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Search results; Over 1,000 homes in Chestertown

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Top guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
2 bedrooms, 2 private bathrooms
17–22 Oct
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4.96 out of 5 average rating, 47 reviews
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Top guest favourite
Chalet in Chestertown
Chalet on Loon Lake (Gore Mt. 20 min.)
5 beds
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
3 beds
4–9 Oct
4.96 out of 5 average rating, 274 reviews
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Top guest favourite
Home in Chestertown
The Stone Lodge on Blythewood Island on Loon Lake
6 beds
4–9 Oct
4.94 out of 5 average rating, 185 reviews
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Top guest favourite
Home in Chestertown
Shore fun waterfront lake house Close to Gore Mtn.
4 beds
3–8 Oct
4.91 out of 5 average rating, 22 reviews
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Guest favourite
Cabin in Chestertown
Lake Cabin Retreat
6 beds
1–6 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Chestertown
The Hayes Homestead
4 beds
4–9 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
5 beds
1–6 Oct
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Cottage in Chestertown
Private Loon Lake property, cozy cabin on 3 Acres
2 beds
4–9 Oct
4.93 out of 5 average rating, 60 reviews
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Top guest favourite
Cabin in Chestertown
Pine Tree Cove on Friends Lake
12 beds
1–6 Oct
4.98 out of 5 average rating, 84 reviews
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Guest favourite
Townhouse in Chestertown
Secluded and Cozy Townhome at Tripp Lake
3 beds
6–11 Oct
4.97 out of 5 average rating, 31 reviews
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Top guest favourite
Home in Chestertown
Blue Bay Retreat - Loon Lake Lakefront w/ Hot Tub
9 beds
19–24 Oct
5.0 out of 5 average rating, 80 reviews
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Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
7 beds
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
11 beds
4–9 Oct
4.9 out of 5 average rating, 146 reviews
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Guest favourite
Home in Chestertown
Gorgeous 4BR Lakefront Friends Lake, NY - Dock
6 beds
18–23 Oct
4.88 out of 5 average rating, 60 reviews
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Top guest favourite
Home in Chestertown
Modern ADK House-Lake and Mountain View-Sleeps 16
11 beds
18–23 Oct
5.0 out of 5 average rating, 39 reviews
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Guest favourite
Home in Chestertown
Serene Loon Lake Waterfront - Sleeps up to 10
4 beds
1–6 Oct
4.91 out of 5 average rating, 23 reviews
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Guest favourite
Home in Chestertown
Rita's Place
3 beds
5–10 Oct
5.0 out of 5 average rating, 24 reviews
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Guest favourite
Home in Chestertown
Mimi’s by the lake
9 beds
4–9 Oct
4.93 out of 5 average rating, 27 reviews