Photo by William E Berry Jr.

Windsor Holiday Rentals

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Check prices for these dates

Tonight
5 Jun - 6 Jun
Tomorrow
6 Jun - 7 Jun
This weekend
6 Jun - 8 Jun
Next weekend
13 Jun - 15 Jun

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, (43)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Okemo Mountain Lodging
Exterior

Okemo Mountain Lodging

3.5 star property
7.8 out of 10, Good, (27)
"We are so impressed with the lodging. We will definitely be back. "
Okemo Mountain Lodging
Solitude Village at Okemo
Private kitchen

Solitude Village at Okemo

4.0 star property
8.0 out of 10, Very good, (25)
"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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Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals in Windsor close to The Sustainable Farmer, 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.

What are some of the best holiday rentals that Windsor has to offer?

Okemo Mountain Lodging: This holiday home rental outside Windsor is in the mountains, and equipped with daily housekeeping and an LCD TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop.

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 Paradise Park 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 American Precision Museum and Harpoon Brewery.

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.