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Search results; Over 1,000 homes in Chestertown

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Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 private bathroom
20–25 Sept
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4.96 out of 5 average rating, 281 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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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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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 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
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, 59 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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Guest favourite
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Townhouse in Chestertown
Secluded and Cozy Townhome at Tripp Lake
3 bedrooms, 3 beds, 2.5 bathrooms
21–26 Sept
4.97 out of 5 average rating, 31 reviews
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Guest favourite
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Cabin in Chestertown
Posh Camp a Classic Adk Mtn. Cabin & Guide Srvc.
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
4.97 out of 5 average rating, 92 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
Home in Chestertown
Gorgeous 4BR Lakefront Friends Lake, NY - Dock
4 bedrooms, 6 beds, 3.5 bathrooms
18–23 Oct
4.88 out of 5 average rating, 60 reviews
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Top guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
2 bedrooms, 2 bathrooms
20–25 Sept
4.96 out of 5 average rating, 47 reviews
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Top guest favourite
Cabin in Chestertown
Pine Tree Cove on Friends Lake
4 bedrooms, 12 beds, 4 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 84 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, 80 reviews
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Guest favourite
Cottage in Chestertown
Private Dock & Beach! Lakefront, Fire Pit, Boats
2 bedrooms, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 7 reviews
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Home in Chestertown
Year-Round Loon Lake Retreat: Ski, Hike, Explore!
3 bedrooms, 6 beds, 3 bathrooms
21–26 Sept