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Search results; Over 1,000 homes in Windsor
Over 1,000 homes in Windsor
Guest favourite
Guest favourite
Cabin in Windsor
Stone cabin in the Berkshires
2 bedrooms
,
·
3 beds
,
·
1 private bathroom
12–17 Sept
12–17 Sept
$1,878 SGD
$1,660 SGD
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for 5 nights
,
·
4.88 out of 5 average rating, 32 reviews
4.88 (32)
Guest favourite
Guest favourite
Home in Windsor
Beautiful Log Cabin with a Mountain View
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
13–18 Sept
13–18 Sept
$1,867 SGD
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for 5 nights
$1,867 SGD for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Cottage in Plainfield
Windsor Pond spacious get-away cottage
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
7–12 Sept
7–12 Sept
$1,040 SGD
$906 SGD
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for 5 nights
4.8 out of 5 average rating, 41 reviews
4.8 (41)
Home in Cummington
Berkshire Hills Nature Lovers' Log Home Retreat
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
7–12 Sept
7–12 Sept
$3,551 SGD
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for 5 nights
$3,551 SGD for 5 nights
4.89 out of 5 average rating, 18 reviews
4.89 (18)
Superhost
Superhost
Cabin in Plainfield
Camp on Windsor Pond- Berkshires
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
13–18 Sept
13–18 Sept
$1,659 SGD
$1,445 SGD
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for 5 nights
4.7 out of 5 average rating, 100 reviews
4.7 (100)
Top guest favourite
Guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms
5 bedrooms
,
·
9 beds
9 beds
7–12 Sept
7–12 Sept
$2,541 SGD
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for 5 nights
$2,541 SGD for 5 nights
5.0 out of 5 average rating, 20 reviews
5.0 (20)
Top guest favourite
Guest favourite
Home in Plainfield
Berkshire Forest Getaway
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
21–26 Sept
21–26 Sept
$2,028 SGD
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for 5 nights
$2,028 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Guest favourite
Guest favourite
Home in Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms
6 bedrooms
,
·
17 beds
17 beds
13–18 Sept
13–18 Sept
$12,858 SGD
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for 5 nights
$12,858 SGD for 5 nights
5.0 out of 5 average rating, 23 reviews
5.0 (23)
Top guest favourite
Guest favourite
Home in Hinsdale
Modern Lakehouse with Private Lake Access
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
9–14 Sept
9–14 Sept
$3,346 SGD
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for 5 nights
$3,346 SGD for 5 nights
4.97 out of 5 average rating, 31 reviews
4.97 (31)
Top guest favourite
Guest favourite
Guest house in North Adams
Netherwood - North Adams Guest House with Views
3 bedrooms
3 bedrooms
,
·
3 king beds
3 king beds
1–6 Nov
1–6 Nov
$1,755 SGD
$1,540 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 336 reviews
5.0 (336)
Top guest favourite
Guest favourite
Home in Hinsdale
Hummingbird Haven
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
2–7 Oct
2–7 Oct
$2,525 SGD
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for 5 nights
$2,525 SGD for 5 nights
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Top guest favourite
Guest favourite
Home in Lanesborough
Berkshire Mountain House
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
14–19 Sept
14–19 Sept
$3,122 SGD
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for 5 nights
$3,122 SGD for 5 nights
5.0 out of 5 average rating, 42 reviews
5.0 (42)
Superhost
Superhost
Cabin in Plainfield
Camp on Windsor Pond Berkshires
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
13–18 Sept
13–18 Sept
$1,659 SGD
$1,445 SGD
Show price breakdown
for 5 nights
Free cancellation
4.55 out of 5 average rating, 38 reviews
4.55 (38)
Home in Worthington
Private Berkshire Chalet in Worthington
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
9–14 Sept
9–14 Sept
$2,256 SGD
$2,031 SGD
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for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Guest favourite
Guest favourite
Home in Chester
Cozy Retreat for Adventurers, Artists, & Families
2 bedrooms
2 bedrooms
,
·
5 beds
5 beds
5–10 Oct
5–10 Oct
$1,483 SGD
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for 5 nights
$1,483 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 13 reviews
4.92 (13)
Top guest favourite
Guest favourite
Home in Lanesborough
Lakefront Home on Ponstoosuc Lake, The Berkshires
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
8–13 Sept
8–13 Sept
$3,667 SGD
$3,375 SGD
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for 5 nights
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Top guest favourite
Guest favourite
Chalet in Peru
Swiss Chalet Style Timberframe Home in Berkshires
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
20–25 Sept
20–25 Sept
$2,147 SGD
$1,887 SGD
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for 5 nights
Free cancellation
4.93 out of 5 average rating, 311 reviews
4.93 (311)
Guest favourite
Guest favourite
Home in Cheshire
Large Secluded Berkshire Home
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
7–12 Sept
7–12 Sept
$2,945 SGD
$2,612 SGD
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for 5 nights
4.81 out of 5 average rating, 165 reviews
4.81 (165)
Top guest favourite
Guest favourite
Guest house in Cummington
Cozy Hilltown Cottage
1 bedroom
1 bedroom
,
·
2 beds
2 beds
5–10 Oct
5–10 Oct
$1,413 SGD
Show price breakdown
for 5 nights
$1,413 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 221 reviews
4.99 (221)
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