Cornish-Windsor Covered Bridge

Windsor Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Windsor holiday rentals

Aerial view

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (25 reviews)
"I enjoy the location "
United States
troy
The price is RM246
RM848 total
includes taxes & fees
28 Jun - 29 Jun
Mountain Green
Interior

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is RM1,054
RM1,838 total
includes taxes & fees
27 Jul - 28 Jul
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
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 RM756
RM1,231 total
includes taxes & fees
29 Jun - 30 Jun
Brook Road Cabin
Interior

Trail Creek 05

Trail Creek 05
3.5 star property
Killington
10.0 out of 10, Exceptional, (2 reviews)
"I ended up getting changed to another property trail creek 80. I wish I could give 10 stars! This place is amazing! Clean quiet spacious and so much more. I want to already book this same place for next years Spartan race!! Thank you for having an amazing property "
United States
Kimberly
The price is RM706
RM1,669 total
includes taxes & fees
27 Jun - 28 Jun
Trail Creek 05
Marina

Okemo Westwood Condo 3 Bedroom Condo by RedAwning

Okemo Westwood Condo 3 Bedroom Condo by RedAwning
3.5 star property
Ludlow
The price is RM703
RM3,433 total
includes taxes & fees
28 Jun - 29 Jun
Okemo Westwood Condo 3 Bedroom Condo by RedAwning
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 RM4,785
RM7,605 total
includes taxes & fees
30 Jun - 1 Jul
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
Interior

Pinnacle C16

Pinnacle C16
3.0 star property
Killington
8.8 out of 10, Excellent, (3 reviews)
"Ski trip - warm, cozy, quiet, 2 min ride on free shuttle bus to base."
United States
Steve
Pinnacle C16
Interior

Pinnacle E15

Pinnacle E15
3.5 star property
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Great location and close to restaurants in Killington. "
United States
Kevin
The price is RM452
RM1,380 total
includes taxes & fees
27 Jun - 28 Jun
Pinnacle E15
Interior

Colony Club C12

Colony Club C12
3.5 star property
Killington
The price is RM1,011
RM2,710 total
includes taxes & fees
27 Jun - 28 Jun
Colony Club C12
Interior

Hemlock Ridge 6A

Hemlock Ridge 6A
3.5 star property
Killington
8.0 out of 10, Very good, (1 review)
"Everything was good except minor confusion with the lock code. But response was quick, and the issue was resolved."
United States
Leonid
The price is RM1,011
RM2,544 total
includes taxes & fees
27 Jun - 28 Jun
Hemlock Ridge 6A
Property grounds

Whiffletree C2

Whiffletree C2
3.5 star property
Killington
4.0 out of 10, (1 review)
"It would be good if they informed you that the unit is a walkout basement unit. Also out key code did not work when we arrived. Answering service gave us the cleaning peoples code that only worked once. day 2 we had to call and get a third code. "
United States
Gregory
The price is RM624
RM1,716 total
includes taxes & fees
27 Jun - 28 Jun
Whiffletree C2
Pool

Pinnacle F21

Pinnacle F21
3.5 star property
Killington
The price is RM783
RM2,243 total
includes taxes & fees
27 Jun - 28 Jun
Pinnacle F21
Living area

Blue Haven 3 Bedroom Home

Blue Haven 3 Bedroom Home
3.0 star property
Killington
The price is RM1,793
RM4,473 total
includes taxes & fees
30 Jun - 1 Jul
Blue Haven 3 Bedroom Home
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 staff went out of their way to make our stay enjoyable!"
Jean-Pierre 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 11 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 Brownsville Trail.

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.