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Search results; Over 1,000 homes in Chestertown

Descriptions are based on details hosts provide
Top guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms, 3 beds, 1 private bathroom
9–14 Aug
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4.95 out of 5 average rating, 261 reviews
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 bathroom
20–25 Jul
4.96 out of 5 average rating, 271 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, 68 reviews
Top guest favourite
Chalet in Chestertown
Chalet on Loon Lake (Gore Mt. 20 min.)
4 bedrooms, 5 beds, 2 bathrooms
17–22 Oct
4.98 out of 5 average rating, 175 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, 97 reviews
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Home in Chestertown
Adirondack house with lake and beach access
6 bedrooms, 8 beds, 3 bathrooms
19–24 Jul
4.68 out of 5 average rating, 260 reviews
Guest favourite
Cabin in Brant Lake
Log cabin with river access and canoe
3 bedrooms, 5 beds, 2 bathrooms
18–23 Jul
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Chestertown
Private beach, hot tub, and saltwater pool
4 bedrooms, 11 beds, 2.5 bathrooms
25–30 Jul
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Cabin in Warrensburg
Waterfall, fire pit, and trails out back
2 bedrooms, 5 beds, 1 bathroom
9–14 Nov
4.97 out of 5 average rating, 124 reviews
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
Four-season home with a fire pit
3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
4.93 out of 5 average rating, 41 reviews
Guest favourite
Chalet in Warrensburg
Mid-century modern chalet on Schroon River
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.95 out of 5 average rating, 63 reviews
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
Superhost
Chalet in Warrensburg
Off-grid chalet on 80 private acres
4 bedrooms, 5 beds, 3 bathrooms
29 Aug – 3 Sept
4.92 out of 5 average rating, 504 reviews
Guest favourite
Home in Chestertown
Rita's Place
3 bedrooms, 3 beds, 2 bathrooms
26–31 Aug
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Chestertown
Shore fun waterfront lake house Close to Gore Mtn.
3 bedrooms, 4 beds, 2 bathrooms
5–10 Sept
4.83 out of 5 average rating, 12 reviews
Top guest favourite
Cabin in North Creek
1920s cottage on 10 Adirondack acres
1 queen bed, 1 bathroom
26–31 Jul
4.9 out of 5 average rating, 280 reviews
Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 56 reviews