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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
Home in Chestertown
Adirondack Lake House
2 bedrooms, 3 beds
9–14 Aug
4.95 out of 5 average rating, 261 reviews
Top guest favourite
Flat in Chestertown
Rustic Adirondack Studio Apartment
1 bedroom, 1 queen bed
30 Aug – 4 Sept
5.0 out of 5 average rating, 120 reviews
Guest favourite
Barn in Chestertown
Adirondack Base Camp by Loon Lake and Gore Mt.!
2 bedrooms, 7 beds
17–22 Aug
4.95 out of 5 average rating, 103 reviews
Guest favourite
Cottage in Chestertown
Private Loon Lake property, cozy cabin on 3 Acres
2 bedrooms, 2 beds
7–12 Sept
4.92 out of 5 average rating, 53 reviews
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds
12–17 Jul
4.96 out of 5 average rating, 270 reviews
Top guest favourite
Home in Chestertown
Cozy Adk Victorian! Ski, hike, hottub, relax!
4 bedrooms, 7 beds
27 Jul – 1 Aug
4.97 out of 5 average rating, 68 reviews
Top guest favourite
Home in Warrensburg
River House
3 bedrooms, 8 beds
31 Aug – 5 Sept
4.97 out of 5 average rating, 63 reviews
Guest favourite
Cabin in Brant Lake
ForeverWild Cabin- Close to LG, Firepit, Pavilion
3 bedrooms, 5 beds
18–23 Jul
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Cabin in Warrensburg
Bearpine Cottage
2 bedrooms, 5 beds
11–16 Aug
4.97 out of 5 average rating, 123 reviews
Superhost
Home in Chestertown
Forest Lake Haven Main House
3 bedrooms, 5 beds
29 Jul – 4 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Pottersville
Bring Your Dog | River Dock + Fire Table
2 bedrooms, 2 beds
26–31 Jul
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Adirondack
Adirondack Owl's Nest Guest House
4 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 181 reviews
Guest favourite
Home in Chestertown
Shore fun waterfront lake house Close to Gore Mtn.
3 bedrooms, 4 beds
5–10 Sept
4.83 out of 5 average rating, 12 reviews
Cabin in Chestertown
Four Season Adirondack Cabin & Private Beach
2 bedrooms, 5 beds
7–12 Aug
4.76 out of 5 average rating, 46 reviews
Guest favourite
Home in Chestertown
Family friendly Adirondack dream, no cleaning fee!
3 bedrooms, 5 beds
8–13 Sept
4.94 out of 5 average rating, 97 reviews
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4 bedrooms, 7 beds
23–28 Aug
4.94 out of 5 average rating, 16 reviews
Guest favourite
Home in Pottersville
The Schoolhouse
2 bedrooms, 3 beds
12–17 Jul
4.93 out of 5 average rating, 15 reviews
Guest favourite
Home in Chestertown
House in the Adirondacks, 15 min from Gore!
3 bedrooms, 5 beds
22–27 Aug
4.93 out of 5 average rating, 42 reviews