Title: The Best 4 Star Hotels in Chestertown, NY from $181 | Expedia.com [Chestertown Travel Guide](https://expedia.com/Chestertown.dx89045)[Hotels in Chestertown](https://expedia.com/Chestertown-Hotels.d89045.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.com/Chestertown-Vacation-Rentals.d89045.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.com/Cheap-Flights-To-Chestertown.d89045.Travel-Guide-Flights)[Car Rentals in Chestertown](https://expedia.com/Car-Rentals-In-Chestertown.d89045.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.com/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__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/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 4 Star Hotels Tonight [Mar 23 - Mar 24](https://www.expedia.com/Hotel-Search?regionId=89045&startDate=2026-03-23&endDate=2026-03-24&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 24 - Mar 25](https://www.expedia.com/Hotel-Search?regionId=89045&startDate=2026-03-24&endDate=2026-03-25&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=89045&startDate=2026-03-27&endDate=2026-03-29&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=89045&startDate=2026-04-03&endDate=2026-04-05&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chestertown 4-star hotels ![Indoor/outdoor pool](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320727/e5159e2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320727/77f4594f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320727/d8734040.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, coffee/tea maker, cleaning supplies, paper towels](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320727/b8213718.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lodges At Cresthaven [](https://www.expedia.com/Lake-George-Hotels-Lodges-At-Cresthaven.h1320727.Hotel-Information) Lake George 9.4/10 Exceptional (569 reviews) "Beautiful and in pristine condition." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle $163 nightly $181 total Mar 24 - Mar 25 Total with taxes and fees [](https://www.expedia.com/Lake-George-Hotels-Lodges-At-Cresthaven.h1320727.Hotel-Information) ![Premier Room | 1 bedroom, premium bedding, individually decorated](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/65af6a05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/541a0034.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) ![Premier Room | 1 bedroom, premium bedding, individually decorated](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/3d1666a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Friends Lake Inn [](https://www.expedia.com/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 $223 nightly $248 total Mar 24 - Mar 25 Total with taxes and fees [](https://www.expedia.com/Lake-George-Hotels-Friends-Lake-Inn.h9675030.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) ![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19370000/19366100/19366003/c83090ec.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) ![Boating](https://images.trvl-media.com/lodging/20000000/19370000/19366100/19366003/81214daf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chateau Rooms [](https://www.expedia.com/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.com/Lake-George-Hotels-Chateau-Rooms.h19366003.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.com/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.com/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.com/Hotel-Search?startDate=2026-04-06&endDate=2026-04-07&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 The preparation of any vacation starts with picking a spot. Chestertown has been a popular choice with guests because of everything it offers. However, "location, location, location" applies to more than just your vacation destination. When you want a vacation that is incredible from beginning to end, you need the right hotel. ### Accommodations as Scenic as the City Chestertown saw its fair share of visitors this past year. Our comment section features reviews that highlight how incredible these accommodations are. The resorts found here aim to make your stay as gratifying as your nights exploring Chestertown. You won't need to go far for a delicious breakfast, an invigorating spa treatment, or to keep up with your exercise schedule during your stay, thanks to all that these hotels provide. They strive to make the facilities and grounds hospitable from the time you step onto the property and with every step throughout the hotel. Rooms have been configured to keep your utmost comfort in mind, with amenities like in-room tea or coffee, designer bathroom products, and ultra-comfortable bedding. So, lay back and unwind. Moreover, if you find yourself in need of something more, you can rest easy the staff will do their best to ensure you continue to be happy during your stay. These hotels are so nice that you'll regret the day you have to return home. ### Book a 4-Star Hotel in Chestertown Today! Your trip to Chestertown should be one that you'll recollect for years to come, and booking a 4-star hotel can help create memories that are fantastic. With Expedia, you will get great prices on world-class accommodations to take your trip to the next level. ## 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 $181 ### 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 Rentals - [Hotels near Loon Lake Beach ](https://www.expedia.com/Loon-Lake-Beach-Hotels.0-l553248621554184980-0.Travel-Guide-Filter-Hotels) - [Brant Lake Hotels ](https://www.expedia.com/Brant-Lake-Hotels.d6347839.Travel-Guide-Hotels) - [Cabin Rentals in Brant Lake ](https://www.expedia.com/Brant-Lake-Cabins.d6347839-aaCabins.Travel-Guide-Accommodation) - [Resorts in Brant Lake ](https://www.expedia.com/Brant-Lake-Resorts.d6347839-aaResorts.Travel-Guide-Accommodation) - [B&B in Brant Lake ](https://www.expedia.com/Brant-Lake-Bed-And-Breakfast.d6347839-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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