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Search results; Over 1,000 homes in Chestertown

Guest favourite
Cottage in Chestertown
Private Loon Lake property, cozy cabin on 3 Acres
2 bedrooms, 2 beds, 1 private bathroom
20–25 Sept
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4.93 out of 5 average rating, 57 reviews
Guest favourite
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
4.96 out of 5 average rating, 271 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, 61 reviews
Guest favourite
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 7 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, 184 reviews
Top guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
2 bedrooms, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 46 reviews
Guest favourite
Home in Chestertown
Mimi’s by the lake
6 bedrooms, 9 beds, 3 bathrooms
5–10 Oct
4.92 out of 5 average rating, 26 reviews
Home in Chestertown
Enchanted Chestertown Getaway
3 bedrooms, 4 beds, 1.5 bathrooms
28 Oct – 2 Nov
New place to stay
Top guest favourite
Home in Chestertown
Shore fun waterfront lake house Close to Gore Mtn.
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.89 out of 5 average rating, 19 reviews
Top guest favourite
Cabin in Chestertown
Pine Tree Cove on Friends Lake
4 bedrooms, 12 beds, 4 bathrooms
7–12 Sept
4.98 out of 5 average rating, 83 reviews
Top guest favourite
Home in Chestertown
Modern ADK House-Lake and Mountain View-Sleeps 16
4 bedrooms, 11 beds, 2.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 38 reviews
Top guest favourite
Home in Chestertown
Pond Farmhouse: Private Hot Tub, Fire Pit, Town
3 bedrooms, 6 beds, 1 bathroom
8–13 Sept
4.94 out of 5 average rating, 18 reviews
Guest favourite
Home in Chestertown
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 115 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
Guest favourite
Home in Chestertown
House in the Adirondacks, 15 min from Gore!
3 bedrooms, 5 beds, 2.5 bathrooms
8–13 Sept
4.93 out of 5 average rating, 43 reviews
Home in Chestertown
Rustic Adirondacks Home w/ Hot Tub & Lake Access!
3 bedrooms, 5 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.87 out of 5 average rating, 83 reviews
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4 bedrooms, 7 beds, 3 bathrooms
13–18 Sept
4.94 out of 5 average rating, 17 reviews
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 280 reviews