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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

5–10 Jul

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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

$1,528 SGD for 5 nights

4.95 out of 5 average rating, 259 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, 267 reviews

Top guest favourite

Home in Chestertown

The Hayes Homestead

3 bedrooms, 4 beds, 2 bathrooms

5–10 Jul

$1,902 SGD for 5 nights

5.0 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

9–14 Aug

$2,559 SGD for 5 nights

4.97 out of 5 average rating, 66 reviews

Guest favourite

Home in Chestertown

Chestertown Charm: minutes to Loon Lake

3 bedrooms, 4 beds, 2.5 bathrooms

5–10 Jul

$2,215 SGD for 5 nights

4.92 out of 5 average rating, 39 reviews

Cabin in Chestertown

Adirondack Overlook at Tripp Lake

3 bedrooms, 7 beds, 3 bathrooms

5–10 Jul

$2,673 SGD for 5 nights

Guest favourite

Home in Chestertown

4 Mi to Beach & Lake: Spacious Home in Chestertown

4 bedrooms, 7 beds, 3 bathrooms

23–28 Aug

$2,077 SGD for 5 nights

4.93 out of 5 average rating, 15 reviews

Superhost

Chalet in Warrensburg

Adirondack Chalet on 80 private acres

4 bedrooms, 5 beds, 3 bathrooms

9–14 Aug

$3,373 SGD for 5 nights

4.92 out of 5 average rating, 504 reviews

Cabin in Chestertown

Lake Cabin Retreat

3 bedrooms, 6 beds, 2 bathrooms

22–27 Aug

$2,574 SGD for 5 nights

New place to stay

Guest favourite

Cabin in Chestertown

Cozy Adirondack Cabin w/ Fire Pit & Lake Access

4 bedrooms, 8 beds, 2 bathrooms

30 Aug – 4 Sept

$2,922 SGD for 5 nights

4.9 out of 5 average rating, 39 reviews

Guest favourite

Home in Brant Lake

Cottage on Brant Lake

2 bedrooms, 3 beds, 1 bathroom

12–17 Jul

$1,425 SGD for 5 nights

5.0 out of 5 average rating, 12 reviews

Top guest favourite

Chalet in Chestertown

The Roost, a lake front 4 season home

4 bedrooms, 7 beds, 3 bathrooms

13–18 Sept

$3,628 SGD for 5 nights

4.98 out of 5 average rating, 65 reviews

Guest favourite

Townhouse in Chestertown

Secluded and Cozy Townhome at Tripp Lake

3 bedrooms, 3 beds, 2.5 bathrooms

22–27 Aug

Extended stay discount

4.96 out of 5 average rating, 27 reviews

Guest favourite

Home in Chestertown

Family friendly Adirondack dream, no cleaning fee!

3 bedrooms, 5 beds, 2 bathrooms

8–13 Sept

$2,916 SGD for 5 nights

4.94 out of 5 average rating, 96 reviews

Home in Chestertown

Charming Adirondack Home Near Lakes and Trails

4 bedrooms, 5 beds, 2 bathrooms

9–14 Aug

Home in Fort Ann

Lake George Oasis | Heated Pool & Hot Tub

4 bedrooms, 4 beds, 2 bathrooms

9–14 Sept

$3,895 SGD for 5 nights

New place to stay

Guest favourite

Home in Chestertown

Shore fun waterfront lake house Close to Gore Mtn.

3 bedrooms, 4 beds, 2 bathrooms

25–30 Aug

$2,605 SGD for 5 nights

4.82 out of 5 average rating, 11 reviews

Top guest favourite

Cabin in Warrensburg

Bearpine Cottage

2 bedrooms, 5 beds, 1 bathroom

26–31 Oct

$1,134 SGD for 5 nights

4.97 out of 5 average rating, 123 reviews