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Search results; Over 1,000 homes in Chestertown

Guest favourite
Cabin in Chestertown
Adirondack Private Lakefront Knotty Pine Cabin
3 bedrooms, 5 beds, 2 private bathrooms
14–19 Sept
,
4.81 out of 5 average rating, 93 reviews
Top guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms, 3 beds
9–14 Aug
4.95 out of 5 average rating, 259 reviews
Top guest favourite
Chalet in Chestertown
Chalet on Loon Lake (Gore Mt. 20 min.)
4 bedrooms, 5 beds
17–22 Oct
4.98 out of 5 average rating, 174 reviews
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4 bedrooms, 7 beds
23–28 Aug
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds
25–30 Jul
5.0 out of 5 average rating, 54 reviews
Home in Chestertown
Eagles Nest at Loon Lake near Gore Mountain
7 bedrooms, 16 beds
1–6 Aug
4.92 out of 5 average rating, 142 reviews
Home in Chestertown
Child-friendly 3BR Adirondacks | Fireplace
3 bedrooms, 4 beds
29 Aug – 3 Sept
4.89 out of 5 average rating, 55 reviews
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds
5–10 Jul
4.96 out of 5 average rating, 266 reviews
Guest favourite
Home in Chestertown
Chestertown Charm close to Gore Mt. Come ski!
3 bedrooms, 4 beds
5–10 Jul
4.92 out of 5 average rating, 39 reviews
Top guest favourite
Home in Chestertown
Cozy Adk Victorian! Ski, hike, hottub, relax!
4 bedrooms, 7 beds
9–14 Aug
4.97 out of 5 average rating, 66 reviews
Home in Chestertown
Quiet Chestertown Escape | Nearby Gore & Lakes
3 bedrooms, 4 beds
6–11 Jul
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
3 bedrooms, 7 beds
5–10 Jul
Guest favourite
Home in Chestertown
Gorgeous 4BR Lakefront Friends Lake, NY | Dock
4 bedrooms, 7 beds
16–21 Oct
4.88 out of 5 average rating, 60 reviews
Guest favourite
Home in Chestertown
Waterfront Pond/Walk To Town/Hot Tub/Fire Pit
3 bedrooms, 6 beds
5–10 Jul
4.9 out of 5 average rating, 10 reviews
Cabin in Chestertown
Newly built Adirondack Home in Lake George Area!
3 bedrooms, 5 beds
16–21 Aug
Superhost
Home in Chestertown
Sleeps 16 Heated Pool Firepit Minutes Lake George
6 bedrooms, 10 beds
23–28 Aug
4.69 out of 5 average rating, 78 reviews
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds
28 Jul – 2 Aug
New place to stay
Guest favourite
Cabin in Chestertown
Sleeps 10 | Adirondack Summer Escapes & Adventures
3 bedrooms, 6 beds
15–20 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Pottersville
Bring Your Dog | River Dock + Fire Table
2 bedrooms, 2 beds
6–11 Jul
5.0 out of 5 average rating, 10 reviews