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Search results; Over 1,000 homes in Chestertown

Top guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms, 3 beds, 1 private bathroom
9–14 Aug
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4.95 out of 5 average rating, 259 reviews
Top guest favourite
Flat in Chestertown
Rustic Adirondack Studio Apartment
5.0 out of 5 average rating, 120 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
4.96 out of 5 average rating, 269 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Guest favourite
Cottage in Chestertown
Private Loon Lake property, cozy cabin on 3 Acres
4.92 out of 5 average rating, 53 reviews, 2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
Guest favourite
Barn in Chestertown
Adirondack Base Camp by Loon Lake and Gore Mt.!
4.95 out of 5 average rating, 103 reviews, 2 bedrooms, 7 beds, 1 bathroom
6–11 Sept
Top guest favourite
Home in Chestertown
Cozy Adk Victorian! Ski, hike, hottub, relax!
4.97 out of 5 average rating, 68 reviews, 4 bedrooms, 7 beds, 3 bathrooms
27 Jul – 1 Aug
Top guest favourite
Cabin in Warrensburg
Bearpine Cottage
4.97 out of 5 average rating, 123 reviews, 2 bedrooms, 5 beds, 1 bathroom
11–16 Aug
Top guest favourite
Home in Adirondack
Adirondack Owl's Nest Guest House
5.0 out of 5 average rating, 181 reviews, 4 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
4.75 out of 5 average rating, 4 reviews, 3 bedrooms, 7 beds, 3 bathrooms
26–31 Jul
Top guest favourite
Home in Warrensburg
River House
4.97 out of 5 average rating, 63 reviews, 3 bedrooms, 8 beds, 2.5 bathrooms
31 Aug – 5 Sept
Guest favourite
Cabin in Brant Lake
ForeverWild Cabin- Close to LG, Firepit, Pavilion
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 5 beds, 2 bathrooms
18–23 Jul
Top guest favourite
Home in Chestertown
The Hayes Homestead
5.0 out of 5 average rating, 56 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Guest favourite
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
4.92 out of 5 average rating, 39 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
18–23 Jul
Cabin in Chestertown
Lake Cabin Retreat
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 6 beds, 2 bathrooms
22–27 Aug
Top guest favourite
Guest house in Brant Lake
Arrowhead @ Brant Lake
4.98 out of 5 average rating, 106 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Home in Chestertown
Family friendly Adirondack dream, no cleaning fee!
4.94 out of 5 average rating, 97 reviews, 3 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Home in Pottersville
Bring Your Dog | River Dock + Fire Table
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Top guest favourite
Home in Warrensburg
Lake George | Hot Tub | Firepit | Schroon Lake
4.98 out of 5 average rating, 158 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
9–14 Aug
Guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
4.95 out of 5 average rating, 42 reviews, 2 bedrooms, 2 bathrooms
22–29 Aug