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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
4.95 out of 5 average rating, 265 reviews, 2 bedrooms, 3 beds, 1 bathroom
26–31 Aug
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4.94 out of 5 average rating, 16 reviews, 4 bedrooms, 7 beds, 3 bathrooms
30 Aug – 4 Sept
Cabin in Chestertown
Lake Cabin Retreat
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
Cottage in Chestertown
Private Dock & Beach! Lakefront, Fire Pit, Boats
2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Cabin in Chestertown
Sleeps 10 | Adirondack Summer Escapes & Adventures
4.94 out of 5 average rating, 16 reviews, 3 bedrooms, 6 beds, 3.5 bathrooms
15–20 Aug
Guest favourite
Home in Chestertown
Family friendly Adirondack dream, no cleaning fee!
4.94 out of 5 average rating, 97 reviews, 3 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Home in Chestertown
Modern ADK House-Lake and Mountain View-Sleeps 16
5.0 out of 5 average rating, 35 reviews, 4 bedrooms, 11 beds, 2.5 bathrooms
22–27 Aug
Superhost
Home in Chestertown
Child-friendly 3BR Adirondacks | Fireplace
4.89 out of 5 average rating, 55 reviews, 3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
Guest favourite
Townhouse in Chestertown
Secluded and Cozy Townhome at Tripp Lake
4.96 out of 5 average rating, 28 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
22–27 Aug
Guest favourite
Home in Chestertown
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
4.96 out of 5 average rating, 115 reviews, 3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
Guest favourite
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
4.83 out of 5 average rating, 6 reviews, 3 bedrooms, 7 beds, 3 bathrooms
22–27 Aug
Guest favourite
Home in Chestertown
House in the Adirondacks, 15 min from Gore!
4.93 out of 5 average rating, 42 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
28 Aug – 2 Sept
Guest favourite
Home in Chestertown
Gorgeous 4BR Lakefront Friends Lake, NY | Dock
4.88 out of 5 average rating, 60 reviews, 4 bedrooms, 6 beds, 3.5 bathrooms
9–14 Oct
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Home in Chestertown
The Hayes Homestead
5.0 out of 5 average rating, 58 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Guest favourite
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
4.93 out of 5 average rating, 41 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
Superhost
Home in Chestertown
The Ramblewood. Family Friendly.
4.68 out of 5 average rating, 260 reviews, 6 bedrooms, 8 beds, 3 bathrooms
16–21 Aug
Top guest favourite
Flat in Chestertown
Rustic Adirondack Studio Apartment
5.0 out of 5 average rating, 120 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct