Chestertown Travel Guide
Tourist Guide
Visit Chestertown
Where to stay in Chestertown
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.
The Fern Lodge
46 Fiddlehead Bay Rd. Chestertown NY
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
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! (2 reviews)
The host, Bryce, responded in a quick manner whenever we reached out to him. The accommodations were homey, spacious, and it was a quick and easy walk from the parking space to the place. Would definitely stay there again.
Reviewed on 8 Feb 2026
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 ...
10/10 Exceptional! (115 reviews)
Great house. Great location
Reviewed on 4 Jan 2026
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.
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! (2 reviews)
The host, Bryce, responded in a quick manner whenever we reached out to him. The accommodations were homey, spacious, and it was a quick and easy walk from the parking space to the place. Would definitely stay there again.
Reviewed on 8 Feb 2026
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Chestertown NY
Stay at this apartment in Chestertown. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Friends Lake and Tripp Pond are located ...
10/10 Exceptional! (76 reviews)
Hosts on location are very friendly and go above and beyond to make the stay enjoyable . The girls love playing with the dogs pearl and ruby. Been coming for several years and plan to return.
Reviewed on 18 Feb 2026
Elizabeth. A Guest House Near Lake George.
Chestertown NY
Stay at this holiday home in Chestertown. Enjoy free Wi-Fi, private pools and a water park. Popular attractions Loon Lake Beach and Friends Lake are located ...
8.4/10 Very Good! (46 reviews)
Host was very helpful.
Reviewed on 17 Feb 2026
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.
Popular places to visit
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.
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.
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.
