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Search results; Over 1,000 homes in Chestertown

Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 private bathroom
24–29 Aug
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4.96 out of 5 average rating, 273 reviews
Top guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
4.95 out of 5 average rating, 265 reviews
Top guest favourite
Flat in Chestertown
Rustic Adirondack Studio Apartment
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 121 reviews
Home in Chestertown
Enchanted Chestertown Getaway
3 bedrooms, 4 beds, WC
8–13 Sept
New place to stay
Guest favourite
Townhouse in Chestertown
Secluded and Cozy Townhome at Tripp Lake
3 bedrooms, 3 beds, 2.5 bathrooms
29 Aug – 3 Sept
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 58 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
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
2 bedrooms, 2 bathrooms
29 Aug – 5 Sept
4.96 out of 5 average rating, 45 reviews
Superhost
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Aug
4.91 out of 5 average rating, 43 reviews
Cottage in Chestertown
Private Dock & Beach! Lakefront, Fire Pit, Boats
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
Top guest favourite
Cabin in Chestertown
Posh Camp a Classic Adk Mtn. Cabin & Guide Srvc.
1 bedroom, 1 queen bed, 1 bathroom
14–19 Aug
4.99 out of 5 average rating, 89 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, 42 reviews
Superhost
Cabin in Chestertown
Quaint Adirondack Condo
1 bedroom, 3 beds, 1 bathroom
13–18 Sept
4.79 out of 5 average rating, 29 reviews
Guest favourite
Home in Chestertown
Family friendly Adirondack dream, no cleaning fee!
3 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
4.94 out of 5 average rating, 97 reviews
Guest favourite
Home in Chestertown
Gorgeous 4BR Lakefront Friends Lake, NY | Dock
4 bedrooms, 6 beds, 3.5 bathrooms
13–18 Oct
4.88 out of 5 average rating, 60 reviews
Top guest favourite
Home in Chestertown
Blue Bay Retreat - Loon Lake Lakefront w/ Hot Tub
4 bedrooms, 9 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 72 reviews
Guest favourite
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
3 bedrooms, 7 beds, 3 bathrooms
22–27 Aug
4.86 out of 5 average rating, 7 reviews
Superhost
Home in Chestertown
The Ramblewood. Family Friendly.
6 bedrooms, 8 beds, 3 bathrooms
16–21 Aug
4.68 out of 5 average rating, 260 reviews
Top guest favourite
Guest house in Brant Lake
Arrowhead @ Brant Lake
1 bedroom, 1 king bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 110 reviews