Title: Chestertown Travel Guide: Best of Chestertown, New York Travel 2026 | Expedia.co.uk [Hotels in Chestertown](https://expedia.co.uk/Chestertown-Hotels.d89045.Travel-Guide-Hotels)[Holiday Rentals in Chestertown](https://expedia.co.uk/Chestertown-Holiday-Rentals.d89045.Travel-Guide-HolidayRentals)[Chestertown Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chestertown.d89045.Car-Hire-Guide)[Chestertown Holidays](https://expedia.co.uk/Chestertown.d89045.Holidays-City-Breaks) # Chestertown Travel Guide ## Tourist 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) ![Chestertown](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 ### 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 While Chester Shores isn't home to many top sights, Loon Lake Beach and Loon Lake are some notable places to visit nearby. [](https://expedia.co.uk/Lake-George-Chester-Shores.dx553248635976471458) - Top hotels in Chestertown - Top Holiday 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 £334 29 Mar - 30 Mar includes taxes & fees Stay at this beach B&B in Chestertown. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Friends Lake and Loon Lake Beach are located ... 10/10 Exceptional! (52 reviews) I cannot say enough good things about the Fern Lodge. Beautiful atmosphere, wonderful host. Will be returning! Reviewed on 27 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%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 Stay at this family-friendly holiday home in Chestertown. Enjoy a garden, laundry facilities and a pool table. Popular attractions Loon Lake and Loon Lake Beach ... [Get rates](https://expedia.co.uk/Hotel-Search?startDate=10%2F04%2F2026&endDate=11%2F04%2F2026&selected=18956145&PinnedHotelID=18956145&HadPinnedHotel=true®ionId=89045) [](https://expedia.co.uk/Hotel-Search?startDate=10%2F04%2F2026&endDate=11%2F04%2F2026&selected=18956145&PinnedHotelID=18956145&HadPinnedHotel=true®ionId=89045) ![Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.](https://images.trvl-media.com/lodging/121000000/120760000/120755100/120755074/be8d3406_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure. Chestertown NY Stay at this holiday home in Chestertown. Enjoy free Wi-Fi, tennis courts and patios. Popular attractions Tripp Pond and Pack Demonstration Forest are located ... 10/10 Exceptional! (3 reviews) This was our first vacation rental as we were reluctant to try it after reading horrible stores about hidden fees and a tons of house cleaning list. We took a plunge this time and I am glad we did it. If you cook a lot (not us), a large party (not us), then this is perfect. It was a bit too big for ... Reviewed on 25 Mar 2026 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=10%2F04%2F2026&endDate=11%2F04%2F2026&selected=120755074&PinnedHotelID=120755074&HadPinnedHotel=true®ionId=89045) [](https://expedia.co.uk/Hotel-Search?startDate=10%2F04%2F2026&endDate=11%2F04%2F2026&selected=120755074&PinnedHotelID=120755074&HadPinnedHotel=true®ionId=89045) [See all 1,532 properties in Chestertown](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=28%2F03%2F2026&endDate=29%2F03%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. ![Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.](https://images.trvl-media.com/lodging/121000000/120760000/120755100/120755074/be8d3406_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure. Chestertown NY Stay at this holiday home in Chestertown. Enjoy free Wi-Fi, tennis courts and patios. Popular attractions Tripp Pond and Pack Demonstration Forest are located ... 10/10 Exceptional! (3 reviews) This was our first vacation rental as we were reluctant to try it after reading horrible stores about hidden fees and a tons of house cleaning list. We took a plunge this time and I am glad we did it. If you cook a lot (not us), a large party (not us), then this is perfect. It was a bit too big for ... Reviewed on 25 Mar 2026 [](https://expedia.co.uk/Chestertown-Hotels-Secluded-And-Cozy-Lakeside-Townhome-On-Tripp-Lake.h120755074.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 Stay at this family-friendly holiday home in Chestertown. Enjoy a garden, laundry facilities and a pool table. Popular attractions Loon Lake and Loon Lake Beach ... [](https://expedia.co.uk/Chestertown-Hotels-Eagles-Nest-At-Loon-Lake-Near-Gore-Mountain.h18956145.Hotel-Information) ![Charming 4 Bedroom Home In Lake Luzerne. 10 miles to Lake George Village.](https://images.trvl-media.com/lodging/34000000/33580000/33570300/33570223/42334a87_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Charming 4 Bedroom Home In Lake Luzerne. 10 miles to Lake George Village. Lake Luzerne NY Stay at this family-friendly holiday home in Lake Luzerne. Enjoy laundry facilities, a pool table and patios. Our guests praise the helpful staff in their reviews. ... 10/10 Exceptional! (216 reviews) This property is fantastic. Sooooo much room 4 spacious bedrooms. One n the lower floor is a full suite. We went with my whole family. 1 couple and 1 year old in bottom floor suite, 2 adult kids if n the bunk room and 1 adult child in huge master. Parents on second floor with our own bathroom. 3 ... Reviewed on 3 Mar 2026 [](https://expedia.co.uk/Lake-George-Hotels-Charming-4-Bedroom-Home-In-Lake-Luzerne.h33570223.Hotel-Information) [See all properties in Chestertown](https://expedia.co.uk/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.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2026-03-27&endDate=2026-03-28)[27 Mar - 28 Mar](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2026-03-27&endDate=2026-03-28) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2026-03-28&endDate=2026-03-29)[28 Mar - 29 Mar](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=2026-03-28&endDate=2026-03-29) [This weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=27%2F03%2F2026&endDate=29%2F03%2F2026)[27 Mar - 29 Mar](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=89045&startDate=27%2F03%2F2026&endDate=29%2F03%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.co.uk/Loon-Lake-Lake-George.d553248635976196050.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.co.uk/Friends-Lake-Lake-George.d553248635976195601.Attraction) #### Loon Lake Beach If a restful holiday is part of your travel plans, Loon Lake Beach might be the perfect place to visit during your trip to Chestertown. While you're in the area, stroll along the lakeside. [](https://expedia.co.uk/Loon-Lake-Beach-Chestertown.d553248621554184980.Attraction) ## 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 ![Brant Lake in the Adirondacks](https://images.trvl-media.com/place/6347839/ec89bf19-c189-4273-ba0b-d60b36e3703f.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Brant Lake - Cities near Chestertown - Places of interest [Bolton Landing](https://expedia.co.uk/Bolton-Landing.dx55597)[North Creek](https://expedia.co.uk/North-Creek.dx139117)[Warrensburg](https://expedia.co.uk/Warrensburg.dx171313)[Brant Lake](https://expedia.co.uk/Brant-Lake.dx6347839)[Pottersville](https://expedia.co.uk/Pottersville.dx6349845) - [Fort William Henry Museum ](https://expedia.co.uk/Fort-William-Henry-Museum-Lake-George.d6064463.Attraction) - [Wild West Ranch and Western Town ](https://expedia.co.uk/Wild-West-Ranch-And-Western-Town-Lake-George.d6171522.Attraction) - [Hiland Golf and Country Club ](https://expedia.co.uk/Hiland-Golf-And-Country-Club-Queensbury.d6171692.Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in 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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