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Search results; Over 1,000 homes in Chestertown

Top guest favourite
Chalet in Chestertown
The Roost, a lake front 4 season home
4 bedrooms, 7 beds, 3 private bathrooms
16–21 Sept
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4.99 out of 5 average rating, 68 reviews
Guest favourite
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 273 reviews
Guest favourite
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
3 bedrooms, 7 beds, 3 bathrooms
16–21 Sept
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Chestertown
Rustic Adirondack Studio Apartment
1 bedroom, 1 queen bed, 1 bathroom
5–10 Oct
5.0 out of 5 average rating, 123 reviews
Guest favourite
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
3 bedrooms, 4 beds, 2.5 bathrooms
24–29 Sept
4.91 out of 5 average rating, 46 reviews
Top guest favourite
Home in Chestertown
Shore fun waterfront lake house Close to Gore Mtn.
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.9 out of 5 average rating, 21 reviews
Guest favourite
Home in Chestertown
House in the Adirondacks, 15 min from Gore!
3 bedrooms, 5 beds, 2.5 bathrooms
16–21 Sept
4.91 out of 5 average rating, 44 reviews
Guest favourite
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Cottage in Chestertown
Private Loon Lake property, cozy cabin on 3 Acres
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.93 out of 5 average rating, 57 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
4.94 out of 5 average rating, 185 reviews
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.96 out of 5 average rating, 280 reviews
Guest favourite
Townhouse in Chestertown
Secluded and Cozy Townhome at Tripp Lake
3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Sept
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Home in Chestertown
Blue Bay Retreat - Loon Lake Lakefront w/ Hot Tub
4 bedrooms, 9 beds, 2 bathrooms
19–24 Oct
5.0 out of 5 average rating, 79 reviews
Guest favourite
Flat in Chestertown
Lily Pad North at Loon Lake near Gore Mountain
2 bedrooms, 3 beds, 1 bathroom
17–22 Sept
4.81 out of 5 average rating, 143 reviews
Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 62 reviews
Superhost
Cottage in Chestertown
Friends Lake Adirondack Cottage
3 bedrooms, 4 beds, 1 bathroom
15–20 Sept
4.86 out of 5 average rating, 42 reviews
Home in Chestertown
Enchanted Chestertown Getaway
3 bedrooms, 4 beds, 1.5 bathrooms
28 Oct – 2 Nov
New place to stay
Guest favourite
Home in Chestertown
Family friendly Adirondack dream, no cleaning fee!
3 bedrooms, 5 beds, 2 bathrooms
21–26 Oct
4.93 out of 5 average rating, 101 reviews