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Search results; Over 1,000 homes in Chestertown

Top guest favourite
Chalet in Chestertown
Chalet on Loon Lake (Gore Mt. 20 min.)
4 bedrooms, 5 beds, 2 private bathrooms
17–22 Oct
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4.98 out of 5 average rating, 175 reviews
Top guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms, 3 beds, 1 bathroom
26–31 Aug
4.95 out of 5 average rating, 262 reviews
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 bathroom
21–26 Jul
4.96 out of 5 average rating, 273 reviews
Top guest favourite
Flat in Chestertown
Rustic Adirondack Studio Apartment
1 bedroom, 1 queen bed, 1 bathroom
30 Jul – 4 Aug
5.0 out of 5 average rating, 120 reviews
Guest favourite
Cottage in Chestertown
Private Loon Lake property, cozy cabin on 3 Acres
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 54 reviews
Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 57 reviews
Guest favourite
Holiday home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
2 bedrooms, 2 bathrooms
22–29 Aug
4.95 out of 5 average rating, 43 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
Shared room in Wevertown
Custom Built 4 Person Bunk Room @LlamaHouseADK
1 bedroom, 2 bunk beds, 3 shared bathrooms
23–28 Jul
4.88 out of 5 average rating, 127 reviews
Superhost
Home in Chestertown
The Ramblewood. Family Friendly.
6 bedrooms, 8 beds, 3 bathrooms
22–27 Jul
4.68 out of 5 average rating, 260 reviews
Superhost
Cabin in Chestertown
Quaint Adirondack Condo
1 bedroom, 3 beds, 1 bathroom
8–13 Sept
4.79 out of 5 average rating, 29 reviews
Guest favourite
Home in Chestertown
Gorgeous 4BR Lakefront Friends Lake, NY | Dock
4 bedrooms, 6 beds, 3.5 bathrooms
16–21 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, 2.5 bathrooms
28 Aug – 2 Sept
4.93 out of 5 average rating, 42 reviews
Top guest favourite
Cabin in Chestertown
Posh Camp a Classic Adk Mtn. Cabin & Guide Srvc.
1 bedroom, 1 queen bed, 1 bathroom
14–19 Aug
4.99 out of 5 average rating, 88 reviews
Guest favourite
Home in Chestertown
Family friendly Adirondack dream, no cleaning fee!
3 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
4.94 out of 5 average rating, 97 reviews
Guest favourite
Cabin in Brant Lake
ForeverWild Cabin- Close to LG, Firepit, Pavilion
3 bedrooms, 5 beds, 2 bathrooms
22–27 Jul
5.0 out of 5 average rating, 22 reviews
Guest favourite
Room in Wevertown
Handcrafted Room 25 min from Lake George
3 beds, 3 bathrooms
25–30 Jul
4.97 out of 5 average rating, 149 reviews
Superhost
Tent in Warrensburg
Lonetree Glamping campsite 2
1 bedroom, 2 beds, 1 bathroom
26–31 Jul
Top guest favourite
Home in Chestertown
Waterfront Pond/Walk To Town/Hot Tub/Fire Pit
3 bedrooms, 6 beds, 1 bathroom
28 Aug – 2 Sept
4.92 out of 5 average rating, 12 reviews