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Search results; Over 1,000 homes in Chestertown

Guest favourite

Home in Chestertown

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

2 bedrooms, 6 beds, 2 private bathrooms

5–10 Jul

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4.92 out of 5 average rating, 120 reviews

Top guest favourite

Home in Chestertown

Adirondack Lake House

2 bedrooms, 3 beds, 1 bathroom

9–14 Aug

$1,524 SGD for 5 nights

4.95 out of 5 average rating, 259 reviews

Top guest favourite

Barn in Chestertown

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

2 bedrooms, 3 beds, 1 bathroom

12–17 Jul

4.96 out of 5 average rating, 267 reviews

Top guest favourite

Home in Chestertown

The Hayes Homestead

3 bedrooms, 4 beds, 2 bathrooms

5–10 Jul

$1,898 SGD for 5 nights

5.0 out of 5 average rating, 55 reviews

Guest favourite

Home in Brant Lake

Cottage on Brant Lake

2 bedrooms, 3 beds, 1 bathroom

12–17 Jul

$1,421 SGD for 5 nights

5.0 out of 5 average rating, 12 reviews

Top guest favourite

Home in Chestertown

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

4 bedrooms, 7 beds, 3 bathrooms

9–14 Aug

$2,553 SGD for 5 nights

4.97 out of 5 average rating, 66 reviews

Guest favourite

Home in Chestertown

Chestertown Charm: minutes to Loon Lake

3 bedrooms, 4 beds, 2.5 bathrooms

5–10 Jul

$2,210 SGD for 5 nights

4.92 out of 5 average rating, 39 reviews

Guest favourite

Home in Chestertown

Rita's Place

3 bedrooms, 3 beds, 2 bathrooms

7–12 Jul

$2,362 SGD for 5 nights

5.0 out of 5 average rating, 23 reviews

Superhost

Chalet in Warrensburg

Adirondack Chalet on 80 private acres

4 bedrooms, 5 beds, 3 bathrooms

9–14 Aug

$3,365 SGD for 5 nights

4.92 out of 5 average rating, 504 reviews

Cabin in Chestertown

Adirondack Overlook at Tripp Lake

3 bedrooms, 7 beds, 3 bathrooms

5–10 Jul

$2,667 SGD for 5 nights

Guest favourite

Home in Chestertown

4 Mi to Beach & Lake: Spacious Home in Chestertown

4 bedrooms, 7 beds, 3 bathrooms

23–28 Aug

$2,073 SGD for 5 nights

4.94 out of 5 average rating, 16 reviews

Cabin in Chestertown

Lake Cabin Retreat

3 bedrooms, 6 beds, 2 bathrooms

5–10 Jul

New place to stay

Superhost

Townhouse in Chestertown

Lakefront Townhome Chestertown "Lakeside Escape"

3 bedrooms, 3 beds, 1.5 bathrooms

7–12 Aug

4.69 out of 5 average rating, 13 reviews

Home in Fort Ann

Lake George Oasis | Heated Pool & Hot Tub

4 bedrooms, 4 beds, 2 bathrooms

9–14 Sept

$3,886 SGD for 5 nights

New place to stay

Guest favourite

Apartment in Chestertown

Evergreen Lakeside Adirondack Retreat

3 bedrooms, 4 beds, 1.5 bathrooms

26–31 Aug

$1,600 SGD for 5 nights

4.89 out of 5 average rating, 36 reviews

Home in Chestertown

Charming Adirondack Home Near Lakes and Trails

4 bedrooms, 5 beds, 2 bathrooms

9–14 Aug

Guest favourite

Cabin in Chestertown

Cozy Adirondack Cabin w/ Fire Pit & Lake Access

4 bedrooms, 8 beds, 2 bathrooms

30 Aug – 4 Sept

$2,916 SGD for 5 nights

4.9 out of 5 average rating, 39 reviews

Guest favourite

Home in Chestertown

Shore fun waterfront lake house Close to Gore Mtn.

3 bedrooms, 4 beds, 2 bathrooms

25–30 Aug

$2,599 SGD for 5 nights

4.82 out of 5 average rating, 11 reviews

Guest favourite

Home in Chestertown

Family friendly Adirondack dream, no cleaning fee!

3 bedrooms, 5 beds, 2 bathrooms

8–13 Sept

$2,909 SGD for 5 nights

4.94 out of 5 average rating, 96 reviews