-d7215.Travel-Guide-Filter-Hotels) ## Explore similar 5-star hotels Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Chestertown. ![Sagamore Pendry Baltimore](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sagamore Pendry Baltimore 1715 Thames St., Baltimore, MD CA $500 CA $645 total Nov 6 - Nov 7 includes taxes & fees 9.2/10 Wonderful! (1,004 reviews) [](https://expedia.ca/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information) Still don't see what you're looking for? [See all properties in Chestertown.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F10%2F2025&endDate=18%2F10%2F2025®ionId=7215&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F10%2F2025&endDate=18%2F10%2F2025®ionId=7215&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F10%2F2025&endDate=18%2F10%2F2025®ionId=7215&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F10%2F2025&endDate=18%2F10%2F2025®ionId=7215&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F10%2F2025&endDate=18%2F10%2F2025®ionId=7215&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=17%2F10%2F2025&endDate=18%2F10%2F2025®ionId=7215&star=40&star=40&amenities=WATER_PARK) 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. ## Learn more about Chestertown Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour. [See all hotels in Chestertown](https://www.expedia.ca/Hotel-Search?startDate=2025-10-30&endDate=2025-10-31&adults=2®ionId=7215) ![](https://mediaim.expedia.com/destination/2/6785bfdbe6f67238f03adb254741e2d9.jpg?impolicy=fcrop&w=400&h=400&p=1&q=high) Photo by Assya A ## Top Chestertown Hotel Reviews ## Find out more about Chestertown If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Chestertown are calling your name. Known for providing first-rate service in amazing locations, each of the Chestertown 4 Stars hotels lets discerning travelers bask in an unforgettable experience. Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day. It’s all waiting for you at the top four star hotels in Chestertown. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Chestertown, Maryland, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Chestertown hotels with 4 Stars provide everything you need to unwind in style. ## Frequently asked questions ### How much does it cost to stay in a 4-star hotel in Chestertown? > To lock in a 4-star hotel in Chestertown that's within your budget, make use of Expedia's sort and search filters. Browse the available options during your preferred dates and use our pricing filter to set your limit. You can also list your results by the cheapest property first. > > > > - Search for the lowest price from CA $645 ### What's the difference between 5-star and 4-star hotels in Chestertown? > Offering a friendly traveller experience and upmarket décor, 4-star hotels are a great option for your Chestertown break. These kinds of accommodations generally come with loads of useful amenities that make it simple to unpack and recharge — think large beds, bathrobes, restaurants and gyms. Or enjoy even more lavishness at a 5-star hotel designed to indulge you in luxury perks and amenities. Concierge assistance, oversized bathrooms and fine dining are typically featured at these deluxe properties. ### Does Chestertown have any 4-star all-inclusive resorts? > Use our "All inclusive" filter to find your dream resort in Chestertown where just about everything is taken care of, from your meals to your room, entertainment and activities. 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