Search results; Over 1,000 homes in Chestertown

Guest favourite
Cabin in Chestertown
Adirondack Private Lakefront Knotty Pine Cabin
3 bedrooms, 5 beds, 2 private bathrooms
14–19 Sept
,
4.81 out of 5 average rating, 93 reviews
Top guest favourite
Home in Chestertown
Adirondack Lake House
4.95 out of 5 average rating, 259 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4.93 out of 5 average rating, 15 reviews, 4 bedrooms, 7 beds, 3 bathrooms
23–28 Aug
Top guest favourite
Home in Chestertown
The Hayes Homestead
5.0 out of 5 average rating, 55 reviews, 3 bedrooms, 4 beds, 2 bathrooms
25–30 Jul
Top guest favourite
Chalet in Chestertown
Chalet on Loon Lake (Gore Mt. 20 min.)
4.98 out of 5 average rating, 174 reviews, 4 bedrooms, 5 beds, 2 bathrooms
17–22 Oct
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
4.96 out of 5 average rating, 267 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Chestertown
Cozy Adk Victorian! Ski, hike, hottub, relax!
4.97 out of 5 average rating, 66 reviews, 4 bedrooms, 7 beds, 3 bathrooms
9–14 Aug
Home in Chestertown
Quiet Chestertown Escape | Nearby Gore & Lakes
3 bedrooms, 4 beds, 2 bathrooms
6–11 Jul
Guest favourite
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
4.92 out of 5 average rating, 39 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
Guest favourite
Home in Chestertown
Gorgeous 4BR Lakefront Friends Lake, NY | Dock
4.88 out of 5 average rating, 60 reviews, 4 bedrooms, 6 beds, 3.5 bathrooms
16–21 Oct
Home in Chestertown
Eagles Nest at Loon Lake near Gore Mountain
4.92 out of 5 average rating, 142 reviews, 7 bedrooms, 16 beds, 4 bathrooms
1–6 Aug
Guest favourite
Home in Chestertown
Waterfront Pond/Walk To Town/Hot Tub/Fire Pit
4.9 out of 5 average rating, 10 reviews, 3 bedrooms, 6 beds, 1 bathroom
5–10 Jul
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
3 bedrooms, 7 beds, 3 bathrooms
5–10 Jul
Guest favourite
Home in Chestertown
Rita's Place
5.0 out of 5 average rating, 23 reviews, 3 bedrooms, 3 beds, 2 bathrooms
7–12 Jul
Home in Chestertown
Rustic Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
9–14 Aug
Guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
4.95 out of 5 average rating, 42 reviews, 2 bedrooms, 2 bathrooms
5–10 Jul
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
Top guest favourite
Chalet in Chestertown
The Roost, a lake front 4 season home
4.98 out of 5 average rating, 65 reviews, 4 bedrooms, 7 beds, 3 bathrooms
29 Jul – 3 Aug
Guest favourite
Cabin in Chestertown
Cozy Adirondack Cabin w/ Fire Pit & Lake Access
4.89 out of 5 average rating, 38 reviews, 4 bedrooms, 8 beds, 2 bathrooms
30 Aug – 4 Sept