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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Windsor vacation rentals

Comfort Townhome | Private kitchen | Full-size fridge, microwave, oven, stovetop
Brook Road Condo

Vacation Home in Goshen

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 ₩265,265
₩431,720 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Brook Road Condo
Exterior
Brook Road Cabin

Cottage in Goshen

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
Restaurant
Mountain Green Resort

Apartment in Killington

Mountain Green Resort
4.0 star property
6.0 out of 10, (1)
"Clean room, elevator broken and not enough bathroom towels."
United States
Jing
The price is ₩814,250
₩1,334,157 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Mountain Green Resort
Condo, 1 Bedroom, Kitchen, Garden View | Terrace/patio
The Suites at Killington Center

Condo in Killington

The Suites at Killington Center
3.5 star property
The price is ₩297,558
₩644,479 total
includes taxes & fees
Jan 14 - Jan 15, 2026
The Suites at Killington Center
Indoor pool
Mountain Green

Condo resort in Killington

Mountain Green
2.0 star property
6.8 out of 10, (17)
"Great communication from Jeff."
United States
Dennis
The price is ₩333,023
₩446,734 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Mountain Green
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

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"The best thing about this place is location and the shuttle to the mountain. Onsite restaurant was good as well but with basic food. While there is nothing bad, there is nothing remarkable either to justify the cost. Some things to point out: Rooms were not made for the entire stay. Breakfast was just costco pastries and bagels... Heated pool (while nice) was not quite hot enough given the outdoor temps. (other places much better) ALSO! This one is important - if you dont take your key you cant get back in from the pool even though its fenced in! DANGEROUS! you can freeze to death trying to yell for help....Thank god I took my card and phone! Verdict: Overall a nice place but very overpriced. "
Alexander 3-night trip
Posted 5 hours ago
The Mountain Inn at Killington

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, we offer vacation rentals in Windsor close to The Sustainable Farmer, or you can select a more secluded option if you're looking for extra privacy while you relax. 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 vacation rentals are there in Windsor?

With 12 Expedia vacation rentals, you're sure 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 vacation rentals like in Windsor?

Vacation rentals are private properties you can stay in for several days or more in Windsor. Vacation rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for family gatherings.