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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
13–18 Sept
4.96 out of 5 average rating, 272 reviews
Guest favourite
Cottage in Chestertown
Private Loon Lake property, cozy cabin on 3 Acres
2 bedrooms, 2 beds
20–25 Sept
4.93 out of 5 average rating, 57 reviews
Top guest favourite
Home in Chestertown
Shore fun waterfront lake house Close to Gore Mtn.
3 bedrooms, 4 beds
11–16 Sept
4.9 out of 5 average rating, 20 reviews
Guest favourite
Home in Chestertown
Mimi’s by the lake
6 bedrooms, 9 beds
27 Sept – 2 Oct
4.92 out of 5 average rating, 26 reviews
Top guest favourite
Home in Chestertown
The Stone Lodge on Blythewood Island on Loon Lake
4 bedrooms, 6 beds
27 Sept – 2 Oct
4.94 out of 5 average rating, 185 reviews
Guest favourite
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds
10–15 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Chestertown
Blue Bay Retreat - Loon Lake Lakefront w/ Hot Tub
4 bedrooms, 9 beds
19–24 Oct
5.0 out of 5 average rating, 77 reviews
Guest favourite
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds
13–18 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 61 reviews
Top guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
2 bedrooms
13–18 Sept
4.96 out of 5 average rating, 46 reviews
Cottage in Chestertown
Private Dock & Beach! Lakefront, Fire Pit, Boats
2 bedrooms, 2 beds
14–19 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Chestertown
Rustic Adirondack Studio Apartment
1 bedroom, 1 queen bed
5–10 Oct
5.0 out of 5 average rating, 123 reviews
Guest favourite
Home in Chestertown
House in the Adirondacks, 15 min from Gore!
3 bedrooms, 5 beds
11–16 Sept
4.91 out of 5 average rating, 44 reviews
Top guest favourite
Home in Chestertown
Modern ADK House-Lake and Mountain View-Sleeps 16
4 bedrooms, 11 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 39 reviews
Home in Chestertown
Enchanted Chestertown Getaway
3 bedrooms, 4 beds
28 Oct – 2 Nov
New place to stay
Superhost
Home in Chestertown
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
3 bedrooms, 5 beds
13–18 Sept
4.93 out of 5 average rating, 116 reviews
Top guest favourite
Home in Adirondack
Adirondack Owl's Nest Guest House
4 bedrooms, 4 beds
11–16 Sept
5.0 out of 5 average rating, 189 reviews
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4 bedrooms, 7 beds
13–18 Sept
4.94 out of 5 average rating, 18 reviews