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Search results; Over 1,000 homes in Chestertown

Top guest favourite
Chalet in Chestertown
Chalet on Loon Lake (Gore Mt. 20 min.)
4 bedrooms, 5 beds, 2 private bathrooms
18–23 Oct
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4.98 out of 5 average rating, 175 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, 267 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, 182 reviews
Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds, 2 bathrooms
26–31 Aug
5.0 out of 5 average rating, 59 reviews
Guest favourite
Townhouse in Chestertown
Secluded and Cozy Townhome at Tripp Lake
3 bedrooms, 3 beds, 2.5 bathrooms
29 Aug – 3 Sept
4.96 out of 5 average rating, 28 reviews
Cottage in Chestertown
Private Dock & Beach! Lakefront, Fire Pit, Boats
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Chestertown
Gorgeous 4BR Lakefront Friends Lake, NY | Dock
4 bedrooms, 6 beds, 3.5 bathrooms
13–18 Oct
4.88 out of 5 average rating, 60 reviews
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 bathroom
25–30 Aug
4.96 out of 5 average rating, 275 reviews
Top guest favourite
Home in Chestertown
Modern ADK House-Lake and Mountain View-Sleeps 16
4 bedrooms, 11 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 37 reviews
Superhost
Home in Chestertown
Child-friendly 3BR Adirondacks | Fireplace
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.89 out of 5 average rating, 57 reviews
Guest favourite
Cottage in Chestertown
Private Loon Lake property, cozy cabin on 3 Acres
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 55 reviews
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4 bedrooms, 7 beds, 3 bathrooms
30 Aug – 4 Sept
4.94 out of 5 average rating, 17 reviews
Guest favourite
Home in Chestertown
Shore fun waterfront lake house Close to Gore Mtn.
3 bedrooms, 4 beds, 2 bathrooms
5–10 Sept
4.88 out of 5 average rating, 16 reviews
Cabin in Chestertown
All-Season Family Retreat w/ Dock on Loon Lake!
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Home in Chestertown
Blue Bay Retreat - Loon Lake Lakefront w/ Hot Tub
4 bedrooms, 9 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 72 reviews
Home in Chestertown
Quiet Chestertown Escape | Nearby Gore & Lakes
3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.67 out of 5 average rating, 6 reviews
Guest favourite
Home in Chestertown
Adirondack Oasis, 15 Mi to Lake George Village!
3 bedrooms, 6 beds, 2 bathrooms
6–11 Sept
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Guest suite in Pottersville
Private Spacious Suite near Lakes, Peaks & WOL-BI
2 beds, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 172 reviews