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Search results; Over 1,000 homes in Chestertown

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Guest favourite
Home in Chestertown
House in the Adirondacks, 15 min from Gore!
3 bedrooms, 5 beds, 2.5 private bathrooms
19–24 Sept
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4.91 out of 5 average rating, 44 reviews
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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
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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
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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, 58 reviews
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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
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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
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Guest favourite
Home in Chestertown
Mimi’s by the lake
6 bedrooms, 9 beds, 3 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 27 reviews
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Guest favourite
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Chalet in Chestertown
Chalet on Loon Lake (Gore Mt. 20 min.)
4 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
4.98 out of 5 average rating, 175 reviews
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Guest favourite
Townhouse in Chestertown
Secluded and Cozy Townhome at Tripp Lake
3 bedrooms, 3 beds, 2.5 bathrooms
19–24 Sept
4.97 out of 5 average rating, 31 reviews
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Guest favourite
Home in Chestertown
Serene Loon Lake Waterfront - Sleeps up to 10
4 bedrooms, 4 beds, 2.5 bathrooms
21–26 Sept
4.91 out of 5 average rating, 23 reviews
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Top guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
2 bedrooms, 2 bathrooms
18–23 Sept
4.96 out of 5 average rating, 47 reviews
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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
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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, 39 reviews
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Home in Chestertown
Enchanted Chestertown Getaway
3 bedrooms, 4 beds, 1.5 bathrooms
28 Oct – 2 Nov
New place to stay
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Guest favourite
Cottage in Chestertown
Private Dock & Beach! Lakefront, Fire Pit, Boats
2 bedrooms, 2 beds, 1 bathroom
18–23 Sept
5.0 out of 5 average rating, 6 reviews
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Home in Chestertown
Eagles Nest at Loon Lake near Gore Mountain
7 bedrooms, 11 beds, 4 bathrooms
4–9 Oct
4.9 out of 5 average rating, 146 reviews
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Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 bathroom
19–24 Sept
4.96 out of 5 average rating, 281 reviews