Title: 4 Stars Hotels in Chestertown, New York from CA $210 - Find Cheap Chestertown Hotels With 4 Stars | Expedia.ca [Chestertown Travel Guide](https://expedia.ca/Chestertown.dx89045)[Hotels in Chestertown](https://expedia.ca/Chestertown-Hotels.d89045.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.ca/Chestertown-Vacation-Rentals.d89045.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.ca/Cheap-Flights-To-Chestertown.d89045.Travel-Guide-Flights)[Chestertown Car Rentals](https://expedia.ca/Car-Rentals-In-Chestertown.d89045.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.ca/Chestertown.d89045.Destination-Travel-Guides) ![A winter scene](https://images.trvl-media.com/place/89045/03fff121-2e0b-4e9d-87bf-e8549eff3948.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Julie Miller ![](https://images.trvl-media.com/place/89045/03fff121-2e0b-4e9d-87bf-e8549eff3948.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Jan 13 - Jan 14](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-01-13&endDate=2026-01-14&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 14 - Jan 15](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-01-14&endDate=2026-01-15&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-01-16&endDate=2026-01-18&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2026-01-23&endDate=2026-01-25&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestertown 4-star hotels ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320727/7f753327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320727/2d8dd799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320727/b0ba53a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320727/1f0c1d2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lodges At Cresthaven [](https://www.expedia.ca/Lake-George-Hotels-Lodges-At-Cresthaven.h1320727.Hotel-Information) Lake George 9.4/10 Exceptional (549 reviews) "It was a pleasant stay, very little staff attention" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pablo Andres CA $189 CA $210 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Lake-George-Hotels-Lodges-At-Cresthaven.h1320727.Hotel-Information) ![Luxury Studio Suite, 1 King Bed, Lake View (#1) | Lake view](https://images.trvl-media.com/lodging/20000000/19370000/19366100/19366003/5eccbeb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/20000000/19370000/19366100/19366003/81214daf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/20000000/19370000/19366100/19366003/8b5fd1af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19370000/19366100/19366003/c83090ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chateau Rooms [](https://www.expedia.ca/Lake-George-Hotels-Chateau-Rooms.h19366003.Hotel-Information) Bolton Landing 9.2/10 Wonderful (66 reviews) "Such a beautiful time, So clean, and cozy. Such a beautiful, peaceful, and romantic place. Very enchanting, and the owner is so kind, and caring. Def cant wait to go back again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cindy [](https://www.expedia.ca/Lake-George-Hotels-Chateau-Rooms.h19366003.Hotel-Information) ![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/65af6a05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/bf13d00a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/3d1666a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room | Television](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/0d6c5cd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Friends Lake Inn [](https://www.expedia.ca/Lake-George-Hotels-Friends-Lake-Inn.h9675030.Hotel-Information) Chestertown 8.6/10 Excellent (102 reviews) "Friendly staff, room was clean, well maintained. Ate at the restaurant, food was great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin [](https://www.expedia.ca/Lake-George-Hotels-Friends-Lake-Inn.h9675030.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-d89045.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-d89045.Travel-Guide-Filter-Hotels) ## Learn more about Chestertown Nestled in the Adirondacks, this charming town offers hiking trails and kayaking on Friends Lake during summer months. Winter visitors can hit the slopes at nearby Gore Mountain in North Creek or explore the Natural Stone Bridge and Caves in Pottersville. [See all hotels in Chestertown](https://www.expedia.ca/Hotel-Search?startDate=2026-01-27&endDate=2026-01-28&adults=2®ionId=89045) ![A winter scene](https://images.trvl-media.com/place/89045/03fff121-2e0b-4e9d-87bf-e8549eff3948.jpg?impolicy=fcrop&w=900&h=736&p=1&q=high) Photo by Julie Miller ## 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, New York, 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 ### What are the best 4-star hotels in Chestertown? ### How much does it cost to stay in a 4-star hotel in Chestertown? > - Search for the lowest price from CA $210 ### What's the difference between 5-star and 4-star hotels in Chestertown? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [2 Star Hotels in Middleburgh ](https://www.expedia.ca/2Star-Middleburgh-Hotels.s20-0-d6344005.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Plattsburgh ](https://www.expedia.ca/2Star-Plattsburgh-Hotels.s20-0-d2816.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Big Moose ](https://www.expedia.ca/3Star-Big-Moose-Hotels.s30-0-d3000008617.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Cooperstown - Otsego Lake ](https://www.expedia.ca/3Star-Cooperstown-Otsego-Lake-Hotels.s30-0-d6055757.Travel-Guide-Filter-Hotels) - 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