Search results; Over 1,000 homes in Chestertown

Chalet in Chestertown
Lake George Adirondack stye house
5 bedrooms, 8 beds, 2 private bathrooms
23–28 Aug
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4.8 out of 5 average rating, 198 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, 259 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, 173 reviews
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4 bedrooms, 7 beds, 3 bathrooms
23–28 Aug
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds, 2 bathrooms
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, 4 bathrooms
1–6 Aug
4.92 out of 5 average rating, 142 reviews
Home in Chestertown
Rustic Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
12–17 Jul
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
4.96 out of 5 average rating, 266 reviews
Guest favourite
Home in Chestertown
Gorgeous 4BR Lakefront Friends Lake, NY | Dock
4 bedrooms, 7 beds, 3.5 bathrooms
16–21 Oct
4.88 out of 5 average rating, 60 reviews
Guest favourite
Home in Chestertown
Chestertown Charm close to Gore Mt. Come ski!
3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
4.92 out of 5 average rating, 39 reviews
Guest favourite
Home in Chestertown
Waterfront Pond/Walk To Town/Hot Tub/Fire Pit
3 bedrooms, 6 beds, 1 bathroom
5–10 Jul
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Home in Chestertown
Cozy Adk Victorian! Ski, hike, hottub, relax!
4 bedrooms, 7 beds, 3 bathrooms
9–14 Aug
4.97 out of 5 average rating, 66 reviews
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
28 Jul – 2 Aug
New place to stay
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
3 bedrooms, 7 beds, 3 bathrooms
5–10 Jul
Home in Chestertown
Quiet Chestertown Escape | Nearby Gore & Lakes
3 bedrooms, 4 beds, 2 bathrooms
6–11 Jul
Superhost
Home in Chestertown
Sleeps 16 Heated Pool Firepit Minutes Lake George
6 bedrooms, 10 beds, 3 bathrooms
23–28 Aug
4.69 out of 5 average rating, 78 reviews
Top guest favourite
Home in Pottersville
Bring Your Dog | River Dock + Fire Table
2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 10 reviews
Cabin in Chestertown
Newly built Adirondack Home in Lake George Area!
3 bedrooms, 5 beds, 2.5 bathrooms
16–21 Aug
Top guest favourite
Cabin in Chestertown
Posh Camp a Classic Adk Mtn. Cabin & Guide Srvc.
1 bedroom, 1 queen bed, 1 bathroom
27 Jul – 1 Aug
4.99 out of 5 average rating, 85 reviews