Title: Visit Chestertown: 2026 Travel Guide for Chestertown, New York | Expedia.com [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) # Chestertown, NY ## Travel Guide ![Aerial view of Hudson River in upstate New York, Chestertown, Riparius Bridge. July 12, 2022](https://images.trvl-media.com/place/89045/d8935802-94c8-4419-b7bf-ae82c253406c.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Aerial view of Hudson River in upstate New York, Chestertown, Riparius Bridge. July 12, 2022](https://images.trvl-media.com/place/89045/d8935802-94c8-4419-b7bf-ae82c253406c.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![A winter scene](https://images.trvl-media.com/place/89045/03fff121-2e0b-4e9d-87bf-e8549eff3948.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Chestertown Where to stay Things to do Reviews ### Where to stay in Chestertown ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Chester Shores When in Chester Shores, you can plan a visit to Loon Lake Beach and Loon Lake, some noteworthy sights in the nearby area. [](https://expedia.com/Lake-George-Chester-Shores.dx553248635976471458) [See our Where To Stay guide](https://expedia.com/Chestertown.dx89045.Where-To-Stay?rfrr=TG.LP.Dest.Neighborhoods) - Chestertown Hotel Deals - Vacation Rentals in Chestertown ![The Fern Lodge](https://images.trvl-media.com/lodging/2000000/1540000/1539000/1538972/f2181584_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Fern Lodge 46 Fiddlehead Bay Rd. Chestertown NY $478 nightly $531 total Feb 11 - Feb 12 Total with taxes and fees Book a stay at this beach B&B in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Friends Lake and Loon Lake Beach are located ... 9.8/10 Exceptional! (47 reviews) I cannot say enough good things about the Fern Lodge. Beautiful atmosphere, wonderful host. Will be returning! Reviewed on Dec 27, 2025 [](https://expedia.com/Hotel-Search?startDate=2%2F11%2F2026&endDate=2%2F12%2F2026&selected=1538972&PinnedHotelID=1538972&HadPinnedHotel=true®ionId=89045) ![Eagles Nest at Loon Lake near Gore Mountain](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/73dd065d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Eagles Nest at Loon Lake near Gore Mountain Chestertown NY $680 nightly $755 total Mar 8 - Mar 9 Total with taxes and fees Book a stay at this family-friendly vacation home in Chestertown. Enjoy a garden, laundry facilities, and a pool table. Popular attractions Loon Lake and Loon ... 9.8/10 Exceptional! (111 reviews) Great house. Great location Reviewed on Jan 4, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%2F2026&selected=18956145&PinnedHotelID=18956145&HadPinnedHotel=true®ionId=89045) ![Six Flags Great Escape Lodge & Indoor Waterpark](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/fcd6f5d2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Six Flags Great Escape Lodge & Indoor Waterpark 89 Six Flags Dr Queensbury NY $144 nightly $159 total Mar 8 - Mar 9 Total with taxes and fees Book a stay at this family-friendly resort in Queensbury. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the breakfast and the helpful staff ... 7.8/10 Good! (1,514 reviews) Clean room, food at the restaurant was great Reviewed on Feb 4, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%2F2026&selected=1385446&PinnedHotelID=1385446&HadPinnedHotel=true®ionId=89045) [See all 1,533 properties in Chestertown](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=2%2F11%2F2026&endDate=2%2F12%2F2026®ionId=89045) 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. ![Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George](https://images.trvl-media.com/lodging/77000000/76330000/76320400/76320395/c6d64672_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George Chestertown NY Stay at this apartment in Chestertown. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Friends Lake and Tripp Pond are located ... 9.8/10 Exceptional! (73 reviews) Excellent stocked kitchen, warm fireplace. Spotlessly cleaned. We loved it! Had everything we could have possibly needed. Warm, comfortable, and beautiful scenery. Reviewed on Jan 3, 2026 [](https://expedia.com/Chestertown-Hotels-Unique-Adirondack-Estate-On-Hudson-River-Near-Gore-Mountain-Lake-George.h76320395.Hotel-Information) ![Elizabeth. A Guest House Near Lake George. ](https://images.trvl-media.com/lodging/34000000/33960000/33955800/33955795/8b4efd64_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Elizabeth. A Guest House Near Lake George. Chestertown NY Stay at this vacation home in Chestertown. Enjoy free WiFi, private pools, and a water park. Popular attractions Loon Lake Beach and Friends Lake are located ... 8/10 Very Good! (35 reviews) The house was beautiful and charming and plenty of space. We have no complaints but recommend hand towels in the bathrooms. Probably will look up this place again for a skiing trip this winter. Reviewed on Aug 10, 2025 [](https://expedia.com/Chestertown-Hotels-Elizabeth-A-Guest-House-Near-Lake-George.h33955795.Hotel-Information) ![Eagles Nest at Loon Lake near Gore Mountain](https://images.trvl-media.com/lodging/19000000/18960000/18956200/18956145/73dd065d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Eagles Nest at Loon Lake near Gore Mountain Chestertown NY Book a stay at this family-friendly vacation home in Chestertown. Enjoy a garden, laundry facilities, and a pool table. Popular attractions Loon Lake and Loon ... 9.8/10 Exceptional! (111 reviews) Great house. Great location Reviewed on Jan 4, 2026 [](https://expedia.com/Chestertown-Hotels-Eagles-Nest-At-Loon-Lake-Near-Gore-Mountain.h18956145.Hotel-Information) [See all properties in Chestertown](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=89045&sort=VACATION_RENTAL) 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. ## Check Chestertown hotel availability [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2026-02-10&endDate=2026-02-11)[Feb 10 - Feb 11](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2026-02-10&endDate=2026-02-11) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2026-02-11&endDate=2026-02-12)[Feb 11 - Feb 12](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2026-02-11&endDate=2026-02-12) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026)[Feb 13 - Feb 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2%2F20%2F2026&endDate=2%2F22%2F2026)[Feb 20 - Feb 22](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2%2F20%2F2026&endDate=2%2F22%2F2026) ### Popular places to visit ![Loon Lake](https://images.trvl-media.com/place/553248635976196050/b1196dfe-0b1b-43de-9b4b-94dcffab0606.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Loon Lake Commune with nature and explore the great outdoors at Loon Lake during your travels in Chestertown. While you're in the area, stroll along the lakeside. [](https://expedia.com/Loon-Lake-Lake-George.d553248635976196050.Vacation-Attraction) #### Friends Lake Commune with nature and explore the great outdoors at Friends Lake during your travels in Chestertown. While you're in the area, stroll along the lakeside. [](https://expedia.com/Friends-Lake-Lake-George.d553248635976195601.Vacation-Attraction) #### Loon Lake Beach If a restful vacation is part of your travel plans, Loon Lake Beach might be the perfect place to seek out during your trip to Chestertown. While you're in the area, stroll along the lakeside. [](https://expedia.com/Loon-Lake-Beach-Chestertown.d553248621554184980.Vacation-Attraction) ## Reviews of Chestertown 4.3 Top Destination 5 - Excellent 4 4 - Good 4 3 - Okay 1 2 - Disappointing 0 1 - Terrible 0 ### 5/5 - Excellent Verified traveler Very quiet and relaxing. ### 4/5 - Good Verified traveler Love the hiking. ### 5/5 - Excellent JoeGould We will definitely be coming back in the spring! ### 5/5 - Excellent Batt Adorable village ## Cities near Chestertown ![August 20 2024, Sunny afternoon summer aerial image of the area surrounding Bolton Landing, NY, USA and Lake George.](https://images.trvl-media.com/place/55597/c1cee649-2a4e-4ab8-8a25-4dfebb2ecf85.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Bolton Landing ![Creek and trees in New England in foliage season, panoramic view](https://images.trvl-media.com/place/139117/b981d45f-bb71-4ae4-8e49-4da9e4c0411c.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### North Creek ![GF0Y54 The Upper Hudson River in summer. Warrensburg, NY.](https://images.trvl-media.com/place/171313/56336380-5c2b-4bfc-a7db-e9d033755265.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Warrensburg ![Dramatic Autumn Sunset over Lower Saranac Lake](https://images.trvl-media.com/place/183662/03a29937-6dee-4cf8-8c99-afc74a2252aa.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Diamond Point ## 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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[Car rentals near North Creek ](https://www.expedia.com/Car-Rentals-In-North-Creek.d139117.Car-Rental-Guide) - [Brant Lake Vacation Rentals ](https://www.expedia.com/Brant-Lake-Vacation-Rentals.d6347839.Travel-Guide-VacationRentals) - [Pottersville Vacation Rentals ](https://www.expedia.com/Pottersville-Vacation-Rentals.d6349845.Travel-Guide-VacationRentals) - [Adirondack Vacation Rentals ](https://www.expedia.com/Adirondack-Vacation-Rentals.d6349269.Travel-Guide-VacationRentals) - [North Creek Vacation Rentals ](https://www.expedia.com/North-Creek-Vacation-Rentals.d139117.Travel-Guide-VacationRentals) - Cities near Chestertown - Places of interest [Bolton Landing](https://expedia.com/Bolton-Landing.dx55597)[North Creek](https://expedia.com/North-Creek.dx139117)[Warrensburg](https://expedia.com/Warrensburg.dx171313)[Diamond Point](https://expedia.com/Diamond-Point.dx183662)[Brant Lake](https://expedia.com/Brant-Lake.dx6347839)[Johnsburg](https://expedia.com/Johnsburg.dx6349362)[Pottersville](https://expedia.com/Pottersville.dx6349845)[Wevertown](https://expedia.com/Wevertown.dx3000450116)[Riparius](https://expedia.com/Riparius.dx553248635975950120) - [Loon Lake Beach ](https://expedia.com/Loon-Lake-Beach-Chestertown.d553248621554184980.Vacation-Attraction) - [Gore Mountain Ski Resort ](https://expedia.com/Gore-Mountain-Ski-Resort-North-Creek.d6326108.Vacation-Attraction) - [Lake George ](https://expedia.com/Lake-George-New-York.d642804417676009472.Vacation-Attraction) - [Six Flags Great Escape ](https://expedia.com/Six-Flags-Great-Escape-New-York.d6064469.Vacation-Attraction) - [Million Dollar Beach ](https://expedia.com/Million-Dollar-Beach-New-York.d6247910.Vacation-Attraction) - [Lake George Steamboat Company ](https://expedia.com/Lake-George-Steamboat-Company-Lake-George.d6171515.Vacation-Attraction) - [Fort William Henry Museum ](https://expedia.com/Fort-William-Henry-Museum-Lake-George.d6064463.Vacation-Attraction) - [Outlets at Lake George ](https://expedia.com/Outlets-At-Lake-George-Lake-George.d6210494.Vacation-Attraction) - [Hudson River ](https://expedia.com/Hudson-River-New-York.d681942362185793536.Vacation-Attraction) - 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[Hearthstone Point Campground ](https://expedia.com/Hearthstone-Point-Campground-Lake-George.d553248621579082980.Vacation-Attraction) - [House of Frankenstein Wax Museum ](https://expedia.com/House-Of-Frankenstein-Wax-Museum-Lake-George.d6064461.Vacation-Attraction) - [Lake George Forum ](https://expedia.com/Lake-George-Forum-Lake-George.d6181453.Vacation-Attraction) - [Natural Stone Bridge and Caves ](https://expedia.com/Natural-Stone-Bridge-And-Caves-Pottersville.d6230830.Vacation-Attraction) - [French Mountain Commons ](https://expedia.com/French-Mountain-Commons-Lake-George.d6210994.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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