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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
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4.98 out of 5 average rating, 66 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
Guest favourite
Cabin in Chestertown
Posh Camp a Classic Adk Mtn. Cabin & Guide Srvc.
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 90 reviews
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
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
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
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
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
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
Home in Chestertown
Enchanted Chestertown Getaway
3 bedrooms, 4 beds, 1.5 bathrooms
8–13 Sept
New place to stay
Superhost
Home in Chestertown
Spacious Colonial Near Lake George Heated Pool
6 bedrooms, 10 beds, 3 bathrooms
23–28 Aug
4.69 out of 5 average rating, 80 reviews
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
Cabin in Chestertown
All-Season Family Retreat w/ Dock on Loon Lake!
3 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
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
Guest favourite
Home in Chestertown
House in the Adirondacks, 15 min from Gore!
3 bedrooms, 5 beds, 2.5 bathrooms
28 Aug – 2 Sept
4.93 out of 5 average rating, 43 reviews
Superhost
Home in Chestertown
Child-friendly 3BR Adirondacks | Fireplace
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.89 out of 5 average rating, 57 reviews