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Search results; Over 1,000 homes in Chestertown

Guest favourite
Home in Chestertown
Adirondack 🏠 near Gore Mt, North Creek, Loon lake.
2 bedrooms, 6 beds, 2 private bathrooms
5–10 Jul
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4.92 out of 5 average rating, 120 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
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
The Hayes Homestead
5.0 out of 5 average rating, 55 reviews, 3 bedrooms, 4 beds, 2 bathrooms
5–10 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
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
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4.94 out of 5 average rating, 16 reviews, 4 bedrooms, 7 beds, 3 bathrooms
23–28 Aug
Cabin in Chestertown
Lake Cabin Retreat
New place to stay, 3 bedrooms, 6 beds, 2 bathrooms
5–10 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
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
3 bedrooms, 7 beds, 3 bathrooms
5–10 Jul
Superhost
Chalet in Warrensburg
Adirondack Chalet on 80 private acres
4.92 out of 5 average rating, 504 reviews, 4 bedrooms, 5 beds, 3 bathrooms
9–14 Aug
Guest favourite
Cabin in Chestertown
Cozy Adirondack Cabin w/ Fire Pit & Lake Access
4.9 out of 5 average rating, 39 reviews, 4 bedrooms, 8 beds, 2 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Chestertown
Family friendly Adirondack dream, no cleaning fee!
4.94 out of 5 average rating, 96 reviews, 3 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
Guest favourite
Townhouse in Chestertown
Secluded and Cozy Townhome at Tripp Lake
4.96 out of 5 average rating, 27 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
22–27 Aug
Guest favourite
Cabin in Brant Lake
ForeverWild Cabin- Close to LG, Firepit, Pavilion
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 5 beds, 2 bathrooms
18–23 Jul
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
Guest favourite
Home in Chestertown
Shore fun waterfront lake house Close to Gore Mtn.
4.82 out of 5 average rating, 11 reviews, 3 bedrooms, 4 beds, 2 bathrooms
25–30 Aug
Guest favourite
Home in Chestertown
Waterfront Pond/Walk To Town/Hot Tub/Fire Pit
4.91 out of 5 average rating, 11 reviews, 3 bedrooms, 6 beds, 1 bathroom
5–10 Jul
Top guest favourite
Cabin in Warrensburg
Bearpine Cottage
4.97 out of 5 average rating, 123 reviews, 2 bedrooms, 5 beds, 1 bathroom
26–31 Oct