Holiday Rentals in Windsor

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Holiday Rentals in Windsor

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 €180
includes taxes & fees
1 Dec - 2 Dec
Addie's Place: A Quiet and Quirky Private Guesthouse

Treehouse at Wise Pines- NoBo

Woodstock
9.8 out of 10, Exceptional, (13)
"Unique settings. Loved the accommodations "
United States
Gabriela
The price is €165
includes taxes & fees
2 Dec - 3 Dec
Treehouse at Wise Pines- NoBo

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

2.0 star property
Sunapee
10.0 out of 10, Exceptional, (18)
"Great home. The hosts were accessible and responded quickly to questions. Definitely will stay there again!"
United States
Ellen V.
The price is €386
includes taxes & fees
2 Dec - 3 Dec
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

Brook Road Condo

3.0 star property
Goshen
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 €248
includes taxes & fees
30 Nov - 1 Dec
Brook Road Condo

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Sharon
10.0 out of 10, Exceptional, (3)
"Very welcoming, awesome weekend getaway."
United States
Zachary B.
The price is €230
includes taxes & fees
3 Dec - 4 Dec
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Ben & Jerry Suite | Skiing | Hiking | Biking

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 €172
includes taxes & fees
1 Dec - 2 Dec
Ben & Jerry Suite | Skiing | Hiking | Biking

The Suites at Killington Center

3.5 star property
Killington
The price is €294
includes taxes & fees
1 Dec - 2 Dec
The Suites at Killington Center

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

2.0 star property
Cavendish
10.0 out of 10, Exceptional, (10)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is €313
includes taxes & fees
8 Dec - 9 Dec
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

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

Clock Tower Base Area
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is €224
includes taxes & fees
1 Dec - 2 Dec
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

2.0 star property
Plymouth
10.0 out of 10, Exceptional, (14)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
United States
Ed N.
The price is €422
includes taxes & fees
4 Dec - 5 Dec
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Killington Blue Studio: Sleeps 4, Close to Mtn 123

Killington
9.4 out of 10, Exceptional, (9)
"Great location and clean property"
United States
KEVIN C.
The price is €201
includes taxes & fees
1 Dec - 2 Dec
Killington Blue Studio: Sleeps 4, Close to Mtn 123

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

Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

Newbury
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 €398
includes taxes & fees
30 Nov - 1 Dec
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

Brook Road Cabin

3.5 star property
Goshen
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

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 €208
includes taxes & fees
1 Dec - 2 Dec
Fall Line Small Studio - Perfect for Two - On Shuttle Route w/ Amenities B4A

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton
9.6 out of 10, Exceptional, (166)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
The price is €323
includes taxes & fees
15 Dec - 16 Dec
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

2.0 star property
Killington
10.0 out of 10, Exceptional, (11)
"The cabin was cozy. It was set up nicely and had all the necessities we needed."
United States
Philip
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

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

Killington
9.4 out of 10, Exceptional, (9)
"Great property, as advertised."
United States
Chris A.
The price is €234
includes taxes & fees
30 Nov - 1 Dec
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

Efficient condo near slopes with kitchenette & great location

Ludlow
8.6 out of 10, Excellent, (32)
"great location, close walkto store, restaurants. Okemoabout a minute drive toparking lots. "
United States
C A.
The price is €201
includes taxes & fees
1 Dec - 2 Dec
Efficient condo near slopes with kitchenette & great location

Brook Road Cabin

Goshen
9.8 out of 10, Exceptional, (17)
"Would go back!"
United States
Elizabeth C.
The price is €267
includes taxes & fees
30 Nov - 1 Dec
Brook Road Cabin
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, apart-hotels, 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 €224 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?

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable: This holiday home rental outside of Windsor is located in the city centre, and has a fireplace, a patio and laundry facilities to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

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.