Windsor Vacation Rentals

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Tonight
Nov 5 - Nov 6
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Nov 6 - Nov 7
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Nov 7 - Nov 9
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Nov 14 - Nov 16

Vacation Rentals in Windsor

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Vacation Village in the Berkshires
Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2123)
"Good location; reasonable price; very clean and quiet - would definitely return"
United States
Steven
The price is NT$2,828
NT$3,496 total
includes taxes & fees
Nov 12 - Nov 13
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (984)
"It was a fun place to stay. Rooms were clean and dishes well stocked in the kitchenette. "
United States
Sandhya
The price is NT$4,593
NT$5,130 total
includes taxes & fees
Nov 7 - Nov 8
Jiminy Peak Mountain Resort
Exterior
Huttopia Berkshires
Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
Huttopia Berkshires
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow
The Ponds at Foxhollow
3.0 star property
8.6 out of 10, Excellent, (132)
"Perfect location "
United States
krystle
The price is NT$4,377
NT$4,889 total
includes taxes & fees
Dec 5 - Dec 6
The Ponds at Foxhollow
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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Top Windsor Hotel Reviews

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Everything was fine just no shampoo in the dispencer"
Svetlana 1-night trip
Posted 2 days ago
Best Western Plus Berkshire Hills Inn & Suites

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, there are vacation rentals close to well known attractions in Windsor, or you can select a more secluded option if you'd like a relaxing place to stay. Windsor is known for its restaurants and shopping.

What can I see and do in Windsor?

Explore the area and family-friendly sights such as Berkshire Museum, or get out into nature at a spot like Mount Greylock State Reservation Visitor Center. Mount Greylock and Barrington Stage Company are a couple of places you'll find in the larger area.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Windsor. Vacation rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for family gatherings.