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Search results; Over 1,000 homes in Chestertown

Top guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms, 3 beds, 1 private bathroom
9–14 Aug
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4.95 out of 5 average rating, 259 reviews
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
4.96 out of 5 average rating, 269 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Top guest favourite
Chalet in Chestertown
Chalet on Loon Lake (Gore Mt. 20 min.)
4.98 out of 5 average rating, 175 reviews, 4 bedrooms, 5 beds, 2 bathrooms
17–22 Oct
Top guest favourite
Home in Chestertown
Cozy Adk Victorian! Ski, hike, hottub, relax!
4.97 out of 5 average rating, 68 reviews, 4 bedrooms, 7 beds, 3 bathrooms
27 Jul – 1 Aug
Guest favourite
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
4.92 out of 5 average rating, 39 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
18–23 Jul
Top guest favourite
Home in Chestertown
The Hayes Homestead
5.0 out of 5 average rating, 56 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Superhost
Chalet in Warrensburg
Adirondack Chalet on 80 private acres
4.92 out of 5 average rating, 504 reviews, 4 bedrooms, 5 beds, 3 bathrooms
26–31 Jul
Cabin in Chestertown
Lake Cabin Retreat
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 6 beds, 2 bathrooms
22–27 Aug
Guest favourite
Cabin in Brant Lake
ForeverWild Cabin- Close to LG, Firepit, Pavilion
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 5 beds, 2 bathrooms
18–23 Jul
Guest favourite
Home in Chestertown
Family friendly Adirondack dream, no cleaning fee!
4.94 out of 5 average rating, 97 reviews, 3 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Cabin in Warrensburg
Bearpine Cottage
4.97 out of 5 average rating, 123 reviews, 2 bedrooms, 5 beds, 1 bathroom
11–16 Aug
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4.94 out of 5 average rating, 16 reviews, 4 bedrooms, 7 beds, 3 bathrooms
23–28 Aug
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
4.75 out of 5 average rating, 4 reviews, 3 bedrooms, 7 beds, 3 bathrooms
26–31 Jul
Guest favourite
Apartment in Chestertown
Evergreen Lakeside Adirondack Retreat
4.89 out of 5 average rating, 36 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
26–31 Aug
Top guest favourite
Home in Chestertown
Big Bear Lodge w/ Hot Tub and Sauna
4.93 out of 5 average rating, 70 reviews, 2 bedrooms, 6 beds, 1.5 bathrooms
15–20 Aug
Superhost
Cabin in Chestertown
Quaint Adirondack Condo
4.78 out of 5 average rating, 27 reviews, 1 bedroom, 3 beds, 1 bathroom
15–20 Aug
Top guest favourite
Cabin in Chestertown
Posh Camp a Classic Adk Mtn. Cabin & Guide Srvc.
4.99 out of 5 average rating, 86 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Jul
Top guest favourite
Home in Wevertown
A Cozy Creekside Getaway minutes from Gore Mtn.
4.97 out of 5 average rating, 164 reviews, 2 bedrooms, 2 beds, 2 bathrooms
13–18 Jul
Guest favourite
Home in Chestertown
Adirondack 🏠 near Gore Mt, North Creek, Loon lake.
4.92 out of 5 average rating, 120 reviews, 2 bedrooms, 6 beds, 2 bathrooms
1–6 Aug