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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
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4.81 out of 5 average rating, 93 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
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
3 bedrooms, 7 beds, 3 bathrooms
5–10 Jul
Top guest favourite
Home in Chestertown
Cozy Adk Victorian! Ski, hike, hottub, relax!
4 bedrooms, 7 beds, 3 bathrooms
9–14 Aug
4.97 out of 5 average rating, 66 reviews
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
4.96 out of 5 average rating, 266 reviews
Guest favourite
Home in Chestertown
Adirondack Oasis, 15 Mi to Lake George Village!
3 bedrooms, 6 beds, 2 bathrooms
24–29 Jul
4.97 out of 5 average rating, 31 reviews
Guest favourite
Home in Chestertown
Adirondack 🏠 near Gore Mt, North Creek, Loon lake.
2 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
4.92 out of 5 average rating, 120 reviews
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
New place to stay
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4 bedrooms, 7 beds, 3 bathrooms
23–28 Aug
4.93 out of 5 average rating, 14 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
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
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
28 Jul – 2 Aug
New place to stay
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
Home in Chestertown
Rustic Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
12–17 Jul
Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds, 2 bathrooms
25–30 Jul
5.0 out of 5 average rating, 54 reviews
Superhost
Chalet in Warrensburg
Adirondack Chalet on 80 private acres
4 bedrooms, 5 beds, 3 bathrooms
9–14 Aug
4.92 out of 5 average rating, 504 reviews
Guest favourite
Chalet in Chestertown
The Roost, a lake front 4 season home
4 bedrooms, 7 beds, 3 bathrooms
29 Jul – 3 Aug
4.98 out of 5 average rating, 64 reviews
Cabin in Chestertown
Meadow House
5 bedrooms, 9 beds, 3 bathrooms
11–16 Jul
4.88 out of 5 average rating, 161 reviews
Top guest favourite
Cabin in Schroon Lake
The Treehouse
2 bedrooms, 4 beds, 1 bathroom
12–17 Sept
4.98 out of 5 average rating, 114 reviews