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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
17–22 Oct
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4.98 out of 5 average rating, 175 reviews
Top guest favourite
Home in Chestertown
Adirondack Lake House
4.95 out of 5 average rating, 262 reviews, 2 bedrooms, 3 beds, 1 bathroom
26–31 Aug
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
4.96 out of 5 average rating, 272 reviews, 2 bedrooms, 3 beds, 1 bathroom
20–25 Jul
Cabin in Chestertown
Lake Cabin Retreat
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
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
Top guest favourite
Home in Chestertown
Modern ADK House-Lake and Mountain View-Sleeps 16
5.0 out of 5 average rating, 35 reviews, 4 bedrooms, 11 beds, 2.5 bathrooms
25–30 Jul
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
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
Home in Chestertown
The Stone Lodge on Blythewood Island on Loon Lake
4.93 out of 5 average rating, 181 reviews, 4 bedrooms, 6 beds, 2.5 bathrooms
27 Sept – 2 Oct
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
Guest favourite
Cabin in Brant Lake
ForeverWild Cabin- Close to LG, Firepit, Pavilion
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 5 beds, 2 bathrooms
21–26 Jul
Superhost
Chalet in Warrensburg
Adirondack Chalet on 80 private acres
4.92 out of 5 average rating, 507 reviews, 4 bedrooms, 5 beds, 3 bathrooms
29 Aug – 3 Sept
Guest favourite
Home in Chestertown
House in the Adirondacks, 15 min from Gore!
4.93 out of 5 average rating, 42 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
28 Aug – 2 Sept
Guest favourite
Home in Chestertown
Shore fun waterfront lake house Close to Gore Mtn.
4.85 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 2 bathrooms
5–10 Sept
Guest favourite
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
4.93 out of 5 average rating, 41 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
Top guest favourite
Home in Adirondack
Adirondack Owl's Nest Guest House
5.0 out of 5 average rating, 183 reviews, 4 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
Guest favourite
Home in Chestertown
Rita's Place
5.0 out of 5 average rating, 23 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Aug
Guest favourite
Barn in Chestertown
Adirondack Base Camp by Loon Lake and Gore Mt.!
4.95 out of 5 average rating, 103 reviews, 2 bedrooms, 7 beds, 1 bathroom
6–11 Sept
Guest favourite
Chalet in Chestertown
Loon Lake Luxury with Kayaks, Canoe, Hot Tub
4.91 out of 5 average rating, 56 reviews, 3 bedrooms, 6 beds, 3 bathrooms
8–13 Aug