Windsor Holiday 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
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Windsor holiday rentals

Living room

Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
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

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The Suites at Killington Center
Aerial view

Mountain Green

Mountain Green
2.0 star property
Killington
7.4 out of 10, Good, (21 reviews)
"Great !"
United States
Raul
The price is HK$1,369
HK$1,837 total
includes taxes & fees
11 Mar - 12 Mar
Mountain Green
Exterior

Fall Line Condos by Killington VR - 2 Bedrooms

Fall Line Condos by Killington VR - 2 Bedrooms
3.5 star property
Killington
The price is HK$1,890
HK$5,578 total
includes taxes & fees
12 Mar - 13 Mar
Fall Line Condos by Killington VR - 2 Bedrooms
Interior

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
Front of property

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is HK$8,610
HK$13,391 total
includes taxes & fees
12 Mar - 13 Mar
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
In-room dining

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 HK$1,439
HK$2,342 total
includes taxes & fees
15 Mar - 16 Mar
Brook Road Condo
Living area

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is HK$1,626
HK$6,123 total
includes taxes & fees
11 Mar - 12 Mar
Breakaway House by Killington Vacation Rentals
Private kitchen

Alpine Court Chalet 4 Bedroom Home

Alpine Court Chalet 4 Bedroom Home
3.0 star property
Killington
Alpine Court Chalet 4 Bedroom Home
Living area

Whitetail Chalet 4 Bedroom Home

Whitetail Chalet 4 Bedroom Home
3.0 star property
Killington
The price is HK$3,581
HK$8,760 total
includes taxes & fees
11 Mar - 12 Mar
Whitetail Chalet 4 Bedroom Home
Pool

Mountain Green Condo 2b4 2 Bedroom Condo

Mountain Green Condo 2b4 2 Bedroom Condo
3.5 star property
Killington
The price is HK$3,321
HK$7,448 total
includes taxes & fees
15 Mar - 16 Mar
Mountain Green Condo 2b4 2 Bedroom Condo
Living area

Blue Haven 3 Bedroom Home

Blue Haven 3 Bedroom Home
3.0 star property
Killington
The price is HK$3,388
HK$8,454 total
includes taxes & fees
22 Mar - 23 Mar
Blue Haven 3 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.
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

Turn of River Lodge

Turn of River Lodge

10/10 Excellent
"This was the perfect lodging for my ski trip to Killington/Pico/Sugarbush/Stratton! As a solo female traveler, it's important to me to feel safe, which I absolutely did! I stayed in the Queen with private bathroom and felt right at home. The door had a good lock (inside and outside) so I always felt safe leaving my stuff for the day and sleeping at night. Everyone was so friendly here too. The room and bathroom were clean and the bed very comfy! The breakfast was great in the morning and the common area was cozy and a great place to hang out and meet others. There's also a shared fridge and microwave. Sometimes I could hear folks in the hallway at night, but I just put my sound machine on and it didn't bother me at all. The owner was very kind and helpful! I had to have a package delivered with a new phone and she made sure I got my package. She also delivered a phone message to my room for me. Excellent customer service! The lodge is only a few minutes drive from Killington resort and there are plenty of great restaurants and shopping nearby. I look forward to staying here again, maybe even in the warmer months to do some hiking. Overall a wonderful stay!:)"
Abby 6-night trip
Posted 21 hours ago
Turn of River Lodge

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 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.

What are some of the best holiday rentals that Windsor has to offer?

Idyllic Lakefront House Suited Two Families: This holiday home rental outside Windsor is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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.