Photo by William E Berry Jr.

Windsor Holiday Rentals

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Holiday Rentals in Windsor

Beautiful home offering privacy on 7 acres with private pond

West Windsor
10.0 out of 10, Exceptional, (30)
"Lots of space inside and out for my family to enjoy here! The sunny living room with its many windows brings the outside indoors."
United States
Eileen W.
The price is NZ$865
includes taxes & fees
12 Nov - 13 Nov
Beautiful home offering privacy on 7 acres with private pond

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Clock Tower Base Area
9.0 out of 10, Wonderful, (74)
"It was a perfect location and had everything we needed for a great stay."
United States
Danna K.
The price is NZ$451
includes taxes & fees
11 Nov - 12 Nov
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Killington
9.6 out of 10, Exceptional, (4)
"The place was clean and easy to get to. "
United States
Sarah Z.
The price is NZ$433
includes taxes & fees
11 Nov - 12 Nov
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Brook Road Cabin

3.5 star property
Goshen
7.8 out of 10, Good, (9)
"This little cabin is exactly what the owner purports it to be. No more; no less. It's quaint and the bedrooms are small. Because it's a cabin. The shower is small. Because it's a cabin. The TV and stove and sink are all small. Because it's a cabin! There are a few ants around, but there's Raid spray under the sink if you want to go that route. The occasional ant is going to show it's occasional self. It's a cabin. in the woods... I thought it was a fair accommodation for a fair price (just a...
United States
Jonathan
Brook Road Cabin

NEW Killington Studio: Great Location! Comfy. 431

Killington
8.8 out of 10, Excellent, (5)
"Great place to stay!"
United States
Carla M.
The price is NZ$404
includes taxes & fees
11 Nov - 12 Nov
NEW Killington Studio: Great Location! Comfy. 431

Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A

Killington
9.2 out of 10, Wonderful, (5)
"I don’t think I’ve ever had such wonderful service checking in and caring for our needs. Amazing response time and outstanding stay. Thank you."
United States
Margaret L.
The price is NZ$416
includes taxes & fees
11 Nov - 12 Nov
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A

Efficient condo near slopes with kitchenette & great location

Ludlow
8.6 out of 10, Excellent, (32)
"Stay was good. Couldn’t figure out the TV - Not sure if there was actually cable or not. Close to the main road so traffic was a bit loud. Other than that great stay. "
United States
Michael
The price is NZ$353
includes taxes & fees
17 Nov - 18 Nov
Efficient condo near slopes with kitchenette & great location

CozyDen-Location, Fireplace, Ski Off/Shuttle On!

Killington
10.0 out of 10, Exceptional, (1)
"Very quiet and private feeling even though it is in a condo like setting. Very clean, and had all the conveniences we needed (A/C, coffee maker, full kitchen appliances). And so kind and personal to leave some souvenirs of the area. We felt very comfortable when every we finished our day of sightseeing to come back to our home away from home. "
United States
denise k.
The price is NZ$497
includes taxes & fees
11 Nov - 12 Nov
CozyDen-Location, Fireplace, Ski Off/Shuttle On!

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Clock Tower Base Area
9.2 out of 10, Wonderful, (25)
"My sister and our two sons stayed here. It was simple, and extraordinarily convenient . It could use some updating - namely the pull out sofa mattress - labeled from 1992. Not comfortable. Besides that, it was right for the price if convenience is a priority."
United States
Justin B.
The price is NZ$410
includes taxes & fees
12 Nov - 13 Nov
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Jack S`Bearo - Slopes, Fireplace, Pool.

Killington
10.0 out of 10, Exceptional, (11)
"Nice space for 2 people - condo is well outfitted and incredibly convenient for Pico skiing. Nightlife in Killing still very convenient. Overall a very positive experience. "
United States
Jen R.
Jack S`Bearo - Slopes, Fireplace, Pool.

Alpine Oasis Studio at Mountain Green Resort Killington: Shuttle, Pool, Hot Tub, Gym, Deals!

Killington
9.6 out of 10, Exceptional, (5)
"The location was perfect. The unit had everything in it that we needed. We will definitely come back again!"
United States
AMY W.
Alpine Oasis Studio at Mountain Green Resort Killington: Shuttle, Pool, Hot Tub, Gym, Deals!

Let it Snow-Perfect Getaway! Cozy, Modern & convenience to everything!

Ludlow
9.8 out of 10, Exceptional, (74)
"This was a perfect spot for two to stay. Close walk to town and quick drive to Okemo. Had everything you would need to cook simple meals also."
United States
Dominique P.
The price is NZ$418
includes taxes & fees
12 Nov - 13 Nov
Let it Snow-Perfect Getaway! Cozy, Modern & convenience to everything!

Ben & Jerry Suite | Minutes to Woodstock | Hiking

Bridgewater
9.2 out of 10, Wonderful, (7)
"Close to Woodstock and market. Easy check in. Very quiet. Kurig, no cups for coffee."
United States
Nancy
The price is NZ$331
includes taxes & fees
16 Nov - 17 Nov
Ben & Jerry Suite | Minutes to Woodstock | Hiking

CozyCub- Location, Fireplace, Ski Off/Shuttle On!

Killington
10.0 out of 10, Exceptional, (22)
"Great place to stay and close to the mountain!"
United States
Sam S.
The price is NZ$496
includes taxes & fees
11 Nov - 12 Nov
CozyCub- Location, Fireplace, Ski Off/Shuttle On!

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

Killington
9.4 out of 10, Exceptional, (9)
"Could use some updates and the cleaning staff needs to be more thorough."
United States
Sarah S.
The price is NZ$471
includes taxes & fees
11 Nov - 12 Nov
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

2nd-floor downtown Ludlow studio condo with kitchenette, streaming

Ludlow
8.6 out of 10, Excellent, (4)
"Clean room. Glad that the text responses are quick. We weren't initially provided a room number and then the door code we were given would not work. Host responded and was able to reset code from afar. "
United States
Ana Maria C.
The price is NZ$417
includes taxes & fees
12 Nov - 13 Nov
2nd-floor downtown Ludlow studio condo with kitchenette, streaming

Cozy condo on ski shuttle route with free WiFi & full ktichen

Killington
8.4 out of 10, Very good, (38)
"Easy access to Killington Mountain "
United States
Dave S.
The price is NZ$497
includes taxes & fees
11 Nov - 12 Nov
Cozy condo on ski shuttle route with free WiFi & full ktichen

Killington 2 Story - Escape 2BR/2BA, Sleeps 6, Family & Friends Retreat w/ WiFi

2.0 star property
Killington
The price is NZ$549
includes taxes & fees
11 Nov - 12 Nov
Killington 2 Story - Escape 2BR/2BA, Sleeps 6, Family & Friends Retreat w/ WiFi

Addie's Place: A Quiet and Quirky Private Guesthouse

Hartford
10.0 out of 10, Exceptional, (4)
"Perfect size and location! "
United States
Lyn H.
The price is NZ$334
includes taxes & fees
11 Nov - 12 Nov
Addie's Place: A Quiet and Quirky Private Guesthouse

Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access

2.0 star property
The Woods
10.0 out of 10, Exceptional, (3)
"We headed up to Killington for some fun spring skiing with the fam and the place was great - spacious, well appointed, and comfortable. Would definitely stay again."
United States
Ryan T.
Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access
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$333 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 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.

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

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This holiday home rental outside of Windsor is located on a lake, and has a fireplace, a balcony 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 Path of Life Garden 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 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.