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
10.0 out of 10, Exceptional, (30)
"Very relaxing house, we all enjoyed the fireplaces and pellet stove and the well-equipped kitchen allowed us to cook beautiful meals. The property is gorgeous and neighbors are far away. This was the perfect place for a friends reunion/ski trip!"
United States
Roy S.
Beautiful home offering privacy on 7 acres with private pond
Brook Road Cabin
3.5 star property
7.8 out of 10, Good, (9)
"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
Brook Road Condo
3.0 star property
8.8 out of 10, Excellent, (3)
"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 AU$441
includes taxes & fees
5 Nov - 6 Nov
Brook Road Condo
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
2.0 star property
10.0 out of 10, Exceptional, (8)
"Very relaxing stay! Cabins are beautiful, location is private and Wendi was very helpful with our stay"
United States
Nicholas M.
The price is AU$484
includes taxes & fees
11 Nov - 12 Nov
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
2.0 star property
10.0 out of 10, Exceptional, (17)
"We greatly enjoyed a quick get away to this beautiful sun-filled house! The house was exceptionally clean and comfortable, very relaxing place to stay! "
United States
Jonathan G.
The price is AU$696
includes taxes & fees
30 Oct - 31 Oct
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Addie's Place: A Quiet and Quirky Private Guesthouse
10.0 out of 10, Exceptional, (3)
"Perfect size and location! "
United States
Lyn H.
The price is AU$341
includes taxes & fees
22 Oct - 23 Oct
Addie's Place: A Quiet and Quirky Private Guesthouse
Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, (23)
"The treehouse is super comfortable and spacious and the lodge was very cozy with everything you need! Breakfast was great too :)"
Canada
Victoria M.
The price is AU$291
includes taxes & fees
2 Nov - 3 Nov
Treehouse at Wise Pines- SoBo
Fall into Cozy at Bigfoot Chalet
2.0 star property
10.0 out of 10, Exceptional, (14)
"We only stayed on night while exploring the area, but it was so lovely! The more we looked, the more cute, and thoughtful elements we sae. Would definitely come back!"
United States
Thomas O.
The price is AU$738
includes taxes & fees
27 Oct - 28 Oct
Fall into Cozy at Bigfoot Chalet
Brook Road Cabin
9.8 out of 10, Exceptional, (17)
"Would go back!"
United States
Elizabeth C.
The price is AU$479
includes taxes & fees
3 Nov - 4 Nov
Brook Road Cabin
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.6 out of 10, Exceptional, (163)
"We very much enjoyed our stay, check in was a breeze and we found the cabin to be a cozy retreat. We have been looking for a place that had a bed and bath on first floor to accommodate some mobility limitations and this home was perfect having a single step on the front porch. We look forward to booking another trip with this host "
United States
Jennifer
The price is AU$567
includes taxes & fees
20 Oct - 21 Oct
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access
2.0 star property
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.
The price is AU$710
includes taxes & fees
20 Oct - 21 Oct
Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access
The Carol - 10 minutes to Okemo & Newly Renovated
10.0 out of 10, Exceptional, (6)
"Check in and check out were incredibly easy, house decor was eclectic upscale, beds were super comfortable. Thank you Chris! Would definitely stay here again"
United States
Esther K.
The price is AU$465
includes taxes & fees
26 Oct - 27 Oct
The Carol - 10 minutes to Okemo & Newly Renovated
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
10.0 out of 10, Exceptional, (16)
"Loved staying at this quaint cottage, the outside spaces were lovely and it was very clean! Communication with the owner was seamless and they were fantastic to deal with. I would highly recommend a stay here! "
United States
Lisa P.
The price is AU$707
includes taxes & fees
20 Oct - 21 Oct
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Cozy 2 BR Ski On Ski Off Condo in Killington's Sunrise Mountain Village. Pool. Hot Tub.
2.0 star property
9.4 out of 10, Exceptional, (3)
"Absolutely perfect spot. Kids and parents loved it. Everything you’re looking for in an on mountain condo. Pool and hot tub are a short drive away but we still used it. "
United States
nicholas d.
The price is AU$624
includes taxes & fees
20 Oct - 21 Oct
Cozy 2 BR Ski On Ski Off Condo in Killington's Sunrise Mountain Village. Pool. Hot Tub.
Luxury Condo Tucked in the Heart of Killington
8.0 out of 10, Very good, (1)
"The condo was in a beautiful location but was rather isolated from grocery and dining options. Our host was good at communicating however we received a message about the fireplace not being available to us a day before we came and we got there in the dark with no lights on. The condo itself could not really be called "luxury" as it was dated and lacked some basics like soap in the bathroom, a towel hook in the 1/2 bath, kleenex, cracked dishes, etc. Liked that it was near a waterfall and hiking...
United States
Dean
The price is AU$471
includes taxes & fees
20 Oct - 21 Oct
Luxury Condo Tucked in the Heart of Killington
Brook Road Condo
8.8 out of 10, Excellent, (14)
"Nice place close to the mountain!"
United States
Kevin N.
The price is AU$483
includes taxes & fees
17 Nov - 18 Nov
Brook Road Condo
MT Holly Ski/lake house hideaway(Avail. Daily, weekends & seasonally Dec-April)
9.8 out of 10, Exceptional, (20)
"Everything was as expected. Very clean, great location. Would stay again!"
United States
Jenna K.
The price is AU$835
includes taxes & fees
20 Oct - 21 Oct
MT Holly Ski/lake house hideaway(Avail. Daily, weekends & seasonally Dec-April)
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
10.0 out of 10, Exceptional, (11)
"My husband and i really enjoyed our stay at Jack S'bearo! Was a nice, cozy condo for a couple or a small family. Highly recommend!"
United States
Erin
The price is AU$424
includes taxes & fees
20 Oct - 21 Oct
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Wade's World- AC, Pool, Tennis, Bike to Mountain
2.0 star property
9.6 out of 10, Exceptional, (5)
"Perfectly described and so close the mountain. All you need!"
United States
Dana E.
The price is AU$526
includes taxes & fees
20 Oct - 21 Oct
Wade's World- AC, Pool, Tennis, Bike to Mountain
Killington condo 5 min to killington resort
9.4 out of 10, Exceptional, (8)
"We loved staying here. It was comfortable, had everything we needed. 100% would stay here again!"
United States
Vanessa O.
The price is AU$501
includes taxes & fees
21 Oct - 22 Oct
Killington condo 5 min to killington resort
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 favourite 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 depend 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 AU$291 per night. Entering your travel dates in the search wizard might find you 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 10 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.