filters

Search results; Over 1,000 homes in Chestertown

Guest favourite
Home in Chestertown
Adirondack 🏠 near Gore Mt, North Creek, Loon lake.
2 bedrooms, 6 beds, 2 private bathrooms
1–6 Aug
,
4.92 out of 5 average rating, 120 reviews
Top guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
4.95 out of 5 average rating, 259 reviews
Top guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms, 4 beds, 2 bathrooms
6–11 Jul
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Chalet in Chestertown
Chalet on Loon Lake (Gore Mt. 20 min.)
4 bedrooms, 5 beds, 2 bathrooms
17–22 Oct
4.98 out of 5 average rating, 175 reviews
Top guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4 bedrooms, 7 beds, 3 bathrooms
23–28 Aug
4.94 out of 5 average rating, 16 reviews
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms, 6 beds, 2 bathrooms
22–27 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
4.96 out of 5 average rating, 268 reviews
Guest favourite
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
3 bedrooms, 4 beds, 2.5 bathrooms
18–23 Jul
4.92 out of 5 average rating, 39 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
Home in Chestertown
Child-friendly 3BR Adirondacks | Fireplace
3 bedrooms, 4 beds, 2 bathrooms
29 Aug – 3 Sept
4.89 out of 5 average rating, 55 reviews
Top guest favourite
Home in Chestertown
Cozy Adk Victorian! Ski, hike, hottub, relax!
4 bedrooms, 7 beds, 3 bathrooms
27 Jul – 1 Aug
4.97 out of 5 average rating, 67 reviews
Top guest favourite
Home in Chestertown
Adirondack Home 15 minutes to Gore and Lake George
4 bedrooms, 11 beds, 2.5 bathrooms
25–30 Jul
5.0 out of 5 average rating, 33 reviews
Home in Chestertown
Quiet Chestertown Escape | Nearby Gore & Lakes
3 bedrooms, 4 beds, 2 bathrooms
18–23 Jul
Top guest favourite
Home in Chestertown
Waterfront Pond/Walk To Town/Hot Tub/Fire Pit
3 bedrooms, 6 beds, 1 bathroom
3–8 Aug
4.92 out of 5 average rating, 12 reviews
Superhost
Home in Chestertown
The Ramblewood. Family Friendly.
6 bedrooms, 8 beds, 3 bathrooms
19–24 Jul
4.68 out of 5 average rating, 260 reviews
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
4 bedrooms, 5 beds, 2 bathrooms
9–14 Aug
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
3 bedrooms, 7 beds, 3 bathrooms
26–31 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Brant Lake
Amazing Adirondack Lodge/Cabin-Crystal Lake
3 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
5.0 out of 5 average rating, 21 reviews
Guest favourite
Home in Chestertown
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
3 bedrooms, 5 beds, 2 bathrooms
17–24 Aug
4.96 out of 5 average rating, 113 reviews