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Top Holiday Rentals in Windsor

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (2041)
"Extended stay since resort was so beautiful"
The price is Rp1.521.127
Rp1.881.014 total
includes taxes & fees
2 Nov - 3 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (981)
"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."
The price is Rp2.470.867
Rp2.759.959 total
includes taxes & fees
19 Oct - 20 Oct
Jiminy Peak Mountain Resort
Huttopia Berkshires
Restaurant

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is Rp1.623.174
Rp1.813.085 total
includes taxes & fees
9 Oct - 10 Oct
Huttopia Berkshires
The Ponds at Foxhollow
Indoor pool, outdoor pool, pool umbrellas, pool loungers

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (131)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Great lodge with 1 bedroom suites and fully stocked kitchens "
Thomas 5-night trip
Posted 8 hours ago
Berkshire Mountain Lodge

Find out more about Windsor

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia.co.id! 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 holiday rental in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing 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 wider area.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.