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Search results; Over 1,000 homes in Chestertown
Over 1,000 homes in Chestertown
Top guest favourite
Guest favourite
Barn in Chestertown
Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+
2 bedrooms
,
·
3 beds
,
·
1 private bathroom
1–6 Aug
1–6 Aug
$2,035 SGD
$1,659 SGD
Show price breakdown
for 5 nights
,
·
4.96 out of 5 average rating, 273 reviews
4.96 (273)
Top guest favourite
Guest favourite
Home in Chestertown
Adirondack Lake House
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
26–31 Aug
26–31 Aug
$1,520 SGD
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for 5 nights
$1,520 SGD for 5 nights
4.95 out of 5 average rating, 265 reviews
4.95 (265)
Cabin in Chestertown
Lake Cabin Retreat
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
9–14 Sept
9–14 Sept
$2,613 SGD
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for 5 nights
$2,613 SGD for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Cabin in Chestertown
The Curley Cabin
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
1–6 Sept
1–6 Sept
$1,676 SGD
Show price breakdown
for 5 nights
$1,676 SGD for 5 nights
New place to stay
New
Guest favourite
Guest favourite
Townhouse in Chestertown
Secluded and Cozy Townhome at Tripp Lake
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
22–27 Aug
22–27 Aug
$1,967 SGD
$1,799 SGD
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for 5 nights
Extended stay discount
4.96 out of 5 average rating, 28 reviews
4.96 (28)
Cottage in Chestertown
Private Dock & Beach! Lakefront, Fire Pit, Boats
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
30 Aug – 4 Sept
30 Aug – 4 Sept
$3,122 SGD
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for 5 nights
$3,122 SGD for 5 nights
Guest favourite
Guest favourite
Home in Chestertown
Gorgeous 4BR Lakefront Friends Lake, NY | Dock
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
3.5 bathrooms
3.5 bathrooms
9–14 Oct
9–14 Oct
$1,838 SGD
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for 5 nights
$1,838 SGD for 5 nights
4.88 out of 5 average rating, 60 reviews
4.88 (60)
Superhost
Superhost
Home in Chestertown
Child-friendly 3BR Adirondacks | Fireplace
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
14–19 Sept
14–19 Sept
$2,394 SGD
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for 5 nights
$2,394 SGD for 5 nights
4.89 out of 5 average rating, 56 reviews
4.89 (56)
Guest favourite
Guest favourite
Home in Chestertown
4 Mi to Beach & Lake: Spacious Home in Chestertown
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
30 Aug – 4 Sept
30 Aug – 4 Sept
$2,066 SGD
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for 5 nights
$2,066 SGD for 5 nights
4.94 out of 5 average rating, 16 reviews
4.94 (16)
Guest favourite
Guest favourite
Home in Chestertown
Family friendly Adirondack dream, no cleaning fee!
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
8–13 Sept
8–13 Sept
$2,900 SGD
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for 5 nights
$2,900 SGD for 5 nights
4.94 out of 5 average rating, 97 reviews
4.94 (97)
Superhost
Superhost
Home in Chestertown
Forest Lake Haven Main House
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
10–15 Aug
10–15 Aug
$3,094 SGD
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for 5 nights
$3,094 SGD for 5 nights
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Top guest favourite
Guest favourite
Home in Chestertown
The Hayes Homestead
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
23–28 Aug
23–28 Aug
$1,837 SGD
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for 5 nights
$1,837 SGD for 5 nights
5.0 out of 5 average rating, 58 reviews
5.0 (58)
Top guest favourite
Guest favourite
Home in Chestertown
The Stone Lodge on Blythewood Island on Loon Lake
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
2.5 bathrooms
2.5 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$3,229 SGD
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for 5 nights
$3,229 SGD for 5 nights
4.93 out of 5 average rating, 181 reviews
4.93 (181)
Top guest favourite
Guest favourite
Home in Chestertown
Pond Farmhouse: Private Hot Tub, Fire Pit, Town
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
1 bathroom
1 bathroom
3–8 Aug
3–8 Aug
$2,019 SGD
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for 5 nights
$2,019 SGD for 5 nights
4.92 out of 5 average rating, 13 reviews
4.92 (13)
Top guest favourite
Guest favourite
Home in Chestertown
Blue Bay Retreat - Loon Lake Lakefront w/ Hot Tub
4 bedrooms
4 bedrooms
,
·
9 beds
9 beds
,
·
2 bathrooms
2 bathrooms
29 Aug – 3 Sept
29 Aug – 3 Sept
$4,854 SGD
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for 5 nights
$4,854 SGD for 5 nights
5.0 out of 5 average rating, 72 reviews
5.0 (72)
Guest favourite
Guest favourite
Home in Chestertown
House in the Adirondacks, 15 min from Gore!
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
28 Aug – 2 Sept
28 Aug – 2 Sept
$2,140 SGD
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for 5 nights
$2,140 SGD for 5 nights
4.93 out of 5 average rating, 42 reviews
4.93 (42)
Top guest favourite
Guest favourite
Home in Chestertown
Modern ADK House-Lake and Mountain View-Sleeps 16
4 bedrooms
4 bedrooms
,
·
11 beds
11 beds
,
·
2.5 bathrooms
2.5 bathrooms
22–27 Aug
22–27 Aug
$6,472 SGD
$4,854 SGD
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for 5 nights
5.0 out of 5 average rating, 35 reviews
5.0 (35)
Guest favourite
Guest favourite
Cabin in Chestertown
Adirondack Overlook at Tripp Lake
3 bedrooms
3 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
22–27 Aug
22–27 Aug
$2,539 SGD
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for 5 nights
$2,539 SGD for 5 nights
4.83 out of 5 average rating, 6 reviews
4.83 (6)
Top guest favourite
Guest favourite
Home in Adirondack
Adirondack Owl's Nest Guest House
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
31 Aug – 5 Sept
31 Aug – 5 Sept
$1,922 SGD
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for 5 nights
$1,922 SGD for 5 nights
5.0 out of 5 average rating, 184 reviews
5.0 (184)
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