Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Windsor vacation 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
Aerial view

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (20 reviews)
"Great !"
United States
Raul
The price is P12,476
P16,736 total
includes taxes & fees
Mar 11 - Mar 12
Mountain Green
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 P18,771
P48,078 total
includes taxes & fees
Mar 5 - Mar 6
Mountain Green Resort by Killington VR - 2 Bedrooms
Aerial view

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is P11,373
P25,277 total
includes taxes & fees
Feb 22 - Feb 23
The Suites at Killington Center
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 P28,782
P39,321 total
includes taxes & fees
Feb 19 - Feb 20
Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country
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 P10,677
P17,377 total
includes taxes & fees
Feb 22 - Feb 23
Brook Road Condo
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 P45,068
P94,442 total
includes taxes & fees
Feb 17 - Feb 18
The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home
Interior

Killington Center 531

Killington Center 531
3.5 star property
Killington
Killington Center 531
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 P24,266
P55,815 total
includes taxes & fees
Feb 18 - Feb 19
Fall Line Condos by Killington VR - 2 Bedrooms
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 P19,979
P44,685 total
includes taxes & fees
Feb 22 - Feb 23
Fall Line Condos by Killington VR - 1 Bedrooms
Interior

Fall Line Condo B7 1 Bedroom Home

Fall Line Condo B7 1 Bedroom Home
3.5 star property
Killington
The price is P19,423
P43,048 total
includes taxes & fees
Feb 22 - Feb 23
Fall Line Condo B7 1 Bedroom Home
Dining

Fall Line Condo E1 1 Bedroom Condo

Fall Line Condo E1 1 Bedroom Condo
3.5 star property
Killington
Fall Line Condo E1 1 Bedroom Condo
Sauna

Sunrise Bear Ridge C4 4 Bedroom Condo

Sunrise Bear Ridge C4 4 Bedroom Condo
3.0 star property
Killington
Sunrise Bear Ridge C4 4 Bedroom Condo
Private kitchen

Pico Mountain Condo F106 3 Bedroom Home

Pico Mountain Condo F106 3 Bedroom Home
3.0 star property
Killington
The price is P33,794
P71,139 total
includes taxes & fees
Feb 16 - Feb 17
Pico Mountain Condo F106 3 Bedroom Home
Dining

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 P21,629
P47,009 total
includes taxes & fees
Feb 16 - Feb 17
Mountain Green Resort by Killington VR - 1 Bedrooms
Living area

Whitetail Chalet 4 Bedroom Home

Whitetail Chalet 4 Bedroom Home
3.0 star property
Killington
The price is P45,226
P91,270 total
includes taxes & fees
Feb 18 - Feb 19
Whitetail Chalet 4 Bedroom Home
1 bedroom, free WiFi

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 P15,294
P30,024 total
includes taxes & fees
Feb 17 - Feb 18
Fall Line Condos by Killington VR - Studios
Living area

Shreadquarters 3 Bedroom Home

Shreadquarters 3 Bedroom Home
3.0 star property
Killington
Shreadquarters 3 Bedroom Home
View from property

Whiffletree I5 3 Bedroom Condo

Whiffletree I5 3 Bedroom Condo
3.0 star property
Killington
Whiffletree I5 3 Bedroom Condo
Exterior

Fall Line Condos by Killington VR - 3 Bedrooms

Fall Line Condos by Killington VR - 3 Bedrooms
3.5 star property
Killington
The price is P44,036
P89,593 total
includes taxes & fees
Feb 24 - Feb 25
Fall Line Condos by Killington VR - 3 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

Mountain Sports Inn

Mountain Sports Inn

10/10 Excellent
"Great room, great breakfast, great staff. Easy location to get to the slopes each morning well before start time. Thanks, Dave Oh, yes I will stay here each year and in fact I will be back in 10 days for another week"
David 5-night trip
Posted 1 day ago
Mountain Sports Inn

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! 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 vacation rental in Windsor?

Yes, we offer vacation rentals in Windsor close to Path of Life Garden, or you can select a more secluded option if you're looking for extra privacy while you relax. 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 vacation rentals are there in Windsor?

With 12 Expedia vacation rentals, you're sure 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 vacation rentals like in Windsor?

Vacation rentals are private properties you can stay in for several days or more in Windsor. Vacation rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for family gatherings.