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Search results; Over 1,000 homes in Chestertown

Top guest favourite

Barn in Chestertown

Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+

2 bedrooms, 3 beds, 1 private bathroom

1–6 Aug

,

4.96 out of 5 average rating, 273 reviews

Top guest favourite

Home in Chestertown

Adirondack Lake House

2 bedrooms, 3 beds, 1 bathroom

26–31 Aug

$1,520 SGD for 5 nights

4.95 out of 5 average rating, 265 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, 28 reviews

Cottage in Chestertown

Private Dock & Beach! Lakefront, Fire Pit, Boats

2 bedrooms, 2 beds, 1 bathroom

30 Aug – 4 Sept

$3,122 SGD for 5 nights

Cabin in Chestertown

Lake Cabin Retreat

3 bedrooms, 6 beds, 2 bathrooms

9–14 Sept

$2,613 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Superhost

Home in Chestertown

Child-friendly 3BR Adirondacks | Fireplace

3 bedrooms, 4 beds, 2 bathrooms

14–19 Sept

$2,394 SGD for 5 nights

4.89 out of 5 average rating, 56 reviews

Guest favourite

Home in Chestertown

Gorgeous 4BR Lakefront Friends Lake, NY | Dock

4 bedrooms, 6 beds, 3.5 bathrooms

9–14 Oct

$1,838 SGD for 5 nights

4.88 out of 5 average rating, 60 reviews

Guest favourite

Home in Chestertown

4 Mi to Beach & Lake: Spacious Home in Chestertown

4 bedrooms, 7 beds, 3 bathrooms

30 Aug – 4 Sept

$2,066 SGD for 5 nights

4.94 out of 5 average rating, 16 reviews

Top guest favourite

Home in Chestertown

The Hayes Homestead

3 bedrooms, 4 beds, 2 bathrooms

23–28 Aug

$1,837 SGD for 5 nights

5.0 out of 5 average rating, 58 reviews

Guest favourite

Home in Chestertown

Family friendly Adirondack dream, no cleaning fee!

3 bedrooms, 5 beds, 2 bathrooms

8–13 Sept

$2,900 SGD for 5 nights

4.94 out of 5 average rating, 97 reviews

Top guest favourite

Home in Chestertown

Pond Farmhouse: Private Hot Tub, Fire Pit, Town

3 bedrooms, 6 beds, 1 bathroom

3–8 Aug

$2,164 SGD for 5 nights

4.92 out of 5 average rating, 13 reviews

Top guest favourite

Home in Chestertown

The Stone Lodge on Blythewood Island on Loon Lake

4 bedrooms, 6 beds, 2.5 bathrooms

27 Sept – 2 Oct

$3,229 SGD for 5 nights

4.93 out of 5 average rating, 181 reviews

Top guest favourite

Home in Adirondack

Adirondack Owl's Nest Guest House

4 bedrooms, 4 beds, 2 bathrooms

31 Aug – 5 Sept

$1,922 SGD for 5 nights

5.0 out of 5 average rating, 184 reviews

Guest favourite

Home in Chestertown

House in the Adirondacks, 15 min from Gore!

3 bedrooms, 5 beds, 2.5 bathrooms

28 Aug – 2 Sept

$2,140 SGD for 5 nights

4.93 out of 5 average rating, 42 reviews

Top guest favourite

Home in Chestertown

Blue Bay Retreat - Loon Lake Lakefront w/ Hot Tub

4 bedrooms, 9 beds, 2 bathrooms

29 Aug – 3 Sept

$4,854 SGD for 5 nights

5.0 out of 5 average rating, 72 reviews

Home in Chestertown

Charming Adirondack Home Near Lakes and Trails

4 bedrooms, 5 beds, 2 bathrooms

8–13 Sept

$2,820 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Guest favourite

Cabin in Chestertown

Adirondack Overlook at Tripp Lake

3 bedrooms, 7 beds, 3 bathrooms

22–27 Aug

$2,539 SGD for 5 nights

4.83 out of 5 average rating, 6 reviews

Superhost

Cottage in Chestertown

Friends Lake Adirondack Cottage

3 bedrooms, 4 beds, 1 bathroom

18–23 Aug

$1,665 SGD for 5 nights

4.85 out of 5 average rating, 40 reviews

Top guest favourite

Home in Chestertown

Modern ADK House-Lake and Mountain View-Sleeps 16

4 bedrooms, 11 beds, 2.5 bathrooms

22–27 Aug

5.0 out of 5 average rating, 35 reviews