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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
$1,885 SGD
$1,666 SGD
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for 5 nights
,
·
4.88 out of 5 average rating, 32 reviews
4.88 (32)
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
$910 SGD
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for 5 nights
$910 SGD for 5 nights
4.8 out of 5 average rating, 41 reviews
4.8 (41)
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
$1,664 SGD
$1,450 SGD
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for 5 nights
Free cancellation
4.7 out of 5 average rating, 99 reviews
4.7 (99)
Home in Cummington
Berkshire Hills Nature Lovers' Log Home Retreat
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
3–8 Sept
3–8 Sept
$4,015 SGD
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for 5 nights
$4,015 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
$734 SGD
$645 SGD
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for 5 nights
4.72 out of 5 average rating, 95 reviews
4.72 (95)
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
$1,761 SGD
Show price breakdown
for 5 nights
$1,761 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 168 reviews
4.99 (168)
Top guest favourite
Guest favourite
Home in Hinsdale
Berkshire Lake-side Retreat
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
7–12 Sept
7–12 Sept
$2,199 SGD
$1,964 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 17 reviews
5.0 (17)
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
$1,761 SGD
Show price breakdown
for 5 nights
$1,761 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 88 reviews
4.94 (88)
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
$1,874 SGD
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for 5 nights
$1,874 SGD for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Top guest favourite
Guest favourite
Home in Dalton
Brooksong, the perfect Berkshires getaway
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
,
·
2.5 bathrooms
2.5 bathrooms
9–14 Sept
9–14 Sept
$3,972 SGD
$3,489 SGD
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for 5 nights
4.93 out of 5 average rating, 211 reviews
4.93 (211)
Guest favourite
Guest favourite
Home in Cheshire
Large Secluded Berkshire Home
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
3–8 Sept
3–8 Sept
$3,040 SGD
$2,696 SGD
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for 5 nights
4.81 out of 5 average rating, 165 reviews
4.81 (165)
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
$2,230 SGD
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for 5 nights
$2,230 SGD for 5 nights
4.93 out of 5 average rating, 139 reviews
4.93 (139)
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
$2,154 SGD
$1,894 SGD
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for 5 nights
Free cancellation
4.93 out of 5 average rating, 311 reviews
4.93 (311)
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
3–8 Sept
3–8 Sept
$3,086 SGD
$2,716 SGD
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for 5 nights
5.0 out of 5 average rating, 20 reviews
5.0 (20)
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
$718 SGD
$629 SGD
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for 5 nights
4.93 out of 5 average rating, 174 reviews
4.93 (174)
Guest favourite
Guest favourite
Cabin in Hinsdale
Relaxing Berkshire cabin on Lake Ashmere
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
3–8 Sept
3–8 Sept
$2,032 SGD
$1,670 SGD
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for 5 nights
4.96 out of 5 average rating, 50 reviews
4.96 (50)
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
$1,138 SGD
$1,002 SGD
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for 5 nights
Free cancellation
4.95 out of 5 average rating, 303 reviews
4.95 (303)
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
$12,901 SGD
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for 5 nights
$12,901 SGD for 5 nights
5.0 out of 5 average rating, 23 reviews
5.0 (23)
Top guest favourite
Guest favourite
Home in Lanesborough
The Pond House
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
20–25 Nov
20–25 Nov
$1,847 SGD
Show price breakdown
for 5 nights
$1,847 SGD for 5 nights
Free cancellation
4.96 out of 5 average rating, 55 reviews
4.96 (55)
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