Photo by Joel Holland

Windsor Holiday Rentals

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Holiday Rentals in Windsor

The Dylin by Mint House

4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (113)
"Great location and very comfortable stay. Love the extra space to hang out."
United States
Brian
The Dylin by Mint House

Charming 3-bedroom Duplex unit with WiFi in Cottage Grove

Village of Cottage Grove
10.0 out of 10, Exceptional, (7)
"Perfect place to stay to visit my daughter who lives in East Madison. Quiet neighborhood. Easy access to Madison and airport. House was equipped with what we needed--my daughter and me. Beds were VERY comfortable. We will be returning in October for another visit. Owner as so prompt to address any needs we had. "
United States
Janice A.
The price is NZ$830
includes taxes & fees
16 Nov - 17 Nov
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove

Pool with Slide. Great for Business Travelers!

Fitchburg
The price is NZ$306
includes taxes & fees
13 Nov - 14 Nov
Pool with Slide. Great for Business Travelers!

Hot Tub - King Suite - Game Room - Large Groups

Sun Prairie
10.0 out of 10, Exceptional, (13)
"We had a great visit "
United States
Jennifer D.
The price is NZ$1,203
includes taxes & fees
12 Nov - 13 Nov
Hot Tub - King Suite - Game Room - Large Groups

Private Pool - HOT TUB - Sauna - Game Room - Pets

Sun Prairie
10.0 out of 10, Exceptional, (6)
"The Sun Prairie house perfectly met the goals for our family gathering of six adults and golden retriever for social and private space and so many entertainment options! The house was spotless, the neighborhood quiet, with Woodmans close by for shopping. We had 5 days of sunshine, golfing nearby courses, enjoying afternoon pool time, evening hot tub, and bug-free outdoor dining-so private and relaxing! We never ran out of room for food/drinks in the large volume fridge (loved the beverage...
United States
Patricia M.
Private Pool - HOT TUB - Sauna - Game Room - Pets

Enjoy Nature with Full Comfort!

Verona
9.4 out of 10, Exceptional, (35)
"I enjoyed this location. Was the perfect size for one person (or a couple’s getaway). The room was secure and safe. Clean and had some nice little extras in the room. Marca was very attentive to all communication we had. The scenery out the big bay window was lovely as well. Would stay again if the opportunity arose."
United States
Jennifer B.
The price is NZ$227
includes taxes & fees
17 Nov - 18 Nov
Enjoy Nature with Full Comfort!

King Suite | Free Breakfast. Pool and Hot Tub

Middleton
8.6 out of 10, Excellent, (4)
"Back burner of stovetop nonfunctional."
United States
John H.
The price is NZ$262
includes taxes & fees
16 Nov - 17 Nov
King Suite | Free Breakfast. Pool and Hot Tub

King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

Fitchburg
The price is NZ$355
includes taxes & fees
13 Nov - 14 Nov
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

Sun Prairie
10.0 out of 10, Exceptional, (10)
"Perfect property for our group, will definitely be back.Immaculately maintained, excellent kitchen for preparing large group meals. Would recommend visitors bring spices, dried goods (flour, sugar, etc), storage containers/bags, wraps/foils and extra paper towels. If you forget there is excellent shopping and food options within 5 to 7 minute drive (costco, woodmans, aldi).Host was reaponsive leading up to our trip and extremely friendly and flexible. Even did a call with me to ensure we would...
United States
Nick he-him M.
The price is NZ$1,026
includes taxes & fees
11 Nov - 12 Nov
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

One Bedroom King with Office with views of Lake Monona in the heart of downtown.

2.0 star property
Downtown Madison
10.0 out of 10, Exceptional, (2)
"Our stay at The Saddlery was great. The check in process was easy and the communication was amazing. I had missed adding parking to our reservation and I was notified to confirm if parking was needed or not. The building and room was clean and up to date. The room was also nice and quiet for a great nights rest. Highly recommended. "
United States
NICOLE R.
The price is NZ$583
includes taxes & fees
11 Nov - 12 Nov
One Bedroom King with Office with views of Lake Monona in the heart of downtown.

1 Bedroom - 1220 Canterbury Ct

Sun Prairie
The price is NZ$508
includes taxes & fees
22 Nov - 23 Nov
1 Bedroom - 1220 Canterbury Ct

Doty ★ Walk to Everything -Hotel Quality- Downtown

Downtown Madison
9.8 out of 10, Exceptional, (35)
"Great location, family friendly. Would stay again!"
United States
Sarah S.
The price is NZ$2,276
includes taxes & fees
22 Nov - 23 Nov
Doty ★ Walk to Everything -Hotel Quality- Downtown

Capital PrimeTime - 6 Miles from Madison w/ fireplace

Sun Prairie
9.8 out of 10, Exceptional, (29)
"Would recommend - very good location, nice space, and great host!"
United States
James O.
The price is NZ$1,117
includes taxes & fees
11 Nov - 12 Nov
Capital PrimeTime - 6 Miles from Madison w/ fireplace

Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Merrimac
9.8 out of 10, Exceptional, (20)
"Great property, beautiful view, very unique design on this property. The property was well prepared for our visit. Just sits on the side of a hill with a view in the distance of the Wisconsin River. I highly recommend it."
United States
Jay T.
The price is NZ$703
includes taxes & fees
10 Dec - 11 Dec
Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Monona
9.8 out of 10, Exceptional, (47)
"We absolutely loved this place! Perfect spot with a pier on the water. My kids were catching fish within minutes. The house was perfect and Jake couldn’t have been easier to work with. Highly recommend! "
United States
Mark G.
The price is NZ$886
includes taxes & fees
17 Nov - 18 Nov
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Entire 3 Bedroom with Fireplace - sleeps 12

Sun Prairie
9.8 out of 10, Exceptional, (15)
"Great property, great location… with awesome dining and shopping options - a short drive to Madison without the congestion of being in Madison downtown. Tami was very helpful. Would definitely come back! Thanks Tami for a wonderful stay."
United States
Smitha S.
The price is NZ$1,075
includes taxes & fees
11 Nov - 12 Nov
Entire 3 Bedroom with Fireplace - sleeps 12

3BR/3BA Home | Dual Living Spaces

Fitchburg
10.0 out of 10, Exceptional, (16)
"Beautiful furnishings, very clean, Well stocked. Would definitely stay there again. The host was very responsive."
United States
Valerie S.
The price is NZ$1,415
includes taxes & fees
11 Nov - 12 Nov
3BR/3BA Home | Dual Living Spaces

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

2.0 star property
Middleton
The price is NZ$566
includes taxes & fees
11 Nov - 12 Nov
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

Free Breakfast. Pool & Hot Tub. Near UW-Madison!

2.0 star property
Madison
The price is NZ$501
includes taxes & fees
23 Nov - 24 Nov
Free Breakfast. Pool & Hot Tub. Near UW-Madison!

Studio Queen in the heart of downtown.

2.0 star property
Downtown Madison
The price is NZ$491
includes taxes & fees
11 Nov - 12 Nov
Studio Queen in the heart of downtown.
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$227 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 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?

Private Pool - HOT TUB - Sauna - Game Room - Pets: This holiday home rental outside of Windsor offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable 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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.