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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
25–30 Aug
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4.96 out of 5 average rating, 277 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
Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds, 2 bathrooms
26–31 Aug
5.0 out of 5 average rating, 60 reviews
Cottage in Chestertown
Private Dock & Beach! Lakefront, Fire Pit, Boats
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 3 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
Cottage in Chestertown
Private Loon Lake property, cozy cabin on 3 Acres
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 56 reviews
Superhost
Cottage in Chestertown
Friends Lake Adirondack Cottage
3 bedrooms, 4 beds, 1 bathroom
25–30 Aug
4.85 out of 5 average rating, 41 reviews
Guest favourite
Cabin in Chestertown
Posh Camp a Classic Adk Mtn. Cabin & Guide Srvc.
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 90 reviews
Guest favourite
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
2 bedrooms, 2 bathrooms
22–29 Aug
4.96 out of 5 average rating, 45 reviews
Guest favourite
Home in Chestertown
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 115 reviews
Top guest favourite
Shared room in Wevertown
Custom Built 4 Person Bunk Room @LlamaHouseADK
1 bedroom, 2 bunk beds, 3 shared bathrooms
28 Aug – 2 Sept
4.89 out of 5 average rating, 131 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
Home in Chestertown
Enchanted Chestertown Getaway
3 bedrooms, 4 beds, 1.5 bathrooms
8–13 Sept
New place to stay
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
Guest favourite
Barn in Chestertown
Adirondack Base Camp by Loon Lake and Gore Mt.!
2 bedrooms, 7 beds, 1 bathroom
6–11 Sept
4.95 out of 5 average rating, 103 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, 131 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, 122 reviews
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4 bedrooms, 7 beds, 3 bathrooms
30 Aug – 4 Sept
4.94 out of 5 average rating, 17 reviews