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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, 261 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
4.96 out of 5 average rating, 271 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
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
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
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, 34 reviews, 4 bedrooms, 11 beds, 2.5 bathrooms
25–30 Jul
Top guest favourite
Cabin in Chestertown
Posh Camp a Classic Adk Mtn. Cabin & Guide Srvc.
4.99 out of 5 average rating, 88 reviews, 1 bedroom, 1 bed, 1 bathroom
14–19 Aug
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
8–13 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
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
Superhost
Chalet in Warrensburg
Adirondack Chalet on 80 private acres
4.92 out of 5 average rating, 505 reviews, 4 bedrooms, 5 beds, 3 bathrooms
29 Aug – 3 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
Top guest favourite
Cabin in Warrensburg
Bearpine Cottage
4.97 out of 5 average rating, 124 reviews, 2 bedrooms, 5 beds, 1 bathroom
9–14 Nov
Guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
4.95 out of 5 average rating, 42 reviews, 2 bedrooms, 2 bathrooms
22–29 Aug
Top guest favourite
Home in Chestertown
Big Bear Lodge w/ Hot Tub and Sauna
4.93 out of 5 average rating, 73 reviews, 2 bedrooms, 6 beds, 1.5 bathrooms
6–11 Sept
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
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