Title: 4 Stars Hotels in Chestertown, New York from CA $270 - 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) ![](https://mediaim.expedia.com/destination/2/db61c46cb1c1e36f625f3b3e306714b5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Julie Miller # 4 Stars Hotels in Chestertown, New York from CA $270 ![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 4 Star Hotels Tonight [Sep 28 - Sep 29](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-09-28&endDate=2025-09-29&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 29 - Sep 30](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-09-29&endDate=2025-09-30&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-03&endDate=2025-10-05&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=89045&startDate=2025-10-10&endDate=2025-10-12&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Chestertown 4 Star Hotels ![Exterior](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320727/4993b753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320727/b8213718.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320727/7f753327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1330000/1320800/1320727/1d7dc909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lodges At Cresthaven Lake George 9.4/10 Exceptional (501) "Great place to stay!" CA $243 CA $270 total includes taxes & fees Oct 13 - Oct 14 [](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/20000000/19370000/19366100/19366003/6635abb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chateau Rooms Bolton Landing 9.2/10 Wonderful (62) "Had a great experience and will certainly re-visit " [](https://www.expedia.ca/Lake-George-Hotels-Chateau-Rooms.h19366003.Hotel-Information) ![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/8bdcc127.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/65af6a05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/3a2c4196.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/1b13c3a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Friends Lake Inn Chestertown 8.8/10 Excellent (101) "Staff was great. The inn is unique. Perfect!" CA $311 CA $345 total includes taxes & fees Sep 29 - Sep 30 [](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=2025-10-12&endDate=2025-10-13&adults=2®ionId=89045) ![](https://mediaim.expedia.com/destination/2/db61c46cb1c1e36f625f3b3e306714b5.jpg?impolicy=fcrop&w=900&h=736&p=1&q=high) Photo by Julie Miller ## Top Chestertown Hotel Reviews ![Friends Lake Inn](//images.trvl-media.com/lodging/10000000/9680000/9675100/9675030/8bdcc127_y.jpg) ### Friends Lake Inn 10/10 Excellent "Staff was great. The inn is unique. Perfect!" [](https://expedia.ca/Lake-George-Hotels-Friends-Lake-Inn.h9675030.Hotel-Information) ## 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? > Relax in comfort at [Friends Lake Inn](https://www.expedia.ca/Lake-George-Hotels-Friends-Lake-Inn.h9675030.Hotel-Information). According to reviews by our guests, this is one of Chestertown's top 4-star hotels. ### How much does it cost to stay in a 4-star hotel in Chestertown? > To book a 4-star hotel in Chestertown that matches your budget, use Expedia's filters. Check out the availability during your travel dates and use our pricing filter to set your limit. You can also list your results by the most economical retreat first. > > > > - Search for the lowest price from CA $270 ### What's the difference between 5-star and 4-star hotels in Chestertown? > Treat yourself to luxury living during your Chestertown getaway by staying at a 4-star hotel. As well as featuring upmarket accommodations, these properties are typically filled with amenities such as large beds, bathrobes and plenty more. A 5-star hotel will go above and beyond to make your trip an even more lavish and unforgettable one. 24-hour front desk, elegant furnishings and gourmet dining are just the start of the first-rate services and conveniences you'll likely get access to. ## 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) - [3 Star Hotels in Great Sacandaga Lake Area](https://www.expedia.ca/3Star-Great-Sacandaga-Lake-Area-Hotels.s30-0-d6055963.Travel-Guide-Filter-Hotels) - 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