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
,
4.98 out of 5 average rating, 65 reviews
Top guest favourite
Home in Chestertown
Adirondack Lake House
Kayak
9–14 Aug
4.95 out of 5 average rating, 261 reviews
Top guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
3 beds
20–25 Jul
4.96 out of 5 average rating, 271 reviews
Top guest favourite
Home in Chestertown
Cozy Adk Victorian! Ski, hike, hottub, relax!
7 beds
27 Jul – 1 Aug
4.97 out of 5 average rating, 68 reviews
Guest favourite
Home in Chestertown
Family friendly Adirondack dream, no cleaning fee!
5 beds
8–13 Sept
4.94 out of 5 average rating, 97 reviews
Cabin in Chestertown
Lake Cabin Retreat
6 beds
22–27 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Chalet in Chestertown
Chalet on Loon Lake (Gore Mt. 20 min.)
5 beds
17–22 Oct
4.98 out of 5 average rating, 175 reviews
Top guest favourite
Home in Chestertown
Adirondack Home 15 minutes to Gore and Lake George
Access to private beach, Kayak
25–30 Jul
5.0 out of 5 average rating, 33 reviews
Superhost
Home in Chestertown
Child-friendly 3BR Adirondacks | Fireplace
4 beds
30 Aug – 4 Sept
4.89 out of 5 average rating, 55 reviews
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
7 beds
23–28 Aug
4.94 out of 5 average rating, 16 reviews
Superhost
Chalet in Warrensburg
Adirondack Chalet on 80 private acres
5 beds
29 Aug – 3 Sept
4.92 out of 5 average rating, 504 reviews
Guest favourite
Home in Chestertown
Chestertown Charm: minutes to Loon Lake
4 beds
26–31 Jul
4.93 out of 5 average rating, 41 reviews
Top guest favourite
Cabin in Warrensburg
Bearpine Cottage
River views
11–16 Aug
4.97 out of 5 average rating, 124 reviews
Guest favourite
Home in Chestertown
Shore fun waterfront lake house Close to Gore Mtn.
4 beds
5–10 Sept
4.83 out of 5 average rating, 12 reviews
Home in Chestertown
Charming Adirondack Home Near Lakes and Trails
5 beds
8–13 Sept
Superhost
Home in Chestertown
The Ramblewood. Family Friendly.
On Loon Lake
19–24 Jul
4.68 out of 5 average rating, 260 reviews
Top guest favourite
Home in Chestertown
The Hayes Homestead
4 beds
23–28 Aug
5.0 out of 5 average rating, 56 reviews
Top guest favourite
Home in Chestertown
The Stone Lodge on Blythewood Island on Loon Lake
6 beds
27 Sept – 2 Oct
4.93 out of 5 average rating, 181 reviews
Guest favourite
Chalet in Warrensburg
Adirondack Riverfront Retreat | Near Lake George
4 beds
13–18 Sept
4.95 out of 5 average rating, 63 reviews