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Search results; Over 1,000 homes in Chestertown

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Guest favourite
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
3 bedrooms, 4 beds, 2.5 private bathrooms
1–6 Sept
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4.91 out of 5 average rating, 46 reviews
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Guest favourite
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds
6–11 Sept
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms, 3 beds
6–11 Sept
4.96 out of 5 average rating, 270 reviews
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Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 61 reviews
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Top guest favourite
Home in Chestertown
The Stone Lodge on Blythewood Island on Loon Lake
4 bedrooms, 6 beds
27 Sept – 2 Oct
4.93 out of 5 average rating, 184 reviews
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Guest favourite
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds
9–14 Sept
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Home in Chestertown
Mimi’s by the lake
6 bedrooms, 9 beds
5–10 Oct
4.92 out of 5 average rating, 26 reviews
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Top guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
2 bedrooms
13–18 Sept
4.96 out of 5 average rating, 46 reviews
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Home in Chestertown
Enchanted Chestertown Getaway
3 bedrooms, 4 beds
28 Oct – 2 Nov
New place to stay
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Guest favourite
Cottage in Chestertown
Private Loon Lake property, cozy cabin on 3 Acres
2 bedrooms, 2 beds
20–25 Sept
4.93 out of 5 average rating, 57 reviews
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Guest favourite
Townhouse in Chestertown
Secluded and Cozy Townhome at Tripp Lake
3 bedrooms, 3 beds
17–22 Sept
4.97 out of 5 average rating, 30 reviews
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Guest favourite
Townhouse in Chestertown
Rustic Retreat
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 6 reviews
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Home in Chestertown
Quiet Chestertown Escape | Nearby Gore & Lakes
3 bedrooms, 4 beds
1–6 Dec
4.67 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Chestertown
Pond Farmhouse: Private Hot Tub, Fire Pit, Town
3 bedrooms, 6 beds
8–13 Sept
4.94 out of 5 average rating, 18 reviews
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Top guest favourite
Cabin in Chestertown
Pine Tree Cove on Friends Lake
4 bedrooms, 12 beds
7–12 Sept
4.98 out of 5 average rating, 83 reviews
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Top guest favourite
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
3 bedrooms, 7 beds
7–12 Sept
4.88 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Adirondack
Adirondack Owl's Nest Guest House
4 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 189 reviews
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Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4 bedrooms, 7 beds
13–18 Sept
4.94 out of 5 average rating, 17 reviews
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Home in Chestertown
Rustic Adirondacks Home w/ Hot Tub & Lake Access!
3 bedrooms, 5 beds
27 Sept – 2 Oct
4.87 out of 5 average rating, 83 reviews