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Tonight
25 Oct - 26 Oct
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26 Oct - 27 Oct
Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov

Top Holiday Rentals in Windsor

Comfort Townhome | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Brook Road Condo
Brook Road Condo
3.0 star property
8.8 out of 10, Excellent, (3)
"Convenient location, quiet and rural. Accommodations were clean and neat. Nice to have full kitchen for meal prep and snacks."
United States
Margaret
The price is ฿5,625
฿9,368 total
includes taxes & fees
9 Nov - 10 Nov
Brook Road Condo
Condo, 1 Bedroom, Kitchen, Garden View | Private kitchen | Mini-fridge, microwave, oven, cookware/dishes/utensils
The Suites at Killington Center
The Suites at Killington Center
3.5 star property
The price is ฿4,364
฿18,582 total
includes taxes & fees
28 Oct - 29 Oct
The Suites at Killington Center
Condo, 3 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster
Okemo Westwood Condo 3 Bedroom Condo by RedAwning
Okemo Westwood Condo 3 Bedroom Condo by RedAwning
3.5 star property
Okemo Westwood Condo 3 Bedroom Condo by RedAwning
Indoor pool
Mountain Green
Mountain Green
2.0 star property
6.6 out of 10, (13)
"Great communication from Jeff."
United States
Dennis
The price is ฿6,541
฿8,775 total
includes taxes & fees
28 Oct - 29 Oct
Mountain Green
Exterior
Brook Road Cabin
Brook Road Cabin
3.5 star property
7.8 out of 10, Good, (9)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
United States
Jill
Brook Road Cabin
House, 3 Bedrooms | Living area
Breakaway House by Killington Vacation Rentals
Breakaway House by Killington Vacation Rentals
2.0 star property
The price is ฿6,669
฿23,915 total
includes taxes & fees
27 Oct - 28 Oct
Breakaway House by Killington Vacation Rentals
Studio | Property grounds
New Killington Studio W/ Kitchenette, Wifi, Tv, Fireplace. Close To Resort On The Shuttle Route. 213 1 Bedroom Condo
New Killington Studio W/ Kitchenette, Wifi, Tv, Fireplace. Close To Resort On The Shuttle Route. 213 1 Bedroom Condo
3.5 star property
The price is ฿8,420
฿17,204 total
includes taxes & fees
14 Nov - 15 Nov
New Killington Studio W/ Kitchenette, Wifi, Tv, Fireplace. Close To Resort On The Shuttle Route. 213 1 Bedroom Condo
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

Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"Great value-clean, quiet, safe and good price. Breakfast was basic."
Mark 1-night trip
Posted 13 hours ago
Align Inn Vermont

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 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.

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 10 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.