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Search results; Over 1,000 homes in Chestertown

Guest favourite
Home in Chestertown
Adirondack 🏠 near Gore Mt, North Creek, Loon lake.
2 bedrooms, 6 beds, 2 private bathrooms
1–6 Aug
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4.92 out of 5 average rating, 120 reviews
Top guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
4.95 out of 5 average rating, 259 reviews
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
4.96 out of 5 average rating, 268 reviews
Guest favourite
Barn in Chestertown
Adirondack Base Camp by Loon Lake and Gore Mt.!
2 bedrooms, 7 beds, 1 bathroom
6–11 Sept
4.95 out of 5 average rating, 103 reviews
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
3 bedrooms, 7 beds, 3 bathrooms
26–31 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Cottage in Chestertown
Private Loon Lake property, cozy cabin on 3 Acres
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 53 reviews
Top guest favourite
Home in Chestertown
Cozy Adk Victorian! Ski, hike, hottub, relax!
4 bedrooms, 7 beds, 3 bathrooms
27 Jul – 1 Aug
4.97 out of 5 average rating, 67 reviews
Top guest favourite
Home in Adirondack
Adirondack Owl's Nest Guest House
4 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
5.0 out of 5 average rating, 181 reviews
Top guest favourite
Flat in Chestertown
Rustic Adirondack Studio Apartment
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 120 reviews
Guest favourite
Cabin in Brant Lake
ForeverWild Cabin- Close to LG, Firepit, Pavilion
3 bedrooms, 5 beds, 2 bathrooms
18–23 Jul
5.0 out of 5 average rating, 21 reviews
Guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
2 bedrooms, 2 bathrooms
6–11 Jul
4.95 out of 5 average rating, 42 reviews
Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds, 2 bathrooms
6–11 Jul
5.0 out of 5 average rating, 55 reviews
Home in Chestertown
Rustic Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
9–14 Aug
Guest favourite
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
3 bedrooms, 4 beds, 2.5 bathrooms
18–23 Jul
4.92 out of 5 average rating, 39 reviews
Top guest favourite
Chalet in Chestertown
The Roost, a lake front 4 season home
4 bedrooms, 7 beds, 3 bathrooms
13–18 Sept
4.98 out of 5 average rating, 65 reviews
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cabin in Warrensburg
Bearpine Cottage
2 bedrooms, 5 beds, 1 bathroom
11–16 Aug
4.97 out of 5 average rating, 123 reviews
Top guest favourite
Home in Warrensburg
River House
3 bedrooms, 8 beds, 2.5 bathrooms
31 Aug – 5 Sept
4.97 out of 5 average rating, 62 reviews
Guest favourite
Home in Chestertown
Shore fun waterfront lake house Close to Gore Mtn.
3 bedrooms, 4 beds, 2 bathrooms
25–30 Aug
4.83 out of 5 average rating, 12 reviews