Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

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

Okemo Westwood Condo 3 Bedroom Condo by RedAwning

Okemo Westwood Condo 3 Bedroom Condo by RedAwning
3.5 star property
Ludlow
The price is NZ$2,603
includes taxes & fees
12 Feb - 13 Feb
Okemo Westwood Condo 3 Bedroom Condo by RedAwning

Mountain Green

Mountain Green
2.0 star property
Killington
7.0 out of 10, Good, (19 reviews)
"Great !"
United States
Raul
The price is NZ$449
includes taxes & fees
11 Mar - 12 Mar
Mountain Green

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
The price is NZ$799
includes taxes & fees
18 Feb - 19 Feb
Hotel Style Condo Promising a Comfortable and Convenient Retreat Right in the Heart of Vermont ski Country

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is NZ$821
includes taxes & fees
18 Feb - 19 Feb
The Suites at Killington Center

Mountain Green Resort

Mountain Green Resort
4.0 star property
Killington
4.0 out of 10, (2 reviews)
"Clean room, elevator broken and not enough bathroom towels."
United States
Jing
Mountain Green Resort

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 NZ$496
includes taxes & fees
22 Feb - 23 Feb
Brook Road Condo

Fall Line Condos by Killington VR - 2 Bedrooms

Fall Line Condos by Killington VR - 2 Bedrooms
3.5 star property
Killington
The price is NZ$1,589
includes taxes & fees
26 Feb - 27 Feb
Fall Line Condos by Killington VR - 2 Bedrooms

Mountain Green 3G6

Mountain Green 3G6
3.0 star property
Killington
Mountain Green 3G6

Mountain Green Resort by Killington VR - 1 Bedrooms

Mountain Green Resort by Killington VR - 1 Bedrooms
3.5 star property
Killington
8.0 out of 10, Very good, (1 review)
"I had trouble getting in and out of the inner roads around the buildings and had to wait to use my rental car until the bus traffic cleared Old Mill Rd. to slush. This made me kind of locked in, but the bus service to and from the ski lodges did make it possible to ski. And that was the main reason I stayed at Mountain Green Resort the proximity and shuttle service."
United States
Scott
The price is NZ$1,487
includes taxes & fees
16 Feb - 17 Feb
Mountain Green Resort by Killington VR - 1 Bedrooms

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is NZ$1,401
includes taxes & fees
12 Feb - 13 Feb
Breakaway House by Killington Vacation Rentals

Fall Line Condo B7 1 Bedroom Home

Fall Line Condo B7 1 Bedroom Home
3.5 star property
Killington
The price is NZ$1,270
includes taxes & fees
22 Feb - 23 Feb
Fall Line Condo B7 1 Bedroom Home

Fall Line Condos by Killington VR - 1 Bedrooms

Fall Line Condos by Killington VR - 1 Bedrooms
3.5 star property
Killington
Fall Line Condos by Killington VR - 1 Bedrooms

Fall Line Condo E1 1 Bedroom Condo

Fall Line Condo E1 1 Bedroom Condo
3.5 star property
Killington
The price is NZ$1,616
includes taxes & fees
18 Feb - 19 Feb
Fall Line Condo E1 1 Bedroom Condo

Fall Line Condos by Killington VR - Studios

Fall Line Condos by Killington VR - Studios
2.0 star property
Killington
7.0 out of 10, Good, (2 reviews)
"Yes by a shuttle very easy"
United States
Philip
The price is NZ$640
includes taxes & fees
12 Feb - 13 Feb
Fall Line Condos by Killington VR - Studios

Sunrise Bear Ridge C4 4 Bedroom Condo

Sunrise Bear Ridge C4 4 Bedroom Condo
3.0 star property
Killington
The price is NZ$2,275
includes taxes & fees
25 Feb - 26 Feb
Sunrise Bear Ridge C4 4 Bedroom Condo

Shreadquarters 3 Bedroom Home

Shreadquarters 3 Bedroom Home
3.0 star property
Killington
The price is NZ$2,256
includes taxes & fees
23 Feb - 24 Feb
Shreadquarters 3 Bedroom Home

The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home

The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home
3.0 star property
Killington
The price is NZ$2,967
includes taxes & fees
17 Feb - 18 Feb
The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home

Whiffletree I5 3 Bedroom Condo

Whiffletree I5 3 Bedroom Condo
3.0 star property
Killington
Whiffletree I5 3 Bedroom Condo

Mountain Green Resort by Killington VR - 2 Bedrooms

Mountain Green Resort by Killington VR - 2 Bedrooms
2.0 star property
Killington
The price is NZ$1,372
includes taxes & fees
5 Mar - 6 Mar
Mountain Green Resort by Killington VR - 2 Bedrooms
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

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as NZ$311 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

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

Idyllic Lakefront House Suited Two Families: This holiday home rental outside of 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 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.