Title: 5 Stars Hotels in Chestertown, Maryland from CA $336 - Find Cheap Chestertown Hotels With 5 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 # 5 Stars Hotels in Chestertown, Maryland from CA $336 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 5 Star Hotels Tonight [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-01&endDate=2025-10-02&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-02&endDate=2025-10-03&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-03&endDate=2025-10-05&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-10-10&endDate=2025-10-12&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chestertown 5 Star Hotels ![Seasonal outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/a6c44038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/11ca06dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/af277faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pendry Baltimore Fells Point 9.4/10 Exceptional (1000) "A fantastic hotel. Great location, pool, services, food, and rooms. One of our best hotel stays in years." CA $518 CA $666 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.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%2F5Star-Chestertown-Hotels.s50-0-d7215.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Chestertown-Hotels.s50-0-d7215.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Chestertown. ![Annapolis Waterfront Hotel, Autograph Collection](https://images.trvl-media.com/lodging/1000000/10000/5100/5075/2011e31d_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Annapolis Waterfront Hotel, Autograph Collection 80 Compromise St, Annapolis, MD CA $295 CA $336 total Nov 2 - Nov 3 includes taxes & fees 8.8/10 Excellent! (868 reviews) [](https://expedia.ca/Annapolis-Hotels-Annapolis-Waterfront-Hotel.h5075.Hotel-Information) ![The Inn at Chesapeake Bay Beach Club](https://images.trvl-media.com/lodging/13000000/12410000/12402300/12402244/986ce82e_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Inn at Chesapeake Bay Beach Club 180 Pier One Road, Stevensville, MD CA $272 CA $337 total Nov 2 - Nov 3 includes taxes & fees 9.4/10 Exceptional! (420 reviews) [](https://expedia.ca/Annapolis-Hotels-The-Inn-At-Chesapeake-Bay-Beach-Club.h12402244.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=03%2F10%2F2025&endDate=04%2F10%2F2025®ionId=7215&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F10%2F2025&endDate=04%2F10%2F2025®ionId=7215&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F10%2F2025&endDate=04%2F10%2F2025®ionId=7215&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F10%2F2025&endDate=04%2F10%2F2025®ionId=7215&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F10%2F2025&endDate=04%2F10%2F2025®ionId=7215&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F10%2F2025&endDate=04%2F10%2F2025®ionId=7215&star=50&star=50&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=2025-10-16&endDate=2025-10-17&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 ![Sagamore Pendry Baltimore](//images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg) ### Sagamore Pendry Baltimore 10/10 Excellent "Absolutely great stay" [](https://expedia.ca/Baltimore-Hotels-Sagamore-Pendry-Baltimore.h17395897.Hotel-Information) ## Find out more about Chestertown ## Five Star Hotels in Chestertown There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Chestertown so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Chestertown and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Chestertown Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Chestertown The results are in, and Chestertown 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Chestertown! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Chestertown today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Chestertown? > How much you pay for a 5-star hotel in Chestertown depends on things like when you want to go and the length of your stay. A top tip for landing the best deal? Use our pricing filters to compare all of the available options for your selected dates. > > > > - Search for the lowest price per night from CA $336 ### What makes a hotel 5 stars in Chestertown? > Exemplary guest service is the hallmark of every 5-star hotel in Chestertown. From the instant you arrive, staff are at your beck and call, whether arranging customized tours or providing a turn-down service. In addition, hotels have to feature top-rate conveniences to be entitled to a 5-star rating. These can include deluxe baths, a wellness centre, pools, gourmet kitchens and knowledgeable concierge. ### Are there any 5-star all-inclusive resorts in Chestertown? > Find a luxury escape that includes your lodging, meals, drinks and entertainment in Chestertown with our filters. Search for properties rated 5 stars and click on the "All inclusive" filter. Make sure you check what's included in the upfront price. 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