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Search results; Over 1,000 homes in Chestertown

Guest favourite
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
3 bedrooms, 4 beds, 2.5 private bathrooms
1–6 Sept
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4.91 out of 5 average rating, 45 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, 269 reviews
Cottage in Chestertown
Private Dock & Beach! Lakefront, Fire Pit, Boats
2 bedrooms, 2 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 277 reviews
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 5 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, 6 reviews
Top guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
2 bedrooms, 2 bathrooms
3–8 Sept
4.96 out of 5 average rating, 45 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, 60 reviews
Top guest favourite
Chalet in Chestertown
Chalet on Loon Lake (Gore Mt. 20 min.)
4 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
4.98 out of 5 average rating, 175 reviews
Superhost
Cottage in Chestertown
Friends Lake Adirondack Cottage
3 bedrooms, 4 beds, 1 bathroom
1–6 Sept
4.85 out of 5 average rating, 41 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
Cabin in Warrensburg
Bearpine Cottage
2 bedrooms, 5 beds, 1 bathroom
9–14 Nov
4.97 out of 5 average rating, 132 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, 163 reviews
Superhost
Home in Chestertown
The Ramblewood. Family Friendly.
6 bedrooms, 8 beds, 3 bathrooms
7–12 Sept
4.69 out of 5 average rating, 262 reviews
Guest favourite
Cabin in Chestertown
Meadow House
5 bedrooms, 9 beds, 3 bathrooms
1–6 Sept
4.88 out of 5 average rating, 167 reviews
Superhost
Home in Chestertown
Child-friendly 3BR Adirondacks | Fireplace
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.89 out of 5 average rating, 57 reviews
Top guest favourite
Shared room in Wevertown
Custom Built 4 Person Bunk Room @LlamaHouseADK
1 bedroom, 2 bunk beds, 3 shared bathrooms
7–12 Sept
4.89 out of 5 average rating, 131 reviews
Top guest favourite
Home in Adirondack
SH House
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
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
8–13 Sept
4.93 out of 5 average rating, 43 reviews