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 $425 nightly $472 total Feb 9 - Feb 10 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%2F9%2F2026&endDate=2%2F10%2F2026&selected=1538972&PinnedHotelID=1538972&HadPinnedHotel=true®ionId=89045) ![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 [Get rates](https://expedia.com/Hotel-Search?startDate=2%2F21%2F2026&endDate=2%2F22%2F2026&selected=33955795&PinnedHotelID=33955795&HadPinnedHotel=true®ionId=89045) [](https://expedia.com/Hotel-Search?startDate=2%2F21%2F2026&endDate=2%2F22%2F2026&selected=33955795&PinnedHotelID=33955795&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) [See all 1,533 properties in Chestertown](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=2%2F8%2F2026&endDate=2%2F9%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. ![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) ![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) ![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=2026-02-07&endDate=2026-02-08)[Feb 7 - Feb 8](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2026-02-07&endDate=2026-02-08) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2026-02-08&endDate=2026-02-09)[Feb 8 - Feb 9](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2026-02-08&endDate=2026-02-09) [Next 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) ### 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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[Visit North Creek ](https://www.expedia.com/North-Creek.dx139117) - [Visit Bolton Landing ](https://www.expedia.com/Bolton-Landing.dx55597) - [Tannery Pond Community Center ](https://www.expedia.com/Tannery-Pond-Community-Center-North-Creek.d553248621532665407.Vacation-Attraction) - [North Creek Vacations ](https://www.expedia.com/North-Creek.d139117.Destination-Travel-Guides) - [Car rentals near Brant Lake ](https://www.expedia.com/Car-Rentals-In-Brant-Lake.d6347839.Car-Rental-Guide) - [Car rentals near Pottersville ](https://www.expedia.com/Car-Rentals-In-Pottersville.d6349845.Car-Rental-Guide) - [Car rentals near Wevertown ](https://www.expedia.com/Car-Rentals-In-Wevertown.d3000450116.Car-Rental-Guide) - [Car rentals near Blue Line Outdoor Center ](https://www.expedia.com/Car-Rentals-In-Blue-Line-Outdoor-Center.d553248621532665412.Car-Rental-Guide) - [Car rentals near Adirondack ](https://www.expedia.com/Car-Rentals-In-Adirondack.d6349269.Car-Rental-Guide) - [Car rentals near Up Yonda Farm Environmental Education Center ](https://www.expedia.com/Car-Rentals-In-Up-Yonda-Farm-Environmental-Education-Center.d553248621532665355.Car-Rental-Guide) - [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)[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) - [West Mountain Ski Resort ](https://expedia.com/West-Mountain-Ski-Resort-Queensbury.d6171711.Vacation-Attraction) - [Hudson River ](https://expedia.com/Hudson-River-New-York.d681942362185793536.Vacation-Attraction) - [Shepard's Beach Park ](https://expedia.com/Shepards-Beach-Park-Lake-George.d553248621554160470.Vacation-Attraction) - [Lake George Dog Beach ](https://expedia.com/Lake-George-Dog-Beach-New-York.d6064457.Vacation-Attraction) - [The Sagamore Golf Club ](https://expedia.com/The-Sagamore-Golf-Club-Bolton-Landing.d828201277410185216.Vacation-Attraction) - [Adirondack Winery ](https://expedia.com/Adirondack-Winery-Lake-George.d6217555.Vacation-Attraction) - [Lake George Shoreline Cruises ](https://expedia.com/Lake-George-Shoreline-Cruises-Lake-George.d6171519.Vacation-Attraction) - [Cool Insuring Arena ](https://expedia.com/Cool-Insuring-Arena-Glens-Falls.d6210487.Vacation-Attraction) - [Wild West Ranch and Western Town ](https://expedia.com/Wild-West-Ranch-And-Western-Town-Lake-George.d6171522.Vacation-Attraction) - [Adirondack Outlet Mall ](https://expedia.com/Adirondack-Outlet-Mall-Lake-George.d6173782.Vacation-Attraction) - [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) - [French Mountain Commons ](https://expedia.com/French-Mountain-Commons-Lake-George.d6210994.Vacation-Attraction)