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Search results; Over 1,000 homes in Chestertown

Descriptions are based on details hosts provide
Superhost
Cottage in Chestertown
Friends Lake Adirondack Cottage
3 bedrooms, 4 beds, 1 shared bathroom
18–23 Aug
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4.85 out of 5 average rating, 39 reviews
Top guest favourite
Home in Chestertown
Wooded retreat with lake access and kayaks
4.95 out of 5 average rating, 261 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
4.96 out of 5 average rating, 271 reviews, 2 bedrooms, 3 beds, 1 bathroom
20–25 Jul
Guest favourite
Barn in Chestertown
Adirondack Base Camp by Loon Lake and Gore Mt.!
4.95 out of 5 average rating, 103 reviews, 2 bedrooms, 7 beds, 1 bathroom
6–11 Sept
Guest favourite
Cottage in Chestertown
Private Loon Lake property, cozy cabin on 3 Acres
4.92 out of 5 average rating, 53 reviews, 2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
Guest favourite
Home in Chestertown
Lake views and a dock on Loon Lake
4.93 out of 5 average rating, 42 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
28 Aug – 2 Sept
Top guest favourite
Flat in Chestertown
Rustic Adirondack Studio Apartment
5.0 out of 5 average rating, 120 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct
Top guest favourite
Home in Chestertown
Adirondack Victorian with a hot tub
4.97 out of 5 average rating, 68 reviews, 4 bedrooms, 7 beds, 3 bathrooms
27 Jul – 1 Aug
Guest favourite
Cabin in Brant Lake
Log cabin with river access and canoe
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 5 beds, 2 bathrooms
18–23 Jul
Top guest favourite
Home in Pottersville
Bring Your Dog | River Dock + Fire Table
5.0 out of 5 average rating, 11 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Top guest favourite
Home in Adirondack
Adirondack Owl's Nest Guest House
5.0 out of 5 average rating, 182 reviews, 4 bedrooms, 4 beds, 2 bathrooms
24–29 Aug
Guest favourite
Home in Chestertown
Hot tub, arcade, and wraparound decks
4.94 out of 5 average rating, 97 reviews, 3 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Home in Warrensburg
River House
4.97 out of 5 average rating, 63 reviews, 3 bedrooms, 8 beds, 2.5 bathrooms
11–16 Sept
Guest favourite
Home in Chestertown
Adirondack pine retreat with a hot tub
4.85 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 1 bathroom
2–7 Aug
Top guest favourite
Chalet in Chestertown
Chalet on Loon Lake (Gore Mt. 20 min.)
4.98 out of 5 average rating, 175 reviews, 4 bedrooms, 5 beds, 2 bathrooms
17–22 Oct
Top guest favourite
Guest house in Brant Lake
Patio overlooking Brant Lake with sauna
4.98 out of 5 average rating, 106 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Warrensburg
Lake George | Hot Tub | Firepit | Schroon Lake
4.98 out of 5 average rating, 160 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
23–28 Aug
Guest favourite
Townhouse in Chestertown
Gas fireplace and lake access in Adirondacks
4.96 out of 5 average rating, 27 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
22–27 Aug
Top guest favourite
Home in Chestertown
Adirondack retreat near Lake George
5.0 out of 5 average rating, 56 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug