Windsor Vacation Rentals

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Windsor holiday rentals

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
Brook Road Cabin
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 RM2,698
RM6,209 total
includes taxes & fees
12 Feb - 13 Feb
Okemo Westwood Condo 3 Bedroom Condo by RedAwning
Aerial view

Mountain Green

Mountain Green
2.0 star property
Killington
7.0 out of 10, Good, (19 reviews)
"Great !"
United States
Raul
The price is RM786
RM1,054 total
includes taxes & fees
10 Feb - 11 Feb
Mountain Green
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
The price is RM730
RM1,325 total
includes taxes & fees
11 Feb - 12 Feb
Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country
Aerial view

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is RM1,567
RM2,592 total
includes taxes & fees
22 Feb - 23 Feb
The Suites at Killington Center
Restaurant

Mountain Green Resort

Mountain Green Resort
4.0 star property
Killington
4.0 out of 10, (2 reviews)
"Clean room, elevator broken and not enough bathroom towels."
United States
Jing
The price is RM2,644
RM4,109 total
includes taxes & fees
12 Feb - 13 Feb
Mountain Green Resort
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 RM726
RM1,182 total
includes taxes & fees
10 Feb - 11 Feb
Brook Road Condo
Exterior

Fall Line Condos by Killington VR - 2 Bedrooms

Fall Line Condos by Killington VR - 2 Bedrooms
3.5 star property
Killington
The price is RM1,678
RM3,836 total
includes taxes & fees
26 Feb - 27 Feb
Fall Line Condos by Killington VR - 2 Bedrooms
Interior

Mountain Green 3G6

Mountain Green 3G6
3.0 star property
Killington
The price is RM3,301
RM4,949 total
includes taxes & fees
12 Feb - 13 Feb
Mountain Green 3G6
Interior

Mountain Green Resort by Killington VR - 1 Bedrooms

Mountain Green Resort by Killington VR - 1 Bedrooms
3.5 star property
Killington
8.0 out of 10, Very good, (1 review)
"I had trouble getting in and out of the inner roads around the buildings and had to wait to use my rental car until the bus traffic cleared Old Mill Rd. to slush. This made me kind of locked in, but the bus service to and from the ski lodges did make it possible to ski. And that was the main reason I stayed at Mountain Green Resort the proximity and shuttle service."
United States
Scott
The price is RM1,861
RM3,746 total
includes taxes & fees
16 Feb - 17 Feb
Mountain Green Resort by Killington VR - 1 Bedrooms
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
Interior

Fall Line Condo B7 1 Bedroom Home

Fall Line Condo B7 1 Bedroom Home
3.5 star property
Killington
The price is RM1,365
RM2,988 total
includes taxes & fees
22 Feb - 23 Feb
Fall Line Condo B7 1 Bedroom Home
Exterior

Fall Line Condos by Killington VR - 1 Bedrooms

Fall Line Condos by Killington VR - 1 Bedrooms
3.5 star property
Killington
The price is RM1,300
RM2,957 total
includes taxes & fees
22 Feb - 23 Feb
Fall Line Condos by Killington VR - 1 Bedrooms
Dining

Fall Line Condo E1 1 Bedroom Condo

Fall Line Condo E1 1 Bedroom Condo
3.5 star property
Killington
The price is RM2,235
RM4,174 total
includes taxes & fees
18 Feb - 19 Feb
Fall Line Condo E1 1 Bedroom Condo
Sauna

Fall Line Condos by Killington VR - Studios

Fall Line Condos by Killington VR - Studios
2.0 star property
Killington
7.0 out of 10, Good, (2 reviews)
"Yes by a shuttle very easy"
United States
Philip
The price is RM1,370
RM2,507 total
includes taxes & fees
17 Feb - 18 Feb
Fall Line Condos by Killington VR - Studios
Sauna

Sunrise Bear Ridge C4 4 Bedroom Condo

Sunrise Bear Ridge C4 4 Bedroom Condo
3.0 star property
Killington
The price is RM2,883
RM5,809 total
includes taxes & fees
25 Feb - 26 Feb
Sunrise Bear Ridge C4 4 Bedroom Condo
Living area

Shreadquarters 3 Bedroom Home

Shreadquarters 3 Bedroom Home
3.0 star property
Killington
The price is RM2,575
RM5,274 total
includes taxes & fees
23 Feb - 24 Feb
Shreadquarters 3 Bedroom Home
Living area

The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home

The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home
3.0 star property
Killington
The price is RM4,487
RM8,426 total
includes taxes & fees
17 Feb - 18 Feb
The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home
View from property

Whiffletree I5 3 Bedroom Condo

Whiffletree I5 3 Bedroom Condo
3.0 star property
Killington
The price is RM3,380
RM6,170 total
includes taxes & fees
18 Feb - 19 Feb
Whiffletree I5 3 Bedroom Condo
Exterior

Mountain Green Resort by Killington VR - 2 Bedrooms

Mountain Green Resort by Killington VR - 2 Bedrooms
2.0 star property
Killington
The price is RM1,288
RM3,286 total
includes taxes & fees
5 Mar - 6 Mar
Mountain Green Resort by Killington VR - 2 Bedrooms
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

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Friendly greeting upon arrival. The 3 bedroom villa met all of our needs and expectations. "
Nancy 1-night trip
Posted 1 day ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

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.