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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, 260 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
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
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, 270 reviews
Guest favourite
Townhouse in Chestertown
Secluded and Cozy Townhome at Tripp Lake
3 bedrooms, 3 beds, 2.5 bathrooms
11–16 Jul
4.96 out of 5 average rating, 27 reviews
Guest favourite
Barn in Chestertown
Adirondack Base Camp by Loon Lake and Gore Mt.!
2 bedrooms, 7 beds, 1 bathroom
17–22 Aug
4.95 out of 5 average rating, 103 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, 63 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 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, 68 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
Top guest favourite
Home in Pottersville
Bring Your Dog | River Dock + Fire Table
2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Chestertown
Forest Lake Haven Main House
3 bedrooms, 5 beds, 3 bathrooms
29 Jul – 4 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Chestertown
House in the Adirondacks, 15 min from Gore!
3 bedrooms, 5 beds, 2.5 bathrooms
22–27 Aug
4.93 out of 5 average rating, 42 reviews
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4 bedrooms, 7 beds, 3 bathrooms
23–28 Aug
4.94 out of 5 average rating, 16 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
Home in Warrensburg
Lake George | Hot Tub | Firepit | Schroon Lake
2 bedrooms, 4 beds, 1.5 bathrooms
9–14 Aug
4.98 out of 5 average rating, 159 reviews
Guest favourite
Home in Chestertown
Family friendly Adirondack dream, no cleaning fee!
3 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
4.94 out of 5 average rating, 97 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