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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

$1,526 SGD for 5 nights

,

4.95 out of 5 average rating, 259 reviews

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

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

Chalet in Chestertown

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

4 bedrooms, 5 beds

17–22 Oct

$2,581 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

18–23 Jul

$2,174 SGD for 5 nights

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Free cancellation

4.92 out of 5 average rating, 39 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

Guest favourite

Home in Chestertown

Adirondack 🏠 near Gore Mt, North Creek, Loon lake.

2 bedrooms, 6 beds

1–6 Aug

$2,402 SGD for 5 nights

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Free cancellation

4.92 out of 5 average rating, 120 reviews

Top guest favourite

Home in Chestertown

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

4 bedrooms, 7 beds

27 Jul – 1 Aug

$2,567 SGD for 5 nights

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Free cancellation

4.97 out of 5 average rating, 68 reviews

Top guest favourite

Home in Chestertown

Waterfront Pond/Walk To Town/Hot Tub/Fire Pit

3 bedrooms, 6 beds

3–8 Aug

$3,140 SGD for 5 nights

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Free cancellation

4.92 out of 5 average rating, 12 reviews

Superhost

Home in Chestertown

The Ramblewood. Family Friendly.

6 bedrooms, 8 beds

19–24 Jul

$1,496 SGD for 5 nights

Free cancellation

4.68 out of 5 average rating, 260 reviews

Cabin in Chestertown

Lake Cabin Retreat

3 bedrooms, 6 beds

22–27 Aug

$2,570 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 3 reviews

Guest favourite

Home in Chestertown

Gorgeous 4BR Lakefront Friends Lake, NY | Dock

4 bedrooms, 6 beds

16–21 Oct

$1,795 SGD for 5 nights

4.88 out of 5 average rating, 60 reviews

Superhost

Home in Chestertown

Child-friendly 3BR Adirondacks | Fireplace

3 bedrooms, 4 beds

29 Aug – 3 Sept

$2,879 SGD for 5 nights

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Free cancellation

4.89 out of 5 average rating, 55 reviews

Home in Chestertown

Charming Adirondack Home Near Lakes and Trails

4 bedrooms, 5 beds

8–13 Sept

$2,839 SGD for 5 nights

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Free cancellation

Guest favourite

Home in Chestertown

Rita's Place

3 bedrooms, 3 beds

9–14 Jul

$2,364 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 23 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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4.98 out of 5 average rating, 65 reviews

Guest favourite

Cabin in Brant Lake

ForeverWild Cabin- Close to LG, Firepit, Pavilion

3 bedrooms, 5 beds

18–23 Jul

$2,662 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 21 reviews

Top guest favourite

Home in Chestertown

Adirondack Home 15 minutes to Gore and Lake George

4 bedrooms, 11 beds

25–30 Jul

Free cancellation

5.0 out of 5 average rating, 33 reviews

Top guest favourite

Cabin in Warrensburg

Bearpine Cottage

2 bedrooms, 5 beds

11–16 Aug

$1,133 SGD for 5 nights

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Free cancellation

4.97 out of 5 average rating, 123 reviews