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7 Dec - 8 Dec
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8 Dec - 9 Dec
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12 Dec - 14 Dec
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19 Dec - 21 Dec

Top Holiday Rentals in Windsor

Exterior
Brook Road Cabin

Cottage in Goshen

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
House (2 Bedrooms) | Interior
Ludlow Ski Cabin 2 Mi to Ski Parking

Cottage in Ludlow

3.0 star property
The price is ₹16,469
₹32,950 total
includes taxes & fees
8 Dec - 9 Dec
Ludlow Ski Cabin 2 Mi to Ski Parking
Condo, 1 Bedroom | Exterior
Mountain Green Resort by Killington VR - 1 Bedrooms

Condo in Killington

3.5 star property
The price is ₹12,689
₹40,954 total
includes taxes & fees
8 Dec - 9 Dec
Mountain Green Resort by Killington VR - 1 Bedrooms
Condo, 1 Bedroom, Kitchen, Garden View | Terrace/patio
The Suites at Killington Center

Condo in Killington

3.5 star property
The price is ₹10,007
₹30,806 total
includes taxes & fees
10 Dec - 11 Dec
The Suites at Killington Center
Indoor pool
Mountain Green

Condo resort in Killington

2.0 star property
7.0 out of 10, Good, (15)
"Great communication from Jeff."
United States
Dennis
The price is ₹17,819
₹23,904 total
includes taxes & fees
8 Dec - 9 Dec
Mountain Green
Comfort Townhome | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Brook Road Condo

Holiday Home in Goshen

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 ₹15,479
₹25,777 total
includes taxes & fees
8 Dec - 9 Dec
Brook Road Condo
Condo, 2 Bedrooms | Exterior
Fall Line Condos by Killington VR - 2 Bedrooms

Condo in Killington

3.5 star property
The price is ₹13,659
₹49,681 total
includes taxes & fees
8 Dec - 9 Dec
Fall Line Condos by Killington VR - 2 Bedrooms
Studio | Exterior
Fall Line Small Studio - Perfect For Two - On Shuttle Route W/ Amenities G6a 1 Bedroom Condo

Condo in Killington

2.0 star property
The price is ₹10,590
₹26,390 total
includes taxes & fees
8 Dec - 9 Dec
Fall Line Small Studio - Perfect For Two - On Shuttle Route W/ Amenities G6a 1 Bedroom Condo
Condo, 2 Bedrooms | Sauna
Fall Line Condo D4 2 Bedroom Condo

Condo in Killington

3.5 star property
10.0 out of 10, Exceptional, (1)
"Super condo à proximité de la montagne de ski Killington. "
Canada
catherine
The price is ₹17,801
₹50,641 total
includes taxes & fees
8 Dec - 9 Dec
Fall Line Condo D4 2 Bedroom Condo
Condo, 2 Bedrooms | Dining
The Woods by Killington Vacation Rentals - 2 Bedrooms

Condo in The Woods

3.0 star property
10.0 out of 10, Exceptional, (2)
"The condo had everything we needed for a comfortable and enjoyable stay. The pool and hot tub area were great additions. We would definitely stay again."
United States
Paul
The price is ₹17,610
₹56,757 total
includes taxes & fees
9 Dec - 10 Dec
The Woods by Killington Vacation Rentals - 2 Bedrooms
Condo, 4 Bedrooms | Dining
Sunrise Bear Ridge C4 4 Bedroom Condo

Condo in Killington

3.0 star property
The price is ₹22,426
₹68,954 total
includes taxes & fees
8 Dec - 9 Dec
Sunrise Bear Ridge C4 4 Bedroom Condo
Condo, 3 Bedrooms | Exterior
Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo

Condo in Killington

2.0 star property
The price is ₹18,168
₹63,080 total
includes taxes & fees
8 Dec - 9 Dec
Sunrise West Glade: 3br, 3ba Ski In/ski Out Condo 3 Bedroom Condo
Condo, 3 Bedrooms | Private kitchen
Hemlock Ridge 2b: Charming Two Floor Condo In The Heart Of Killington. Perfect! 3 Bedroom Condo

Condo in Killington

2.0 star property
The price is ₹16,822
₹58,821 total
includes taxes & fees
8 Dec - 9 Dec
Hemlock Ridge 2b: Charming Two Floor Condo In The Heart Of Killington. Perfect! 3 Bedroom Condo
Condo, 3 Bedrooms | 3 bedrooms, free WiFi
Northbrook Condo 3 Bedroom Condo

Condo in Killington

3.0 star property
The price is ₹19,268
₹62,443 total
includes taxes & fees
8 Dec - 9 Dec
Northbrook Condo 3 Bedroom Condo
House, 3 Bedrooms | Living area
The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home

Holiday Home in Killington

3.0 star property
The price is ₹26,359
₹80,096 total
includes taxes & fees
8 Dec - 9 Dec
The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home
Condo, 1 Bedroom | Private kitchen
Mountain Green Condo 1c7 1 Bedroom Condo

Condo in Killington

2.0 star property
The price is ₹15,257
₹43,671 total
includes taxes & fees
8 Dec - 9 Dec
Mountain Green Condo 1c7 1 Bedroom Condo
Condo, 3 Bedrooms | Living area
Whiffletree I5 3 Bedroom Condo

Condo in Killington

3.0 star property
The price is ₹20,245
₹59,345 total
includes taxes & fees
8 Dec - 9 Dec
Whiffletree I5 3 Bedroom Condo
House, 6 Bedrooms | Private kitchen
Breakaway House by Killington Vacation Rentals

Holiday Home in Killington

2.0 star property
The price is ₹18,168
₹65,562 total
includes taxes & fees
8 Dec - 9 Dec
Breakaway House by Killington Vacation Rentals
Condo, 2 Bedrooms | Interior
Skiers! Fox Hollow 2br/2ba Condo. Across From Pico, Minutes To Killington 2 Bedroom Condo

Condo in Rutland

2.0 star property
The price is ₹13,522
₹49,050 total
includes taxes & fees
8 Dec - 9 Dec
Skiers! Fox Hollow 2br/2ba Condo. Across From Pico, Minutes To Killington 2 Bedroom Condo
House, 4 Bedrooms | Outdoor spa tub
Whitetail Chalet 4 Bedroom Home

Holiday Home in Killington

3.0 star property
The price is ₹23,537
₹71,407 total
includes taxes & fees
8 Dec - 9 Dec
Whitetail Chalet 4 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

Hilton Garden Inn Hanover Lebanon

Hilton Garden Inn Hanover Lebanon

10/10 Excellent
"We loved our stay at this pretty property. It was super clean, inviting and the staff was great. They went above and beyond with a special room request that we really appreciated. I'd for sure stay again! Thanks to the staff for that request :) "
Keleigh 2-night trip
Posted 2 days ago
Hilton Garden Inn Hanover Lebanon

Find out more about Windsor

Holiday Rentals in 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!

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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.