Windsor Vacation Rentals

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Windsor holiday rentals

Aerial view

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is RM383
RM1,293 total
includes taxes & fees
30 Mar - 31 Mar
The Suites at Killington Center
Living room

Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
7.8 out of 10, Good, (9 reviews)
"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
The price is RM728
RM1,185 total
includes taxes & fees
29 Mar - 30 Mar
Brook Road Cabin
Exterior

Okemo Mountain Lodging by Vail Resorts

Okemo Mountain Lodging by Vail Resorts
3.5 star property
Clock Tower Base Area
7.8 out of 10, Good, (28 reviews)
"I had an amazing time with my family, I will definitely be coming back "
United States
Yenifer
The price is RM5,934
RM7,549 total
includes taxes & fees
28 Mar - 29 Mar
Okemo Mountain Lodging by Vail Resorts
Interior

Killington Center 531

Killington Center 531
3.5 star property
Killington
The price is RM542
RM1,118 total
includes taxes & fees
30 Mar - 31 Mar
Killington Center 531
Front of property

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is RM4,355
RM6,774 total
includes taxes & fees
29 Mar - 30 Mar
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
Aerial view

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (23 reviews)
"I enjoy the location "
United States
troy
The price is RM797
RM1,069 total
includes taxes & fees
9 Apr - 10 Apr
Mountain Green
Living area

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
Breakaway House by Killington Vacation Rentals
In-room dining

Brook Road Condo

Brook Road Condo
3.0 star property
Goshen
8.8 out of 10, Excellent, (3 reviews)
"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 RM728
RM1,185 total
includes taxes & fees
1 Apr - 2 Apr
Brook Road Condo
Interior

Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country

Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country
2.0 star property
Killington
Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country
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

8/10 Good
"Staff was helpful. Shuttle was easy to use. Breakfast options were good. Would’ve liked non dairy milk options besides oat milk (soy or almond milk would be helpful for allergies). We arrived after 9 so everything was shut down. Limited food options so eat on your way or arrive early. "
Karen 1-night trip
Posted 1 hour ago
The Mountain Inn at 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 Maze of Adventure, 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 scenic spots to enjoy the outdoors, whereas American Precision Museum is one of the cultural attractions. 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.