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Search results; Over 1,000 homes in Chestertown

Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds, 2 private bathrooms
4–9 Oct
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5.0 out of 5 average rating, 60 reviews
Top guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
4.96 out of 5 average rating, 269 reviews
Guest favourite
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 6 reviews
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
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
4.93 out of 5 average rating, 183 reviews
Cabin in Chestertown
The Curley Cabin
3 bedrooms, 3 beds, 1 bathroom
1–6 Sept
New place to stay
Guest favourite
Townhouse in Chestertown
Rustic Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 5 reviews
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, 57 reviews
Top guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
2 bedrooms, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 45 reviews
Guest favourite
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 6 reviews
Cottage in Chestertown
Private Dock & Beach! Lakefront, Fire Pit, Boats
2 bedrooms, 2 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
3 bedrooms, 7 beds, 3 bathrooms
13–18 Sept
4.88 out of 5 average rating, 8 reviews
Guest favourite
Townhouse in Chestertown
Secluded and Cozy Townhome at Tripp Lake
3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Sept
4.97 out of 5 average rating, 29 reviews
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4 bedrooms, 7 beds, 3 bathrooms
13–18 Sept
4.94 out of 5 average rating, 17 reviews
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, 37 reviews
Top guest favourite
Home in Chestertown
Pond Farmhouse: Private Hot Tub, Fire Pit, Town
3 bedrooms, 5 beds, 1 bathroom
8–13 Sept
4.94 out of 5 average rating, 16 reviews
Guest favourite
Home in Chestertown
Mimi’s by the lake
6 bedrooms, 9 beds, 3 bathrooms
5–10 Oct
4.92 out of 5 average rating, 26 reviews
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 277 reviews
Guest favourite
Apartment in Chestertown
Evergreen Lakeside Adirondack Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
2–7 Sept
4.89 out of 5 average rating, 37 reviews