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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

25–30 Aug

$2,573 SGD for 5 nights

,

4.96 out of 5 average rating, 275 reviews

Top guest favourite

Home in Chestertown

Adirondack Lake House

2 bedrooms, 3 beds, 1 bathroom

6–11 Sept

$1,509 SGD for 5 nights

4.96 out of 5 average rating, 267 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

$3,207 SGD for 5 nights

4.93 out of 5 average rating, 182 reviews

Cabin in Chestertown

Lake Cabin Retreat

3 bedrooms, 6 beds, 2 bathrooms

9–14 Sept

$2,528 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Home in Chestertown

The Hayes Homestead

3 bedrooms, 4 beds, 2 bathrooms

26–31 Aug

$1,824 SGD for 5 nights

5.0 out of 5 average rating, 58 reviews

Top guest favourite

Home in Chestertown

Modern ADK House-Lake and Mountain View-Sleeps 16

4 bedrooms, 11 beds, 2.5 bathrooms

4–9 Oct

$5,130 SGD for 5 nights

5.0 out of 5 average rating, 37 reviews

Superhost

Home in Chestertown

Child-friendly 3BR Adirondacks | Fireplace

3 bedrooms, 4 beds, 2 bathrooms

14–19 Sept

$2,377 SGD for 5 nights

4.89 out of 5 average rating, 57 reviews

Cottage in Chestertown

Private Dock & Beach! Lakefront, Fire Pit, Boats

2 bedrooms, 2 beds, 1 bathroom

23–28 Aug

$2,569 SGD for 5 nights

Guest favourite

Home in Chestertown

Gorgeous 4BR Lakefront Friends Lake, NY | Dock

4 bedrooms, 6 beds, 3.5 bathrooms

13–18 Oct

$1,726 SGD for 5 nights

4.88 out of 5 average rating, 60 reviews

Home in Chestertown

Charming Adirondack Home Near Lakes and Trails

4 bedrooms, 5 beds, 2 bathrooms

31 Aug – 5 Sept

$2,792 SGD for 5 nights

5.0 out of 5 average rating, 4 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

$2,052 SGD for 5 nights

4.94 out of 5 average rating, 17 reviews

Guest favourite

Townhouse in Chestertown

Secluded and Cozy Townhome at Tripp Lake

3 bedrooms, 3 beds, 2.5 bathrooms

29 Aug – 3 Sept

Extended stay discount

4.96 out of 5 average rating, 28 reviews

Home in Chestertown

Enchanted Chestertown Getaway

3 bedrooms, 4 beds, 1.5 bathrooms

8–13 Sept

New place to stay

Guest favourite

Cabin in Chestertown

Posh Camp a Classic Adk Mtn. Cabin & Guide Srvc.

1 bedroom, 1 queen bed, 1 bathroom

14–19 Aug

$2,075 SGD for 5 nights

4.98 out of 5 average rating, 90 reviews

Top guest favourite

Cabin in Chestertown

Adirondack Overlook at Tripp Lake

3 bedrooms, 7 beds, 3 bathrooms

27 Aug – 1 Sept

$2,559 SGD for 5 nights

4.86 out of 5 average rating, 7 reviews

Guest favourite

Home in Chestertown

Family friendly Adirondack dream, no cleaning fee!

3 bedrooms, 5 beds, 2 bathrooms

8–13 Sept

$2,880 SGD for 5 nights

4.94 out of 5 average rating, 97 reviews

Guest favourite

Cottage in Chestertown

Private Loon Lake property, cozy cabin on 3 Acres

2 bedrooms, 2 beds, 1 bathroom

7–12 Sept

$1,636 SGD for 5 nights

4.93 out of 5 average rating, 55 reviews

Guest favourite

Chalet in Chestertown

Loon Lake Luxury with Kayaks, Canoe, Hot Tub

3 bedrooms, 6 beds, 3 bathrooms

29 Aug – 5 Sept

4.91 out of 5 average rating, 56 reviews

Top guest favourite

Holiday home in Chestertown

Green Mansions Vacation Condo, 2 bedroom & 2 bath

2 bedrooms, 2 bathrooms

22–29 Aug

Weekly discount

4.96 out of 5 average rating, 45 reviews