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Search results; Over 1,000 homes in Chestertown

Top guest favourite
Chalet in Chestertown
The Roost, a lake front 4 season home
4 bedrooms, 7 beds, 3 private bathrooms
13–18 Sept
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4.98 out of 5 average rating, 65 reviews
Top guest favourite
Flat in Chestertown
Rustic Adirondack Studio Apartment
1 bedroom, 1 queen bed
4–9 Oct
5.0 out of 5 average rating, 120 reviews
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds
1–6 Aug
4.96 out of 5 average rating, 273 reviews
Top guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms, 3 beds
26–31 Aug
4.95 out of 5 average rating, 264 reviews
Guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
2 bedrooms
22–29 Aug
4.95 out of 5 average rating, 43 reviews
Guest favourite
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
3 bedrooms, 4 beds
2–7 Aug
4.93 out of 5 average rating, 41 reviews
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds
9–14 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds
23–28 Aug
5.0 out of 5 average rating, 58 reviews
Superhost
Cottage in Chestertown
Friends Lake Adirondack Cottage
3 bedrooms, 4 beds
18–23 Aug
4.85 out of 5 average rating, 40 reviews
Top guest favourite
Cabin in Chestertown
Posh Camp a Classic Adk Mtn. Cabin & Guide Srvc.
1 bedroom, 1 queen bed
14–19 Aug
4.99 out of 5 average rating, 89 reviews
Guest favourite
Home in Chestertown
Gorgeous 4BR Lakefront Friends Lake, NY | Dock
4 bedrooms, 6 beds
9–14 Oct
4.88 out of 5 average rating, 60 reviews
Guest favourite
Home in Chestertown
House in the Adirondacks, 15 min from Gore!
3 bedrooms, 5 beds
28 Aug – 2 Sept
4.93 out of 5 average rating, 42 reviews
Top guest favourite
Chalet in Chestertown
Chalet on Loon Lake (Gore Mt. 20 min.)
4 bedrooms, 5 beds
17–22 Oct
4.98 out of 5 average rating, 175 reviews
Superhost
Cabin in Chestertown
Quaint Adirondack Condo
1 bedroom, 3 beds
8–13 Sept
4.79 out of 5 average rating, 29 reviews
Top guest favourite
Home in Chestertown
Big Bear Lodge w/ Hot Tub and Sauna
2 bedrooms, 6 beds
6–11 Sept
4.93 out of 5 average rating, 76 reviews
Cottage in Chestertown
Private Dock & Beach! Lakefront, Fire Pit, Boats
2 bedrooms, 2 beds
30 Aug – 4 Sept
Guest favourite
Home in Chestertown
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
3 bedrooms, 5 beds
7–12 Sept
4.96 out of 5 average rating, 115 reviews
Guest favourite
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
3 bedrooms, 7 beds
22–27 Aug
4.83 out of 5 average rating, 6 reviews
Guest favourite
Barn in Chestertown
Adirondack Base Camp by Loon Lake and Gore Mt.!
2 bedrooms, 7 beds
6–11 Sept
4.95 out of 5 average rating, 103 reviews