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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

$1,525 SGD for 5 nights

,

4.95 out of 5 average rating, 261 reviews

Guest favourite

Cottage in Chestertown

Private Loon Lake property, cozy cabin on 3 Acres

2 bedrooms, 2 beds, 1 bathroom

7–12 Sept

$1,700 SGD for 5 nights

4.92 out of 5 average rating, 53 reviews

Top guest favourite

Flat in Chestertown

Rustic Adirondack Studio Apartment

1 bedroom, 1 queen bed, 1 bathroom

30 Aug – 4 Sept

$1,003 SGD for 5 nights

5.0 out of 5 average rating, 120 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, 270 reviews

Guest favourite

Barn in Chestertown

Adirondack Base Camp by Loon Lake and Gore Mt.!

2 bedrooms, 7 beds, 1 bathroom

17–22 Aug

$1,601 SGD for 5 nights

4.95 out of 5 average rating, 103 reviews

Guest favourite

Home in Chestertown

Gorgeous 4BR Lakefront Friends Lake, NY | Dock

4 bedrooms, 6 beds, 3.5 bathrooms

16–21 Oct

$1,796 SGD for 5 nights

4.88 out of 5 average rating, 60 reviews

Top guest favourite

Home in Chestertown

Cozy Adk Victorian! Ski, hike, hottub, relax!

4 bedrooms, 7 beds, 3 bathrooms

27 Jul – 1 Aug

$2,553 SGD for 5 nights

4.97 out of 5 average rating, 68 reviews

Top guest favourite

Home in Warrensburg

River House

3 bedrooms, 8 beds, 2.5 bathrooms

31 Aug – 5 Sept

$2,118 SGD for 5 nights

4.97 out of 5 average rating, 63 reviews

Top guest favourite

Cabin in Warrensburg

Bearpine Cottage

2 bedrooms, 5 beds, 1 bathroom

11–16 Aug

$1,132 SGD for 5 nights

4.97 out of 5 average rating, 123 reviews

Guest favourite

Home in Chestertown

Family friendly Adirondack dream, no cleaning fee!

3 bedrooms, 5 beds, 2 bathrooms

8–13 Sept

$2,910 SGD for 5 nights

4.94 out of 5 average rating, 97 reviews

Guest favourite

Cabin in Brant Lake

ForeverWild Cabin- Close to LG, Firepit, Pavilion

3 bedrooms, 5 beds, 2 bathrooms

18–23 Jul

$2,660 SGD for 5 nights

5.0 out of 5 average rating, 21 reviews

Guest favourite

Home in Chestertown

4 Mi to Beach & Lake: Spacious Home in Chestertown

4 bedrooms, 7 beds, 3 bathrooms

23–28 Aug

$2,073 SGD for 5 nights

4.94 out of 5 average rating, 16 reviews

Top guest favourite

Home in Adirondack

Adirondack Owl's Nest Guest House

4 bedrooms, 4 beds, 2 bathrooms

24–29 Aug

$1,928 SGD for 5 nights

5.0 out of 5 average rating, 181 reviews

Cabin in Chestertown

Lake Cabin Retreat

3 bedrooms, 6 beds, 2 bathrooms

22–27 Aug

$2,568 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in Pottersville

Bring Your Dog | River Dock + Fire Table

2 bedrooms, 2 beds, 1 bathroom

26–31 Jul

$2,296 SGD for 5 nights

5.0 out of 5 average rating, 10 reviews

Top guest favourite

Chalet in Chestertown

Chalet on Loon Lake (Gore Mt. 20 min.)

4 bedrooms, 5 beds, 2 bathrooms

17–22 Oct

$2,581 SGD for 5 nights

4.98 out of 5 average rating, 175 reviews

Guest favourite

Home in Chestertown

House in the Adirondacks, 15 min from Gore!

3 bedrooms, 5 beds, 2.5 bathrooms

22–27 Aug

$2,741 SGD for 5 nights

4.93 out of 5 average rating, 42 reviews

Guest favourite

Home in Chestertown

Shore fun waterfront lake house Close to Gore Mtn.

3 bedrooms, 4 beds, 2 bathrooms

25–30 Aug

$2,533 SGD for 5 nights

4.83 out of 5 average rating, 12 reviews

Guest favourite

Home in Pottersville

The Schoolhouse

2 bedrooms, 3 beds, 2 bathrooms

12–17 Jul

$1,445 SGD for 5 nights

4.93 out of 5 average rating, 15 reviews