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Search results; Over 1,000 homes in Chestertown

Top guest favourite
Chalet in Chestertown
The Roost, a lake front 4 season home
4 bedrooms, 7 beds, 3 private bathrooms
13–18 Sept
,
4.98 out of 5 average rating, 65 reviews
Top guest favourite
Flat in Chestertown
Rustic Adirondack Studio Apartment
5.0 out of 5 average rating, 120 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct
Top guest favourite
Home in Chestertown
Adirondack Lake House
4.95 out of 5 average rating, 264 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, 273 reviews, 2 bedrooms, 3 beds, 1 bathroom
1–6 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
2–7 Aug
Guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
4.95 out of 5 average rating, 43 reviews, 2 bedrooms, 2 bathrooms
22–29 Aug
Cabin in Chestertown
Lake Cabin Retreat
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
Top guest favourite
Home in Chestertown
The Hayes Homestead
5.0 out of 5 average rating, 58 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
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
Cabin in Chestertown
Posh Camp a Classic Adk Mtn. Cabin & Guide Srvc.
4.99 out of 5 average rating, 89 reviews, 1 bedroom, 1 bed, 1 bathroom
14–19 Aug
Cottage in Chestertown
Private Dock & Beach! Lakefront, Fire Pit, Boats
2 bedrooms, 2 beds, 1 bathroom
5–10 Aug
Guest favourite
Home in Chestertown
Gorgeous 4BR Lakefront Friends Lake, NY | Dock
4.88 out of 5 average rating, 60 reviews, 4 bedrooms, 6 beds, 3.5 bathrooms
9–14 Oct
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
Cabin in Chestertown
Quaint Adirondack Condo
4.79 out of 5 average rating, 29 reviews, 1 bedroom, 3 beds, 1 bathroom
8–13 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
Big Bear Lodge w/ Hot Tub and Sauna
4.93 out of 5 average rating, 76 reviews, 2 bedrooms, 6 beds, 1.5 bathrooms
6–11 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
Guest favourite
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
4.8 out of 5 average rating, 5 reviews, 3 bedrooms, 7 beds, 3 bathrooms
22–27 Aug
Superhost
Home in Chestertown
The Ramblewood. Family Friendly.
4.68 out of 5 average rating, 260 reviews, 6 bedrooms, 8 beds, 3 bathrooms
16–21 Aug