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Search results; Over 1,000 homes in Chestertown

Guest favourite
Home in Chestertown
Adirondack 🏠 near Gore Mt, North Creek, Loon lake.
2 bedrooms, 6 beds, 2 private bathrooms
5–10 Jul
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4.92 out of 5 average rating, 120 reviews
Top guest favourite
Home in Chestertown
Adirondack Lake House
4.95 out of 5 average rating, 259 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
Top guest favourite
Home in Chestertown
The Hayes Homestead
5.0 out of 5 average rating, 55 reviews, 3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
4.96 out of 5 average rating, 267 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4.93 out of 5 average rating, 15 reviews, 4 bedrooms, 7 beds, 3 bathrooms
23–28 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
5–10 Jul
Guest favourite
Home in Chestertown
Waterfront Pond/Walk To Town/Hot Tub/Fire Pit
4.9 out of 5 average rating, 10 reviews, 3 bedrooms, 6 beds, 1 bathroom
5–10 Jul
Top guest favourite
Chalet in Chestertown
Chalet on Loon Lake (Gore Mt. 20 min.)
4.98 out of 5 average rating, 174 reviews, 4 bedrooms, 5 beds, 2 bathrooms
17–22 Oct
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
Cabin in Chestertown
Meadow House
4.88 out of 5 average rating, 161 reviews, 5 bedrooms, 9 beds, 3 bathrooms
11–16 Jul
Cabin in Chestertown
Lake Cabin Retreat
New place to stay, 3 bedrooms, 6 beds, 2 bathrooms
22–27 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
16–21 Oct
Home in Chestertown
Child-friendly 3BR Adirondacks | Fireplace
4.89 out of 5 average rating, 55 reviews, 3 bedrooms, 4 beds, 2 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Pottersville
Bring Your Dog | River Dock + Fire Table
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Top guest favourite
Chalet in Chestertown
The Roost, a lake front 4 season home
4.98 out of 5 average rating, 65 reviews, 4 bedrooms, 7 beds, 3 bathrooms
13–18 Sept
Superhost
Home in Chestertown
The Ramblewood. Family Friendly.
4.68 out of 5 average rating, 260 reviews, 6 bedrooms, 8 beds, 3 bathrooms
19–24 Jul
Guest favourite
Cabin in Chestertown
Cozy Adirondack Cabin w/ Fire Pit & Lake Access
4.9 out of 5 average rating, 39 reviews, 4 bedrooms, 8 beds, 2 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Chestertown
Cozy Adk Victorian! Ski, hike, hottub, relax!
4.97 out of 5 average rating, 66 reviews, 4 bedrooms, 7 beds, 3 bathrooms
9–14 Aug
Top guest favourite
Home in Brant Lake
Amazing Adirondack Lodge/Cabin-Crystal Lake
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 3 beds, 2 bathrooms
11–16 Jul