Windsor Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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, (15 reviews)
"This property was extremely beautiful and peaceful. Loved being able to walk around the farm and say hi to the animals. The views of the mountains from the cabin or gorgeous, we enjoyed having our coffee on the porch each morning. Having fresh eggs and scones in our cabin upon arrival was a very nice surprise. Will definitely be staying there again."
United States
Brenda
The price is ￥17,790
￥28,003 total
includes taxes & fees
Nov 17 - Nov 18
Fat Sheep Farm & Cabins
A spacious living room with a high ceiling, wooden beams, a fireplace, and large windows.

2. Game Room, Fire Pit & Views! Spacious Ludlow Home

Game Room, Fire Pit & Views! Spacious Ludlow Home
3.0 star property
Ludlow
The price is ￥45,981
￥124,997 total
includes taxes & fees
Nov 12 - Nov 13
Game Room, Fire Pit & Views! Spacious Ludlow Home
A red brick building with a classical facade, a covered walkway, and a well-maintained lawn.

3. 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 ￥29,074
￥47,318 total
includes taxes & fees
Nov 12 - Nov 13
Brook Road Condo
Aerial view

4. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is ￥27,375
￥64,873 total
includes taxes & fees
Nov 12 - Nov 13
The Suites at Killington Center
A modern living room with a sectional sofa, a wooden coffee table, and a large window with blinds.

5. 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 ￥27,117
￥45,195 total
includes taxes & fees
Nov 11 - Nov 12
Brook Road Cabin
A spacious living area with a fireplace, a dining area, and a kitchen.

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

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is ￥217,106
￥339,813 total
includes taxes & fees
Nov 17 - Nov 18
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
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.
View all properties

Find vacation rentals that suit your style

apart-hotel image
Aparthotels
Aparthotels
Apartment image
Apartments
Apartments

Top Windsor Hotel Reviews

A multi-story building with a central staircase, outdoor seating, and a sunset sky.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville

10/10 Excellent

When I walked in the door I was dumbfounded with the size of the room, it was huge to call it a room does not do it justice. 2 stories, full living and dining room, you have to call it a villa, or a house I'd live in! Clean comfortable, roomy, held 6 adults easily! Very new very modern, looked and smelled freshly renovated! Much more than I was expecting !
United States
Jamie
Reviewed September 26, 2015
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

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.