Photo by mike dobias

Windsor Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Tonight
10 Jan - 11 Jan
Tomorrow
11 Jan - 12 Jan
Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan

Our top choices for Windsor holiday rentals

In-room dining
Brook Road Condo

Holiday Home in Goshen

Brook Road Condo
3.0 star property
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 S$386
includes taxes & fees
11 Jan - 12 Jan
Brook Road Condo
Aerial view
Mountain Green

Condo resort in Killington

Mountain Green
2.0 star property
6.8 out of 10, (17 reviews)
"Great communication from Jeff."
United States
Dennis
The price is S$359
includes taxes & fees
13 Jan - 14 Jan
Mountain Green
Exterior
Fall Line Condos by Killington VR - 2 Bedrooms

Condo in Killington

Fall Line Condos by Killington VR - 2 Bedrooms
3.5 star property
The price is S$889
includes taxes & fees
12 Jan - 13 Jan
Fall Line Condos by Killington VR - 2 Bedrooms
Living room
Brook Road Cabin

Cottage in Goshen

Brook Road Cabin
3.5 star property
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
Living area
The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home

Holiday Home in Killington

The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home
3.0 star property
The price is S$1,503
includes taxes & fees
12 Jan - 13 Jan
The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home
Exterior
Fall Line Small Studio - Perfect For Two - On Shuttle Route W/ Amenities G6a 1 Bedroom Condo

Condo in Killington

Fall Line Small Studio - Perfect For Two - On Shuttle Route W/ Amenities G6a 1 Bedroom Condo
2.0 star property
The price is S$466
includes taxes & fees
14 Jan - 15 Jan
Fall Line Small Studio - Perfect For Two - On Shuttle Route W/ Amenities G6a 1 Bedroom Condo
Exterior
Killington Ski Resort VT Vacation Condos

Condo in Killington

Killington Ski Resort VT Vacation Condos
3.5 star property
The price is S$406
includes taxes & fees
11 Jan - 12 Jan
Killington Ski Resort VT Vacation Condos
Living area
Breakaway House by Killington Vacation Rentals

Holiday Home in Killington

Breakaway House by Killington Vacation Rentals
3.0 star property
The price is S$1,038
includes taxes & fees
13 Jan - 14 Jan
Breakaway House by Killington Vacation Rentals
Pool
Mountain Green Condo 1c7 1 Bedroom Condo

Condo in Killington

Mountain Green Condo 1c7 1 Bedroom Condo
2.0 star property
The price is S$1,003
includes taxes & fees
22 Jan - 23 Jan
Mountain Green Condo 1c7 1 Bedroom Condo
Living area
Fall Line Condo B2 3 Bedroom Condo

Condo in Killington

Fall Line Condo B2 3 Bedroom Condo
2.0 star property
4.0 out of 10, (1 review)
"This property should not be rented and I body ever got back to us and toilet was broken. You shouldn’t market this on Expedia. "
Canada
Philip Ross
The price is S$1,619
includes taxes & fees
15 Jan - 16 Jan
Fall Line Condo B2 3 Bedroom Condo
Private kitchen
Alpine Court Chalet 4 Bedroom Home

Holiday Home in Killington

Alpine Court Chalet 4 Bedroom Home
3.0 star property
Alpine Court Chalet 4 Bedroom Home
Living area
Fall Line Condos by Killington VR - 3 Bedrooms

Condo in Killington

Fall Line Condos by Killington VR - 3 Bedrooms
3.5 star property
The price is S$1,209
includes taxes & fees
11 Jan - 12 Jan
Fall Line Condos by Killington VR - 3 Bedrooms
Exterior
Beautiful 2br/2ba Fall Line Condo W/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G6b 2 Bedroom Condo

Condo in Killington

Beautiful 2br/2ba Fall Line Condo W/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G6b 2 Bedroom Condo
3.5 star property
The price is S$972
includes taxes & fees
13 Jan - 14 Jan
Beautiful 2br/2ba Fall Line Condo W/ Mountain Views, Pool, Hot Tub, Sauna, Shuttle. G6b 2 Bedroom 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.
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

Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

10/10 Excellent
"Fun, innovative hotel perfect for families with kids. Conveniently located across from Sunapee mountain and next door to the Irish Pub. Can be a bit louder if you are next to the recreation room (closes at 10). "
Ryan 1-night trip
Posted 1 day ago
Hideaway Inn Mt.Sunapee

Explore a world of travel with Expedia

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.