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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
1–6 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, 264 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
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
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
Top guest favourite
Home in Chestertown
Modern ADK House-Lake and Mountain View-Sleeps 16
4 bedrooms, 11 beds, 2.5 bathrooms
22–27 Aug
5.0 out of 5 average rating, 35 reviews
Cottage in Chestertown
Private Dock & Beach! Lakefront, Fire Pit, Boats
2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
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
Cabin in Chestertown
Sleeps 10 | Adirondack Summer Escapes & Adventures
3 bedrooms, 6 beds, 3.5 bathrooms
15–20 Aug
4.94 out of 5 average rating, 16 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, 55 reviews
Guest favourite
Home in Chestertown
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.96 out of 5 average rating, 115 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
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
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
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
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
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
Top guest favourite
Flat in Chestertown
Rustic Adirondack Studio Apartment
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 120 reviews
Guest favourite
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
4.93 out of 5 average rating, 41 reviews