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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
10–15 Sept
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4.98 out of 5 average rating, 175 reviews
Guest favourite
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.96 out of 5 average rating, 272 reviews
Guest favourite
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Chestertown
House in the Adirondacks, 15 min from Gore!
3 bedrooms, 5 beds, 2.5 bathrooms
9–14 Sept
4.93 out of 5 average rating, 43 reviews
Top guest favourite
Cabin in Chestertown
Pine Tree Cove on Friends Lake
4 bedrooms, 12 beds, 4 bathrooms
10–15 Sept
4.98 out of 5 average rating, 83 reviews
Guest favourite
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Sept
4.91 out of 5 average rating, 46 reviews
Top guest favourite
Home in Chestertown
Shore fun waterfront lake house Close to Gore Mtn.
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
4.9 out of 5 average rating, 20 reviews
Guest favourite
Home in Chestertown
Family friendly Adirondack dream, no cleaning fee!
3 bedrooms, 5 beds, 2 bathrooms
29 Sept – 4 Oct
4.93 out of 5 average rating, 100 reviews
Top guest favourite
Home in Adirondack
Adirondack Owl's Nest Guest House
4 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 189 reviews
Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 61 reviews
Guest favourite
Cabin in Chestertown
Meadow House
5 bedrooms, 9 beds, 3 bathrooms
18–23 Sept
4.88 out of 5 average rating, 167 reviews
Guest favourite
Barn in Chestertown
Adirondack Base Camp by Loon Lake and Gore Mt.!
2 bedrooms, 7 beds, 1 bathroom
12–17 Oct
4.95 out of 5 average rating, 103 reviews
Home in Chestertown
Enchanted Chestertown Getaway
3 bedrooms, 4 beds, 1.5 bathrooms
28 Oct – 2 Nov
New place to stay
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.96 out of 5 average rating, 280 reviews
Guest favourite
Cottage in Chestertown
Private Loon Lake property, cozy cabin on 3 Acres
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.93 out of 5 average rating, 57 reviews
Top guest favourite
Flat in Chestertown
Rustic Adirondack Studio Apartment
1 bedroom, 1 queen bed, 1 bathroom
5–10 Oct
5.0 out of 5 average rating, 123 reviews
Home in Chestertown
Year-Round Loon Lake Retreat: Ski, Hike, Explore!
3 bedrooms, 6 beds, 3 bathrooms
14–19 Sept
Top guest favourite
Home in Chestertown
The Stone Lodge on Blythewood Island on Loon Lake
4 bedrooms, 6 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 184 reviews