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Compare 274 Vacation Homes in Windsor with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (241)
The price is AED 551
AED 837 total
includes taxes & fees
7 Apr - 8 Apr

Hancock Village Inn at Jiminy Peak
Hancock Village Inn at Jiminy Peak
9.8 out of 10, Exceptional, (10)
The price is AED 2,017
AED 3,801 total
includes taxes & fees
11 Apr - 12 Apr

1810 Brook Side Mill/House / EV Level 2 Charging on Site
1810 Brook Side Mill/House / EV Level 2 Charging on Site
10.0 out of 10, Exceptional, (71)

Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (212)

Heart of Lenox Walk to Town Cozy Cottage!
Heart of Lenox Walk to Town Cozy Cottage!
10.0 out of 10, Exceptional, (70)

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
10.0 out of 10, Exceptional, (3)

Hilltown Nest is a wonderful place for family and friends to gather.
Hilltown Nest is a wonderful place for family and friends to gather.
9.8 out of 10, Exceptional, (15)

Mountain Blossom Retreat by Evergreen Home
Mountain Blossom Retreat by Evergreen Home
10.0 out of 10, Exceptional, (5)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Windsor

Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1794)
The price is AED 380
AED 458 total
includes taxes & fees
16 Apr - 17 Apr

Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very Good, (926)
The price is AED 493
AED 540 total
includes taxes & fees
7 Apr - 8 Apr

Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (241)
The price is AED 551
AED 837 total
includes taxes & fees
7 Apr - 8 Apr
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Recent reviews of Windsor hotels
Recent reviews of Windsor hotels

Life House Berkshires
5/5 Excellent
"Quiet, quick, and easy stay. Clean simple rooms "
A verified traveler stayed at Life House Berkshires
Posted 17 hours ago
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