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Search results; Over 1,000 homes in Chestertown

Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 private bathroom
24–29 Aug
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4.96 out of 5 average rating, 273 reviews
Top guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms, 3 beds, 1 bathroom
26–31 Aug
4.95 out of 5 average rating, 265 reviews
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 4 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, 28 reviews
Cottage in Chestertown
Private Dock & Beach! Lakefront, Fire Pit, Boats
2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Home in Chestertown
Gorgeous 4BR Lakefront Friends Lake, NY | Dock
4 bedrooms, 6 beds, 3.5 bathrooms
9–14 Oct
4.88 out of 5 average rating, 60 reviews
Superhost
Home in Chestertown
Child-friendly 3BR Adirondacks | Fireplace
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.89 out of 5 average rating, 56 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
The Curley Cabin
3 bedrooms, 3 beds, 1 bathroom
1–6 Sept
New place to stay
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, 58 reviews
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4 bedrooms, 7 beds, 3 bathrooms
30 Aug – 4 Sept
4.94 out of 5 average rating, 16 reviews
Superhost
Home in Chestertown
Forest Lake Haven Main House
3 bedrooms, 5 beds, 3 bathrooms
10–15 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Chestertown
The Stone Lodge on Blythewood Island on Loon Lake
4 bedrooms, 6 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 181 reviews
Guest favourite
Home in Chestertown
House in the Adirondacks, 15 min from Gore!
3 bedrooms, 5 beds, 2.5 bathrooms
28 Aug – 2 Sept
4.93 out of 5 average rating, 42 reviews
Top guest favourite
Home in Chestertown
Blue Bay Retreat - Loon Lake Lakefront w/ Hot Tub
4 bedrooms, 9 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 72 reviews
Superhost
Cottage in Chestertown
Friends Lake Adirondack Cottage
3 bedrooms, 4 beds, 1 bathroom
18–23 Aug
4.85 out of 5 average rating, 40 reviews
Guest favourite
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
3 bedrooms, 7 beds, 3 bathrooms
22–27 Aug
4.83 out of 5 average rating, 6 reviews
Top guest favourite
Home in Adirondack
Adirondack Owl's Nest Guest House
4 bedrooms, 4 beds, 2 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 184 reviews
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 3 reviews