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Windsor Vacation Rentals

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Check prices for these dates

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

Our top choices for Windsor holiday rentals

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
Private kitchen
Brook Road Condo

Holiday 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 RM745
RM1,212 total
includes taxes & fees
8 Jan - 9 Jan 2026
Brook Road Condo
Exterior
Killington Ski Resort VT Vacation Condos

Condo in Killington

Killington Ski Resort VT Vacation Condos
3.5 star property
The price is RM858
RM1,717 total
includes taxes & fees
21 Jan - 22 Jan 2026
Killington Ski Resort VT Vacation Condos
Indoor pool
Mountain Green

Condo resort in Killington

Mountain Green
2.0 star property
6.8 out of 10, (16)
"Great communication from Jeff."
United States
Dennis
The price is RM963
RM1,292 total
includes taxes & fees
12 Jan - 13 Jan 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

Après Inn Killington

Après Inn Killington

10/10 Excellent
"Apres Inn was exactly what we wanted for a ski vacation at Killington. No frills, but they do provide coffee, microwave and a mini fridge. The Inn has been recently renovated and was impeccably clean. The beds were comfortable. The bonus is that it is less than 10 minutes to the slope. We will absolutely book with them again when we come back. "
Andrew 3-night trip
Posted 3 days ago
Après Inn Killington

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia.co.uk! 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 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.

How many holiday rentals are there in Windsor?

With 12 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.