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Search results; Over 1,000 homes in Chestertown

Guest favourite

Cabin in Chestertown

Meadow House

5 bedrooms, 9 beds, 3 private bathrooms

23–28 Aug

$2,286 SGD for 5 nights

,

4.88 out of 5 average rating, 165 reviews

Top guest favourite

Home in Chestertown

Adirondack Lake House

2 bedrooms, 3 beds

6–11 Sept

$1,509 SGD for 5 nights

Pay $0 today

Free cancellation

4.95 out of 5 average rating, 266 reviews

Top guest favourite

Barn in Chestertown

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

2 bedrooms, 3 beds

25–30 Aug

$2,002 SGD for 5 nights

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Free cancellation

4.96 out of 5 average rating, 275 reviews

Cottage in Chestertown

Private Dock & Beach! Lakefront, Fire Pit, Boats

2 bedrooms, 2 beds

23–28 Aug

$2,676 SGD for 5 nights

Cabin in Chestertown

Lake Cabin Retreat

3 bedrooms, 6 beds

9–14 Sept

$2,528 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 4 reviews

Home in Chestertown

Enchanted Chestertown Getaway

3 bedrooms, 4 beds

8–13 Sept

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Free cancellation

New place to stay

Top guest favourite

Cabin in Chestertown

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

1 bedroom, 1 queen bed

14–19 Aug

$2,074 SGD for 5 nights

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Free cancellation

4.98 out of 5 average rating, 90 reviews

Top guest favourite

Home in Chestertown

The Hayes Homestead

3 bedrooms, 4 beds

23–28 Aug

$1,824 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 58 reviews

Guest favourite

Cabin in Town of Johnsburg

2 bdrm ADK cabin 10 mins to GORE MTN

2 bedrooms, 3 beds

22–27 Sept

$1,595 SGD for 5 nights

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Free cancellation

4.97 out of 5 average rating, 162 reviews

Top guest favourite

Flat in Chestertown

Rustic Adirondack Studio Apartment

1 bedroom, 1 queen bed

4–9 Oct

$992 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 121 reviews

Top guest favourite

Home in Chestertown

Pond Farmhouse: Private Hot Tub, Fire Pit, Town

3 bedrooms, 6 beds

19–24 Sept

$2,186 SGD for 5 nights

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Free cancellation

4.92 out of 5 average rating, 13 reviews

Top guest favourite

Cabin in Warrensburg

Bearpine Cottage

2 bedrooms, 5 beds

9–14 Nov

$1,120 SGD for 5 nights

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Free cancellation

4.97 out of 5 average rating, 129 reviews

Superhost

Cabin in Chestertown

Quaint Adirondack Condo

1 bedroom, 3 beds

13–18 Sept

$1,220 SGD for 5 nights

4.79 out of 5 average rating, 29 reviews

Top guest favourite

Cabin in Chestertown

Adirondack Overlook at Tripp Lake

3 bedrooms, 7 beds

22–27 Aug

$2,535 SGD for 5 nights

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Free cancellation

4.86 out of 5 average rating, 7 reviews

Top guest favourite

Cabin in Chestertown

Pine Tree Cove on Friends Lake

4 bedrooms, 12 beds

30 Aug – 4 Sept

$8,007 SGD for 5 nights

4.98 out of 5 average rating, 81 reviews

Guest favourite

Apartment in Chestertown

Evergreen Lakeside Adirondack Retreat

3 bedrooms, 4 beds

26–31 Aug

$1,584 SGD for 5 nights

4.89 out of 5 average rating, 36 reviews

Guest favourite

Home in Chestertown

House in the Adirondacks, 15 min from Gore!

3 bedrooms, 5 beds

28 Aug – 2 Sept

$2,186 SGD for 5 nights

4.93 out of 5 average rating, 42 reviews

Home in Chestertown

Charming Adirondack Home Near Lakes and Trails

4 bedrooms, 5 beds

8–13 Sept

$2,791 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 4 reviews

Guest favourite

Barn in Chestertown

Adirondack Base Camp by Loon Lake and Gore Mt.!

2 bedrooms, 7 beds

6–11 Sept

$1,352 SGD for 5 nights

4.95 out of 5 average rating, 103 reviews