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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, 260 reviews

Top guest favourite

Barn in Chestertown

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

2 bedrooms, 3 beds

12–17 Jul

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Free cancellation

4.96 out of 5 average rating, 269 reviews

Top guest favourite

Home in Chestertown

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

4 bedrooms, 7 beds

27 Jul – 1 Aug

$2,554 SGD for 5 nights

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Free cancellation

4.97 out of 5 average rating, 68 reviews

Cabin in Chestertown

Lake Cabin Retreat

3 bedrooms, 6 beds

22–27 Aug

$2,569 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 3 reviews

Guest favourite

Home in Chestertown

Family friendly Adirondack dream, no cleaning fee!

3 bedrooms, 5 beds

8–13 Sept

$2,911 SGD for 5 nights

4.94 out of 5 average rating, 97 reviews

Top guest favourite

Cabin in Warrensburg

Bearpine Cottage

2 bedrooms, 5 beds

11–16 Aug

$1,132 SGD for 5 nights

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Free cancellation

4.97 out of 5 average rating, 123 reviews

Top guest favourite

Home in Chestertown

Adirondack Home 15 minutes to Gore and Lake George

4 bedrooms, 11 beds

25–30 Jul

5.0 out of 5 average rating, 33 reviews

Home in Chestertown

Charming Adirondack Home Near Lakes and Trails

4 bedrooms, 5 beds

8–13 Sept

$2,821 SGD for 5 nights

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Free cancellation

Top guest favourite

Home in Chestertown

The Hayes Homestead

3 bedrooms, 4 beds

23–28 Aug

$1,899 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 56 reviews

Guest favourite

Apartment in Chestertown

Evergreen Lakeside Adirondack Retreat

3 bedrooms, 4 beds

26–31 Aug

$1,601 SGD for 5 nights

4.89 out of 5 average rating, 36 reviews

Guest favourite

Home in Chestertown

4 Mi to Beach & Lake: Spacious Home in Chestertown

4 bedrooms, 7 beds

23–28 Aug

$2,074 SGD for 5 nights

4.94 out of 5 average rating, 16 reviews

Top guest favourite

Home in Chestertown

Big Bear Lodge w/ Hot Tub and Sauna

2 bedrooms, 6 beds

27 Aug – 1 Sept

$2,478 SGD for 5 nights

4.93 out of 5 average rating, 70 reviews

Top guest favourite

Home in Chestertown

The Stone Lodge on Blythewood Island on Loon Lake

4 bedrooms, 6 beds

27 Sept – 2 Oct

$2,859 SGD for 5 nights

4.93 out of 5 average rating, 181 reviews

Home in Chestertown

3BR house, lake access, sandy beach, fireplace

3 bedrooms, 4 beds

3–8 Aug

$2,189 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Chalet in Chestertown

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

4 bedrooms, 5 beds

17–22 Oct

$2,591 SGD for 5 nights

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Free cancellation

4.98 out of 5 average rating, 175 reviews

Guest favourite

Home in Chestertown

Chestertown Charm: minutes to Loon Lake

3 bedrooms, 4 beds

26–31 Jul

$2,211 SGD for 5 nights

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Free cancellation

4.92 out of 5 average rating, 39 reviews

Guest favourite

Cabin in Brant Lake

ForeverWild Cabin- Close to LG, Firepit, Pavilion

3 bedrooms, 5 beds

18–23 Jul

$2,661 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 21 reviews

Top guest favourite

Chalet in Chestertown

The Roost, a lake front 4 season home

4 bedrooms, 7 beds

13–18 Sept

$3,622 SGD for 5 nights

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Free cancellation

4.98 out of 5 average rating, 65 reviews

Top guest favourite

Cabin in Chestertown

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

1 bedroom, 1 queen bed

13–18 Jul

$2,097 SGD for 5 nights

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Free cancellation

4.99 out of 5 average rating, 86 reviews