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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

9–14 Aug

$1,528 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 259 reviews

Top guest favourite

Home in Chestertown

The Hayes Homestead

3 bedrooms, 4 beds

5–10 Jul

$1,902 SGD for 5 nights

5.0 out of 5 average rating, 55 reviews

Top guest favourite

Barn in Chestertown

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

2 bedrooms, 3 beds

12–17 Jul

4.96 out of 5 average rating, 267 reviews

Guest favourite

Home in Chestertown

4 Mi to Beach & Lake: Spacious Home in Chestertown

4 bedrooms, 7 beds

23–28 Aug

$2,077 SGD for 5 nights

4.93 out of 5 average rating, 15 reviews

Home in Chestertown

Charming Adirondack Home Near Lakes and Trails

4 bedrooms, 5 beds

9–14 Aug

Free cancellation

Guest favourite

Home in Chestertown

Chestertown Charm: minutes to Loon Lake

3 bedrooms, 4 beds

5–10 Jul

$2,215 SGD for 5 nights

4.92 out of 5 average rating, 39 reviews

Guest favourite

Home in Chestertown

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

3 bedrooms, 6 beds

5–10 Jul

$2,343 SGD for 5 nights

4.9 out of 5 average rating, 10 reviews

Top guest favourite

Chalet in Chestertown

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

4 bedrooms, 5 beds

17–22 Oct

$2,594 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 174 reviews

Top guest favourite

Home in Chestertown

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

4 bedrooms, 7 beds

9–14 Aug

$2,559 SGD for 5 nights

4.97 out of 5 average rating, 66 reviews

Guest favourite

Cabin in Chestertown

Cozy Adirondack Cabin w/ Fire Pit & Lake Access

4 bedrooms, 8 beds

30 Aug – 4 Sept

$2,904 SGD for 5 nights

4.89 out of 5 average rating, 38 reviews

Top guest favourite

Home in Pottersville

Bring Your Dog | River Dock + Fire Table

2 bedrooms, 2 beds

26–31 Jul

$2,301 SGD for 5 nights

5.0 out of 5 average rating, 10 reviews

Home in Chestertown

Child-friendly 3BR Adirondacks | Fireplace

3 bedrooms, 4 beds

29 Aug – 3 Sept

$2,474 SGD for 5 nights

4.89 out of 5 average rating, 55 reviews

Guest favourite

Home in Chestertown

Rita's Place

3 bedrooms, 3 beds

7–12 Jul

$2,368 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 23 reviews

Guest favourite

Home in Chestertown

Gorgeous 4BR Lakefront Friends Lake, NY | Dock

4 bedrooms, 6 beds

16–21 Oct

$1,798 SGD for 5 nights

4.88 out of 5 average rating, 60 reviews

Guest favourite

Home in Brant Lake

Cottage on Brant Lake

2 bedrooms, 3 beds

12–17 Jul

$1,460 SGD for 5 nights

5.0 out of 5 average rating, 12 reviews

Superhost

Home in Chestertown

The Ramblewood. Family Friendly.

6 bedrooms, 8 beds

19–24 Jul

$1,498 SGD for 5 nights

4.68 out of 5 average rating, 260 reviews

Guest favourite

Home in Chestertown

Adirondack Oasis, 15 Mi to Lake George Village!

3 bedrooms, 6 beds

27 Jul – 1 Aug

4.97 out of 5 average rating, 31 reviews

Guest favourite

Cabin in Brant Lake

ForeverWild Cabin- Close to LG, Firepit, Pavilion

3 bedrooms, 5 beds

18–23 Jul

$2,666 SGD for 5 nights

5.0 out of 5 average rating, 21 reviews