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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
Show price breakdown
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
,
·
1 bathroom
1 bathroom
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)
Superhost
Superhost
Cabin in Plainfield
Camp on Windsor Pond- Berkshires
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$1,659 SGD
$1,445 SGD
Show price breakdown
for 5 nights
4.7 out of 5 average rating, 100 reviews
4.7 (100)
Home in Cummington
Berkshire Hills Nature Lovers' Log Home Retreat
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
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)
Cottage in Plainfield
Windsor Pond spacious get-away cottage
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
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)
Top guest favourite
Guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms
5 bedrooms
,
·
9 beds
9 beds
,
·
3 bathrooms
3 bathrooms
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)
Superhost
Superhost
Cabin in Plainfield
Camp on Windsor Pond Berkshires
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
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)
Top guest favourite
Guest favourite
Home in Plainfield
Berkshire Forest Getaway
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
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)
Top guest favourite
Guest favourite
Home in Hinsdale
Modern Lakehouse with Private Lake Access
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
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)
Guest favourite
Guest favourite
Home in Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms
6 bedrooms
,
·
17 beds
17 beds
,
·
6.5 bathrooms
6.5 bathrooms
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 Savoy
Bear Minimum
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
,
·
2.5 bathrooms
2.5 bathrooms
7–12 Sept
7–12 Sept
$1,755 SGD
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for 5 nights
$1,755 SGD for 5 nights
4.94 out of 5 average rating, 88 reviews
4.94 (88)
Top guest favourite
Guest favourite
Home in Hinsdale
Hummingbird Haven
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
3.5 bathrooms
3.5 bathrooms
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
Guest house in North Adams
Netherwood - North Adams Guest House with Views
3 bedrooms
3 bedrooms
,
·
3 king beds
3 king beds
,
·
3 bathrooms
3 bathrooms
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)
Guest favourite
Guest favourite
Home in Chester
Cozy Retreat for Adventurers, Artists, & Families
2 bedrooms
2 bedrooms
,
·
5 beds
5 beds
,
·
1 bathroom
1 bathroom
5–10 Oct
5–10 Oct
$1,483 SGD
Show price breakdown
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
Berkshire Mountain House
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
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)
Guest favourite
Guest favourite
Home in Cheshire
Large Secluded Berkshire Home
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
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)
Guest favourite
Guest favourite
Home in New Ashford
Rosecroft, Historic Home, Greylock Valley Estate
8 bedrooms
8 bedrooms
,
·
8 beds
8 beds
,
·
3 bathrooms
3 bathrooms
12–17 Sept
12–17 Sept
$3,130 SGD
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for 5 nights
$3,130 SGD for 5 nights
4.92 out of 5 average rating, 233 reviews
4.92 (233)
Guest favourite
Guest favourite
Cabin in Hinsdale
Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
10–15 Sept
10–15 Sept
$2,322 SGD
$1,975 SGD
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for 5 nights
4.93 out of 5 average rating, 139 reviews
4.93 (139)
Home in Worthington
Private Berkshire Chalet in Worthington
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
9–14 Sept
9–14 Sept
$2,250 SGD
$2,025 SGD
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for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
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