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Windsor Holiday Rentals

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Holiday Rentals in Windsor

Aparthotel in Tenney-Lapham

4.0 star property
9.4 out of 10, Exceptional, (116)
"Great location and very comfortable stay. Love the extra space to hang out."
United States
Brian
The price is AU$189
includes taxes & fees
29 Dec - 30 Dec
The Dylin by Mint House

Cottage in Poynette

3.0 star property
10.0 out of 10, Exceptional, (1)
"The cabins looked small from the outside, but we're actually very spacious we didn't feel cramped everything was very clean there was a full kitchen a table big enough to sit at least four. I think the only thing that wasn't 100% perfect was the beds are a little small they were stiff and the pillows were also very small and serviceable. I would still definitely stay there again 100% and would recommend it to everyone!"
United States
Shelley
Lake Wisconsin Resort

Holiday Home in Sun Prairie

10.0 out of 10, Exceptional, (259)
"A great stay! A wonderful location and excellent property, along with kind and warm hosts. Thank you. "
United States
Rachel Z.
A Pleasant Retreat- No Cleaning Fee & New Discounts

Condo in Sun Prairie

9.8 out of 10, Exceptional, (31)
"Everything about our experience staying here was excellent! Communication, very clean, nicely decorated, and in a great neighborhood with amenities close by."
United States
Nancy R.
The price is AU$968
includes taxes & fees
12 Dec - 13 Dec
Capital PrimeTime - 6 Miles from Madison w/ fireplace

Cottage in Poynette

9.8 out of 10, Exceptional, (252)
"This was a nice place to stay that was away from hustle of the city. It was beautiful outside and the cabin was cute and cozy."
United States
Pauley A.
Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!

Cottage in Poynette

9.8 out of 10, Exceptional, (212)
"Wonderful cottage with everything we needed for a great stay. Loved watching the hummingbirds."
United States
Scott B.
Island View Hideaway-Peaceful, On Water, Canoe, Scenic, Birds, Nature, Sandbars!

Holiday Home in Spring Harbor

10.0 out of 10, Exceptional, (131)
"It was great!"
United States
Guitar string S.
Conveniently Located just off University Avenue on Madison's West Side

Holiday Home in Sun Prairie

10.0 out of 10, Exceptional, (6)
"The house is great and the facilities in the house were well-functioning, and the dish washer saved us much time. The neighborhood is quiet and great views. We enjoyed our stay."
United States
Patti M.
The price is AU$1,196
includes taxes & fees
2 Dec - 3 Dec
Private Pool - HOT TUB - Sauna - Game Room - Pets

Holiday Home in Downtown Madison

9.8 out of 10, Exceptional, (36)
"Beautiful apartment with all we needed for a comfortable family July 4th weekend away!! "
United States
Mindi Z.
The price is AU$449
includes taxes & fees
9 Dec - 10 Dec
Doty ★ Walk to Everything -Hotel Quality- Downtown

Holiday Home in Madison

10.0 out of 10, Exceptional, (146)
"Came to Madison for a family wedding. Had a great time staying in the house, really enjoying the screened porch, everything was perfect for our needs."
United States
Lesley A D.
ONE OF A KIND vacation rental with a view

Holiday Home in Faircrest

10.0 out of 10, Exceptional, (119)
"Scenic property, super zen, lovely hosts!"
United States
Christina C.
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

Apartment in Fitchburg

The price is AU$211
includes taxes & fees
7 Dec - 8 Dec
Pool with Slide. Great for Business Travelers!

Cabin in Merrimac

9.8 out of 10, Exceptional, (21)
"Enjoyed a wonderful stay."
United States
Michael D.
The price is AU$580
includes taxes & fees
2 Dec - 3 Dec
Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Condo in Madison

10.0 out of 10, Exceptional, (1)
"It was comfortable and clean and the staff was so nice. It was well located and the pool and hot tub were lovely as well."
United States
Joy E.
The price is AU$396
includes taxes & fees
30 Nov - 1 Dec
Free Breakfast Pool & Hot Tub. Near UW-Madison

Cottage in McFarland

10.0 out of 10, Exceptional, (201)
"What a lovely place to spend a few days with family! There was so much to do within a short distance but we loved being able to just chill on the water. We had a wonderful stay and can’t wait to visit again. Would highly recommend! "
United States
Jody G.
Madison & ~UW~-Madison Area Lakefront Home

Holiday Home in Monona

10.0 out of 10, Exceptional, (51)
"Great stay - very relaxing!"
United States
Karen S.
On the Yahara River, access to Madison Lakes

Holiday Home in Monona

9.8 out of 10, Exceptional, (47)
"Such a nice house! Great location and excellent amenities!"
United States
Carson M.
The price is AU$768
includes taxes & fees
9 Dec - 10 Dec
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Holiday Home in Merrimac

8.2 out of 10, Very good, (23)
"Plenty of sleeping options for kids.Close to Devils Head.Many restaurants within a short drive."
United States
Wesley R.
Historic Home Near Wi Dells, Lake Wi & Party Space Avail!

Condo in Deerfield

10.0 out of 10, Exceptional, (133)
"Clean, quiet neighborhood, and plenty of space for our whole crew during Ironman weekend. Would recommend for anyone visiting the Madison area. "
United States
Alex T.
Exceptional 4 Bed 3 Bath Hot tub next to woods -Comfortable! - 21 min to Madison

Holiday Home in McFarland

10.0 out of 10, Exceptional, (12)
"Nice stay"
United States
Rebecca S.
Charming 4 Bed, 2.5 Bath home minutes from Madison perfect for any occasion.
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$189 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 Mousehouse Cheesehaus, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Windsor has a good selection of restaurants. Make sure you have time to check out the shopping and sporting events during your trip.

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

A Pleasant Retreat- No Cleaning Fee & New Discounts: This holiday home rental outside of Windsor offers a patio, a garden and a BBQ to help you feel perfectly comfortable 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 and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Windsor?

Explore the area and family-friendly sights such as Mousehouse Cheesehaus, or get out into nature at a spot like Olbrich Botanical Gardens. In the wider area, you’ll find East Towne Mall and Madison Area Technical College.

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 extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a family getaway.