Photo by William E Berry Jr.

Windsor Holiday Rentals

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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec

Holiday Rentals in Windsor

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (49)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Mountain Green
Indoor pool

Mountain Green

2.0 star property
6.2 out of 10, (12)
"The condo was very cozy for a family of four and suited us perfectly. Beds were comfortable and condo was clean. "
The price is S$299
includes taxes & fees
28 Sept - 29 Sept
Mountain Green
Winterplace at Okemo
Property grounds

Winterplace at Okemo

4.0 star property
8.8 out of 10, Excellent, (24)
"I love everything about staying here!! The front desk are so nice and welcoming!! I really appreciate and recommend this place "
Winterplace at Okemo
Okemo Mountain Lodging
Exterior

Okemo Mountain Lodging

3.5 star property
7.8 out of 10, Good, (28)
"I had an amazing time with my family, I will definitely be coming back "
Okemo Mountain Lodging
Solitude Village at Okemo
Private kitchen

Solitude Village at Okemo

4.0 star property
8.2 out of 10, Very good, (29)
"Beautiful Area. "
Solitude Village at Okemo
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

Super 8 by Wyndham White River Junction

Super 8 by Wyndham White River Junction

10/10 Excellent
"The most important two things to me Cleanliness A comfortable mattress to sleep on"
Kathleen 1-night trip
Posted 19 hours ago
Super 8 by Wyndham White River Junction

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals in Windsor close to Path of Life Garden, or you can select a more secluded option if you're looking for a relaxing stay. Windsor is known for its breweries and golf courses. Make sure you have time to check out the forests while you're in the area.

How many holiday rentals are there in Windsor?

With 9 Expedia holiday rentals, you're guaranteed to find just the right place for your Windsor stay.

What can I see and do in Windsor?

Connecticut River and Path of Life Garden are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include The Sustainable Farmer. Other places in town to visit include Harpoon Brewery and Mt Ascutney State Park.

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 feature amenities such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.