Windsor Vacation Rentals

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Nov 28 - Nov 29
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Nov 29 - Nov 30
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Nov 28 - Nov 30
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Dec 5 - Dec 7

Vacation Rentals in Windsor

Lobby
Vacation Village in the Berkshires

Condo in Williamstown

3.0 star property
8.8 out of 10, Excellent, (2149)
"Great place!"
United States
Nicole
The price is ₩108,297
₩137,011 total
includes taxes & fees
Nov 29 - Nov 30
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

3.0 star property
8.2 out of 10, Very Good, (986)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
The price is ₩217,905
₩243,399 total
includes taxes & fees
Nov 30 - Dec 1
Jiminy Peak Mountain Resort
Exterior
Huttopia Berkshires

Camping in Williamstown

1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is ₩248,763
₩277,868 total
includes taxes & fees
Dec 16 - Dec 17
Huttopia Berkshires
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

Condo resort in Lenox

3.0 star property
8.6 out of 10, Excellent, (134)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The price is ₩186,145
₩207,924 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
"We stay here every Thanksgiving week and it is always a pleasure with the friendly staff, nice clean and orderly room and great breakfast. It is top rate."
James 1-night trip
Posted 17 hours ago
Best Western Plus Berkshire Hills Inn & Suites

Find out more about Windsor

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

  • View our selection of featured Vacation rentals in Windsor
  • Use the map to find apartments and other Vacation homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation 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 Wahconah Falls State Park. Crane Museum of Papermaking and Mount Greylock State Reservation Visitor Center 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.