filters

Search results; Over 1,000 homes in Chestertown

Top guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms, 3 beds, 1 private bathroom
9–14 Aug
,
4.95 out of 5 average rating, 260 reviews
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
4.96 out of 5 average rating, 269 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
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
Home in Chestertown
The Hayes Homestead
5.0 out of 5 average rating, 56 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Guest favourite
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
4.92 out of 5 average rating, 39 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
Top guest favourite
Home in Chestertown
Cozy Adk Victorian! Ski, hike, hottub, relax!
4.97 out of 5 average rating, 68 reviews, 4 bedrooms, 7 beds, 3 bathrooms
27 Jul – 1 Aug
Cabin in Chestertown
Lake Cabin Retreat
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 6 beds, 2 bathrooms
22–27 Aug
Guest favourite
Home in Chestertown
Adirondack 🏠 near Gore Mt, North Creek, Loon lake.
4.92 out of 5 average rating, 120 reviews, 2 bedrooms, 6 beds, 2 bathrooms
1–6 Aug
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4.94 out of 5 average rating, 16 reviews, 4 bedrooms, 7 beds, 3 bathrooms
23–28 Aug
Top guest favourite
Home in Chestertown
Adirondack Home 15 minutes to Gore and Lake George
5.0 out of 5 average rating, 33 reviews, 4 bedrooms, 11 beds, 2.5 bathrooms
25–30 Jul
Superhost
Home in Chestertown
Child-friendly 3BR Adirondacks | Fireplace
4.89 out of 5 average rating, 55 reviews, 3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Chestertown
Gorgeous 4BR Lakefront Friends Lake, NY | Dock
4.88 out of 5 average rating, 60 reviews, 4 bedrooms, 6 beds, 3.5 bathrooms
16–21 Oct
Top guest favourite
Chalet in Chestertown
The Roost, a lake front 4 season home
4.98 out of 5 average rating, 65 reviews, 4 bedrooms, 7 beds, 3 bathrooms
13–18 Sept
Top guest favourite
Home in Chestertown
Waterfront Pond/Walk To Town/Hot Tub/Fire Pit
4.92 out of 5 average rating, 12 reviews, 3 bedrooms, 6 beds, 1 bathroom
3–8 Aug
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
Superhost
Home in Chestertown
The Ramblewood. Family Friendly.
4.68 out of 5 average rating, 260 reviews, 6 bedrooms, 8 beds, 3 bathrooms
19–24 Jul
Guest favourite
Home in Chestertown
Rita's Place
5.0 out of 5 average rating, 23 reviews, 3 bedrooms, 3 beds, 2 bathrooms
9–14 Jul
Cabin in Chestertown
Meadow House
4.88 out of 5 average rating, 161 reviews, 5 bedrooms, 9 beds, 3 bathrooms
11–16 Jul
Guest favourite
Cabin in Brant Lake
ForeverWild Cabin- Close to LG, Firepit, Pavilion
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 5 beds, 2 bathrooms
18–23 Jul