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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
12–17 Oct
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4.96 out of 5 average rating, 281 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
4–9 Oct
4.96 out of 5 average rating, 274 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
3–8 Oct
4.91 out of 5 average rating, 22 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
4–9 Oct
4.94 out of 5 average rating, 185 reviews
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Guest favourite
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Cottage in Chestertown
Private Loon Lake property, cozy cabin on 3 Acres
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.93 out of 5 average rating, 60 reviews
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Guest favourite
Townhouse in Chestertown
Secluded and Cozy Townhome at Tripp Lake
3 bedrooms, 3 beds, 2.5 bathrooms
6–11 Oct
4.97 out of 5 average rating, 31 reviews
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Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4 bedrooms, 7 beds, 3 bathrooms
4–9 Oct
4.95 out of 5 average rating, 21 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
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 62 reviews
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Guest favourite
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 8 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, 81 reviews
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Guest favourite
Home in Chestertown
Mossy Bear Retreat
3 bedrooms, 4 beds, 1 bathroom
1–6 Oct
4.82 out of 5 average rating, 17 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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Guest favourite
Home in Chestertown
Mimi’s by the lake
6 bedrooms, 9 beds, 3 bathrooms
4–9 Oct
4.93 out of 5 average rating, 27 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
1–6 Oct
4.91 out of 5 average rating, 23 reviews
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Superhost
Home in Chestertown
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
3 bedrooms, 5 beds, 2 bathrooms
23–28 Oct
4.93 out of 5 average rating, 117 reviews
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Home in Chestertown
Year-Round Loon Lake Retreat: Ski, Hike, Explore!
3 bedrooms, 6 beds, 3 bathrooms
1–6 Oct