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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
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
4.95 out of 5 average rating, 259 reviews
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
4.96 out of 5 average rating, 267 reviews
Top guest favourite
Home in Chestertown
Cozy Adk Victorian! Ski, hike, hottub, relax!
4 bedrooms, 7 beds, 3 bathrooms
27 Jul – 1 Aug
4.97 out of 5 average rating, 66 reviews
Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 55 reviews
Guest favourite
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
4.92 out of 5 average rating, 39 reviews
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds, 2 bathrooms
22–27 Aug
New place to stay
Top guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4 bedrooms, 7 beds, 3 bathrooms
23–28 Aug
4.94 out of 5 average rating, 16 reviews
Guest favourite
Home in Chestertown
Rita's Place
3 bedrooms, 3 beds, 2 bathrooms
7–12 Jul
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Chestertown
Family friendly Adirondack dream, no cleaning fee!
3 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
4.94 out of 5 average rating, 96 reviews
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
3 bedrooms, 7 beds, 3 bathrooms
5–10 Jul
Guest favourite
Cabin in Chestertown
Cozy Adirondack Cabin w/ Fire Pit & Lake Access
4 bedrooms, 8 beds, 2 bathrooms
30 Aug – 4 Sept
4.9 out of 5 average rating, 39 reviews
Guest favourite
Home in Chestertown
Big Bear Lodge w/ Hot Tub and Sauna
2 bedrooms, 6 beds, 1.5 bathrooms
15–20 Aug
4.93 out of 5 average rating, 68 reviews
Top guest favourite
Home in Pottersville
Bring Your Dog | River Dock + Fire Table
2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Chestertown
Waterfront Pond/Walk To Town/Hot Tub/Fire Pit
3 bedrooms, 6 beds, 1 bathroom
5–10 Jul
4.91 out of 5 average rating, 11 reviews
Guest favourite
Cabin in Brant Lake
ForeverWild Cabin- Close to LG, Firepit, Pavilion
3 bedrooms, 5 beds, 2 bathrooms
18–23 Jul
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Cabin in Warrensburg
Bearpine Cottage
2 bedrooms, 5 beds, 1 bathroom
26–31 Oct
4.97 out of 5 average rating, 123 reviews
Guest favourite
Home in Chestertown
Shore fun waterfront lake house Close to Gore Mtn.
3 bedrooms, 4 beds, 2 bathrooms
25–30 Aug
4.82 out of 5 average rating, 11 reviews
Guest favourite
Townhouse in Chestertown
Secluded and Cozy Townhome at Tripp Lake
3 bedrooms, 3 beds, 2.5 bathrooms
22–27 Aug
4.96 out of 5 average rating, 27 reviews