A snow-covered river valley with a bridge and a town.

Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Windsor vacation rentals

A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

1. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views! "
United States
Jessica
The price is ￥33,054
￥44,681 total
includes taxes & fees
Oct 26 - Oct 27
Fat Sheep Farm & Cabins
A modern living room with a sectional sofa, a wooden coffee table, and a large window with blinds.

2. Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
7.4 out of 10, Good, (10 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 ￥29,146
￥47,470 total
includes taxes & fees
Oct 4 - Oct 5
Brook Road Cabin
An aerial view of a residential area with houses, a swimming pool, and a mountain backdrop.

3. Killington Center 531

Killington Center 531
3.5 star property
Killington
Killington Center 531
A spacious living area with a fireplace, a dining area, and a kitchen.

4. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is ￥217,463
￥340,372 total
includes taxes & fees
Sep 26 - Sep 27
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

5. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is ￥24,765
￥62,168 total
includes taxes & fees
Oct 12 - Oct 13
The Suites at Killington Center
A snow-covered residential area with multi-story buildings, a ski slope in the background, and a clear sky.

6. Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (29 reviews)
"I enjoy the location "
United States
troy
Mountain Green

7. 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
A cozy living room with a sofa, a dining table with chairs, a small side table, and a wooden floor.

8. 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 ￥29,210
￥47,539 total
includes taxes & fees
Oct 19 - Oct 20
Brook Road Condo
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
"The property is beautiful and it’s convenient to the golf course. The rooms small but clean. Not a lot of privacy in the bathroom due to sliding door. Also, no coffee machines in the room"
Mary 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! 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 Maze of Adventure, 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.

What's the top vacation rental that Windsor has to offer?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: You might want to consider this vacation home rental near Windsor, which is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Windsor?

With 11 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.