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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)
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
$1,658 SGD
$1,445 SGD
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for 5 nights
Free cancellation
4.7 out of 5 average rating, 99 reviews
4.7 (99)
Top guest favourite
Guest favourite
Cottage in Hinsdale
Cozy Cottage in the Berkshires
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
23–28 Oct
23–28 Oct
$1,755 SGD
Show price breakdown
for 5 nights
$1,755 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 168 reviews
4.99 (168)
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
$906 SGD
Show price breakdown
for 5 nights
$906 SGD 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
,
·
3 bathrooms
3 bathrooms
5–10 Sept
5–10 Sept
$3,776 SGD
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for 5 nights
$3,776 SGD for 5 nights
4.88 out of 5 average rating, 17 reviews
4.88 (17)
Room in Cummington
Singing Bridge Turquoise Room (single room)
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
8–13 Sept
8–13 Sept
$618 SGD
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for 5 nights
$618 SGD for 5 nights
4.72 out of 5 average rating, 95 reviews
4.72 (95)
Top guest favourite
Guest favourite
Home in Hinsdale
Berkshire Cabin by Lake Ashmere
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$1,856 SGD
$1,483 SGD
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for 5 nights
5.0 out of 5 average rating, 30 reviews
5.0 (30)
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
Show price breakdown
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
Chalet in Peru
Swiss Chalet Style Timberframe Home in Berkshires
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$2,146 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 Windsor
Beautiful Log Cabin with a Mountain View
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
6–11 Sept
6–11 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)
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
$2,178 SGD
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for 5 nights
$2,178 SGD for 5 nights
4.93 out of 5 average rating, 139 reviews
4.93 (139)
Top guest favourite
Guest favourite
Flat in Plainfield
Sunny carriage house apartment
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
21–26 Sept
21–26 Sept
$1,134 SGD
$1,004 SGD
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for 5 nights
Free cancellation
4.95 out of 5 average rating, 304 reviews
4.95 (304)
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
$12,855 SGD
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for 5 nights
$12,855 SGD for 5 nights
5.0 out of 5 average rating, 23 reviews
5.0 (23)
Guest favourite
Guest favourite
Room in Dalton
Mother in Law unit in Dalton
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$715 SGD
$563 SGD
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for 5 nights
4.93 out of 5 average rating, 174 reviews
4.93 (174)
Guest favourite
Guest favourite
Cottage in Hinsdale
Lake Escape in the Berkshires
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
26–31 May
26–31 May
$1,708 SGD
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for 5 nights
$1,708 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 60 reviews
4.92 (60)
Guest favourite
Guest favourite
Home in Worthington
Berkshires Carriage House - Artist's Loft, Retreat
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$1,460 SGD
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for 5 nights
$1,460 SGD for 5 nights
4.98 out of 5 average rating, 45 reviews
4.98 (45)
Guest favourite
Guest favourite
Home in Hinsdale
Modern Lake Cottage - 3 minute walk to beach
2 bedrooms
2 bedrooms
,
·
2 king beds
2 king beds
,
·
2 bathrooms
2 bathrooms
30 Sept – 5 Oct
30 Sept – 5 Oct
$2,692 SGD
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for 5 nights
$2,692 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
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$1,658 SGD
$1,445 SGD
Show price breakdown
for 5 nights
Free cancellation
4.55 out of 5 average rating, 38 reviews
4.55 (38)
Guest favourite
Guest favourite
Home in Cheshire
Cheshire Cove | Waterfront • Kayak • Firepit
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
21–26 Sept
21–26 Sept
$2,551 SGD
$2,025 SGD
Show price breakdown
for 5 nights
4.88 out of 5 average rating, 32 reviews
4.88 (32)
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