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Search results; Over 1,000 homes in Chestertown

Guest favourite
Chalet in Chestertown
Loon Lake Luxury with Kayaks, Canoe, Hot Tub
3 bedrooms, 6 beds, 3 private bathrooms
8–13 Aug
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4.91 out of 5 average rating, 56 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, 261 reviews
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 bathroom
20–25 Jul
4.96 out of 5 average rating, 271 reviews
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 4 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
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
Chalet in Chestertown
Chalet on Loon Lake (Gore Mt. 20 min.)
4 bedrooms, 5 beds, 2 bathrooms
17–22 Oct
4.98 out of 5 average rating, 175 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
Top guest favourite
Cabin in Chestertown
Posh Camp a Classic Adk Mtn. Cabin & Guide Srvc.
1 bedroom, 1 queen bed, 1 bathroom
14–19 Aug
4.99 out of 5 average rating, 88 reviews
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
Superhost
Chalet in Warrensburg
Adirondack Chalet on 80 private acres
4 bedrooms, 5 beds, 3 bathrooms
29 Aug – 3 Sept
4.92 out of 5 average rating, 505 reviews
Top guest favourite
Cabin in Warrensburg
Bearpine Cottage
2 bedrooms, 5 beds, 1 bathroom
9–14 Nov
4.97 out of 5 average rating, 124 reviews
Top guest favourite
Home in Chestertown
Modern ADK House-Lake and Mountain View-Sleeps 16
4 bedrooms, 11 beds, 2.5 bathrooms
25–30 Jul
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 56 reviews
Guest favourite
Home in Chestertown
House in the Adirondacks, 15 min from Gore!
3 bedrooms, 5 beds, 2.5 bathrooms
28 Aug – 2 Sept
4.93 out of 5 average rating, 42 reviews
Guest favourite
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
4.93 out of 5 average rating, 41 reviews
Top guest favourite
Home in Chestertown
Big Bear Lodge w/ Hot Tub and Sauna
2 bedrooms, 6 beds, 1.5 bathrooms
6–11 Sept
4.93 out of 5 average rating, 73 reviews
Top guest favourite
Home in Chestertown
The Stone Lodge on Blythewood Island on Loon Lake
4 bedrooms, 6 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 181 reviews
Top guest favourite
Home in Chestertown
Waterfront Pond/Walk To Town/Hot Tub/Fire Pit
3 bedrooms, 6 beds, 1 bathroom
28 Aug – 2 Sept
4.92 out of 5 average rating, 12 reviews