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Search results; Over 1,000 homes in Chestertown

Top guest favourite
Chalet in Chestertown
Chalet on Loon Lake (Gore Mt. 20 min.)
4 bedrooms, 5 beds, 2 private bathrooms
18–23 Oct
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4.98 out of 5 average rating, 175 reviews
Top guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
4.96 out of 5 average rating, 267 reviews
Cottage in Chestertown
Private Dock & Beach! Lakefront, Fire Pit, Boats
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 bathroom
25–30 Aug
4.96 out of 5 average rating, 275 reviews
Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds, 2 bathrooms
26–31 Aug
5.0 out of 5 average rating, 59 reviews
Guest favourite
Cabin in Town of Johnsburg
2 bdrm ADK cabin 10 mins to GORE MTN
2 bedrooms, 3 beds, 1 bathroom
22–27 Sept
4.97 out of 5 average rating, 162 reviews
Guest favourite
Cabin in Chestertown
Posh Camp a Classic Adk Mtn. Cabin & Guide Srvc.
1 bedroom, 1 queen bed, 1 bathroom
15–20 Aug
4.98 out of 5 average rating, 90 reviews
Guest favourite
Cottage in Chestertown
Private Loon Lake property, cozy cabin on 3 Acres
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 55 reviews
Top guest favourite
Cabin in Warrensburg
Bearpine Cottage
2 bedrooms, 5 beds, 1 bathroom
2–7 Sept
4.97 out of 5 average rating, 131 reviews
Guest favourite
Cabin in Chestertown
Meadow House
5 bedrooms, 9 beds, 3 bathrooms
23–28 Aug
4.88 out of 5 average rating, 166 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
Guest favourite
Home in Chestertown
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 115 reviews
Superhost
Cabin in Chestertown
Quaint Adirondack Condo
1 bedroom, 3 beds, 1 bathroom
13–18 Sept
4.73 out of 5 average rating, 30 reviews
Guest favourite
Home in Adirondack
SH House
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.96 out of 5 average rating, 244 reviews
Home in Chestertown
Enchanted Chestertown Getaway
3 bedrooms, 4 beds, 1.5 bathrooms
8–13 Sept
New place to stay
Top guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
2 bedrooms, 2 bathrooms
22–29 Aug
4.96 out of 5 average rating, 45 reviews
Top guest favourite
Guest suite in Pottersville
Private Spacious Suite near Lakes, Peaks & WOL-BI
2 beds, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 172 reviews
Top guest favourite
Home in Chestertown
Pond Farmhouse: Private Hot Tub, Fire Pit, Town
3 bedrooms, 6 beds, 1 bathroom
5–10 Sept
4.93 out of 5 average rating, 15 reviews
Top guest favourite
Home in Warrensburg
Lake George | Hot Tub | Firepit | Schroon Lake
2 bedrooms, 4 beds, 1.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 165 reviews