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

Search Holiday Rentals in Windsor

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

Our top choices for Windsor holiday 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, (16 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 2.874.310 ₫
4.524.329 ₫ total
includes taxes & fees
18 Nov - 19 Nov
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 7.428.939 ₫
20.195.226 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Game Room, Fire Pit & Views! Spacious Ludlow Home
A cozy living room with a sofa, a dining table with chairs, a small side table, and a wooden floor.

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 4.697.336 ₫
7.644.914 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Brook Road Condo
Aerial view

4. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is 5.801.465 ₫
11.997.992 ₫ total
includes taxes & fees
22 Nov - 23 Nov
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 4.393.240 ₫
7.322.058 ₫ total
includes taxes & fees
12 Nov - 13 Nov
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 35.076.846 ₫
54.902.157 ₫ total
includes taxes & fees
22 Nov - 23 Nov
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

On The River Inn

On The River Inn

8/10 Good
"My only quibble was that the bar and restaurant were not open during our 2 night stay and only on weekends. The hotel amenities were superb, the overall upkeep of this property and the decor with props etc was exceptional...."
Gail 2-night trip
Posted 6 hours ago
On The River Inn

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals in Windsor close to Maze of Adventure, 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 11 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 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 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.