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Search results; Over 1,000 homes in Chestertown

Chalet in Chestertown

Lake George Adirondack stye house

5 bedrooms, 8 beds, 2 private bathrooms

23–28 Aug

$4,113 SGD for 5 nights

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4.8 out of 5 average rating, 198 reviews

Top guest favourite

Home in Chestertown

Adirondack Lake House

2 bedrooms, 3 beds, 1 bathroom

26–31 Aug

$1,524 SGD for 5 nights

4.95 out of 5 average rating, 262 reviews

Top guest favourite

Barn in Chestertown

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

2 bedrooms, 3 beds, 1 bathroom

20–25 Jul

4.96 out of 5 average rating, 272 reviews

Top guest favourite

Home in Chestertown

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

4 bedrooms, 7 beds, 3 bathrooms

27 Jul – 1 Aug

$2,500 SGD for 5 nights

4.97 out of 5 average rating, 68 reviews

Guest favourite

Home in Chestertown

4 Mi to Beach & Lake: Spacious Home in Chestertown

4 bedrooms, 7 beds, 3 bathrooms

23–28 Aug

$2,072 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

9–14 Sept

$2,620 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Guest favourite

Home in Chestertown

Family friendly Adirondack dream, no cleaning fee!

3 bedrooms, 5 beds, 2 bathrooms

8–13 Sept

$2,908 SGD for 5 nights

4.94 out of 5 average rating, 97 reviews

Top guest favourite

Home in Chestertown

Modern ADK House-Lake and Mountain View-Sleeps 16

4 bedrooms, 11 beds, 2.5 bathrooms

25–30 Jul

$6,390 SGD for 5 nights

5.0 out of 5 average rating, 35 reviews

Home in Chestertown

Charming Adirondack Home Near Lakes and Trails

4 bedrooms, 5 beds, 2 bathrooms

8–13 Sept

$2,818 SGD for 5 nights

Guest favourite

Cabin in Brant Lake

ForeverWild Cabin- Close to LG, Firepit, Pavilion

3 bedrooms, 5 beds, 2 bathrooms

21–26 Jul

$2,735 SGD for 5 nights

5.0 out of 5 average rating, 22 reviews

Top guest favourite

Chalet in Chestertown

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

4 bedrooms, 5 beds, 2 bathrooms

17–22 Oct

$2,576 SGD for 5 nights

4.98 out of 5 average rating, 175 reviews

Top guest favourite

Home in Chestertown

The Stone Lodge on Blythewood Island on Loon Lake

4 bedrooms, 6 beds, 2.5 bathrooms

27 Sept – 2 Oct

$3,237 SGD for 5 nights

4.93 out of 5 average rating, 181 reviews

Superhost

Chalet in Warrensburg

Adirondack Chalet on 80 private acres

4 bedrooms, 5 beds, 3 bathrooms

29 Aug – 3 Sept

$3,239 SGD for 5 nights

4.92 out of 5 average rating, 507 reviews

Top guest favourite

Home in Adirondack

Adirondack Owl's Nest Guest House

4 bedrooms, 4 beds, 2 bathrooms

24–29 Aug

$1,927 SGD for 5 nights

5.0 out of 5 average rating, 183 reviews

Guest favourite

Home in Chestertown

Chestertown Charm: minutes to Loon Lake

3 bedrooms, 4 beds, 2.5 bathrooms

26–31 Jul

$2,209 SGD for 5 nights

4.93 out of 5 average rating, 41 reviews

Guest favourite

Home in Chestertown

Shore fun waterfront lake house Close to Gore Mtn.

3 bedrooms, 4 beds, 2 bathrooms

5–10 Sept

$2,559 SGD for 5 nights

4.85 out of 5 average rating, 13 reviews

Home in Fort Ann

Lake George Oasis | Heated Pool & Hot Tub

4 bedrooms, 4 beds, 2 bathrooms

28 Sept – 3 Oct

$3,898 SGD for 5 nights

New place to stay

Guest favourite

Home in Chestertown

House in the Adirondacks, 15 min from Gore!

3 bedrooms, 5 beds, 2.5 bathrooms

28 Aug – 2 Sept

4.93 out of 5 average rating, 42 reviews

Guest favourite

Barn in Chestertown

Adirondack Base Camp by Loon Lake and Gore Mt.!

2 bedrooms, 7 beds, 1 bathroom

6–11 Sept

$1,454 SGD for 5 nights

4.95 out of 5 average rating, 103 reviews