Windsor Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Windsor holiday rentals

Living room

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
Aerial view

Condo in Killington

The Suites at Killington Center
3.5 star property
The price is S$471
includes taxes & fees
3 Mar - 4 Mar
The Suites at Killington Center
Aerial view

Condo resort in Killington

Mountain Green
2.0 star property
7.2 out of 10, Good, (20 reviews)
"Great !"
United States
Raul
The price is S$317
includes taxes & fees
11 Mar - 12 Mar
Mountain Green
Exterior

Condo in Killington

Mountain Green Resort by Killington VR - 2 Bedrooms
2.0 star property
The price is S$1,021
includes taxes & fees
5 Mar - 6 Mar
Mountain Green Resort by Killington VR - 2 Bedrooms
Interior

Apartment in Killington

Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country
2.0 star property
The price is S$439
includes taxes & fees
3 Mar - 4 Mar
Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country
Interior

Cottage in Ludlow

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
The price is S$2,164
includes taxes & fees
12 Mar - 13 Mar
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
In-room dining

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$378
includes taxes & fees
9 Mar - 10 Mar
Brook Road Condo
Living area

Holiday Home in Killington

Breakaway House by Killington Vacation Rentals
3.0 star property
The price is S$1,011
includes taxes & fees
1 Mar - 2 Mar
Breakaway House by Killington Vacation Rentals
Interior

Condo in Killington

Mountain Green Condo 3a2 1 Bedroom Condo
3.5 star property
The price is S$794
includes taxes & fees
17 Mar - 18 Mar
Mountain Green Condo 3a2 1 Bedroom Condo
Private kitchen

Holiday Home in Killington

Pico Mountain Condo F106 3 Bedroom Home
3.0 star property
Pico Mountain Condo F106 3 Bedroom Home
Interior

Apartment in Killington

Killington Center 531
3.5 star property
The price is S$440
includes taxes & fees
3 Mar - 4 Mar
Killington Center 531
Pool

Condo in Killington

Mountain Green Condo 1a8 1 Bedroom Condo
3.5 star property
The price is S$905
includes taxes & fees
4 Mar - 5 Mar
Mountain Green Condo 1a8 1 Bedroom Condo
Sauna

Condo in Killington

Sunrise Bear Ridge C4 4 Bedroom Condo
3.0 star property
The price is S$1,749
includes taxes & fees
5 Mar - 6 Mar
Sunrise Bear Ridge C4 4 Bedroom Condo
Living area

Holiday Home in Killington

Blue Haven 3 Bedroom Home
3.0 star property
The price is S$1,417
includes taxes & fees
22 Mar - 23 Mar
Blue Haven 3 Bedroom Home
Living area

Holiday Home in Killington

Whitetail Chalet 4 Bedroom Home
3.0 star property
The price is S$1,715
includes taxes & fees
11 Mar - 12 Mar
Whitetail Chalet 4 Bedroom Home
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

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent
"Clean room, staff were super friendly and made sure me and my dog were comfortable. Love how dog friendly it was. Will definitely return!"
Paola 3-night trip
Posted 4 hours ago
Killington Mountain Lodge, Tapestry Collection by Hilton

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Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals in Windsor close to Path of Life Garden, 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 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.