Search results; Over 1,000 homes in Chestertown

Guest favorite
Home in Chestertown
Base Camp
3 beds
Aug 1 – 6
R20,481 ZAR for 5 nights
4.89 out of 5 average rating, 9 reviews
Top guest favorite
Home in Chestertown
Adirondack Lake House
Kayak
Aug 23 – 28
R21,114 ZAR for 5 nights
4.95 out of 5 average rating, 239 reviews
Top guest favorite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Fire Pit, Lawn
3 beds
Aug 3 – 8
R23,078 ZAR for 5 nights, originally R33,727 ZAR
4.95 out of 5 average rating, 222 reviews
Guest favorite
Chalet in Chestertown
Chalet on Loon Lake (Gore Mt. 20 min.)
5 beds
Sep 21 – 26
R33,782 ZAR for 5 nights
4.98 out of 5 average rating, 163 reviews
Top guest favorite
Cabin in Chestertown
Posh Camp a Classic Adk Mtn. Cabin & Guide Srvc.
1 queen bed
Aug 1 – 6
R27,765 ZAR for 5 nights
4.99 out of 5 average rating, 77 reviews
Top guest favorite
Room in Warrensburg
Stay with Hanna
ADK Serenity Farmhouse 1.0
Sep 7 – 12
R4,943 ZAR for 5 nights, originally R5,463 ZAR
4.95 out of 5 average rating, 55 reviews
Guest favorite
Room in Warrensburg
Stay with Hanna
ADK Serenity Farmhouse 2.0
Aug 4 – 9
R5,063 ZAR for 5 nights
4.94 out of 5 average rating, 36 reviews
Top guest favorite
Apartment in Chestertown
Rustic Adirondack Studio Apartment
1 queen bed
Sep 10 – 15
R14,252 ZAR for 5 nights
5.0 out of 5 average rating, 112 reviews
Superhost
Home in Chestertown
The Ramblewood. Family Friendly.
On Loon Lake
Aug 18 – 23
R17,391 ZAR for 5 nights, originally R19,505 ZAR
4.66 out of 5 average rating, 243 reviews
Guest favorite
Home in Chestertown
Chestertown Charm close to Gore Mt. Come ski!
4 beds
Aug 13 – 18
R29,349 ZAR for 5 nights
4.9 out of 5 average rating, 31 reviews
Top guest favorite
Barn in Chestertown
Adirondack Base Camp by Loon Lake and Gore Mt.!
7 beds
Sep 7 – 12
R19,742 ZAR for 5 nights
4.98 out of 5 average rating, 84 reviews
Home in Chestertown
Shore Fun Lake House
4 beds
Sep 1 – 6
R32,621 ZAR for 5 nights
Superhost
Cottage in Chestertown
Friends Lake Adirondack Cottage
Kayak
Aug 20 – 25
R21,009 ZAR for 5 nights
4.84 out of 5 average rating, 32 reviews
Top guest favorite
Home in Chestertown
The Hayes Homestead
4 beds
Sep 7 – 12
R24,704 ZAR for 5 nights
5.0 out of 5 average rating, 37 reviews
Guest favorite
Vacation home in Chestertown
Green Mansions Vacation Condo, 2 bedroom & 2 bath
Access to private beachKayak,
Aug 16 – 23
R19,007 ZAR for 7 nights, originally R23,359 ZAR
5.0 out of 5 average rating, 33 reviews
Top guest favorite
Cottage in Chestertown
Private, Loon Lake front cozy cabin on 3 Acres
2 beds
Sep 8 – 13
R22,381 ZAR for 5 nights
4.95 out of 5 average rating, 42 reviews
Guest favorite
Home in Wevertown
A Cozy Creekside Getaway minutes from Gore Mtn.
WaterfrontRiver views,
Aug 1 – 6
R20,924 ZAR for 5 nights
4.97 out of 5 average rating, 146 reviews
Top guest favorite
Home in Chestertown
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
5 beds
Sep 7 – 12
R34,036 ZAR for 5 nights
4.97 out of 5 average rating, 96 reviews