Photo by Joel Holland

Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

The Dylin

The Dylin
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (123 reviews)
"Great stay at the Dylin"
United States
Lauri
The price is AU$200
includes taxes & fees
11 Feb - 12 Feb
The Dylin

Hot Tub - Game Room - 20 min to Capitol - Pets

Hot Tub - Game Room - 20 min to Capitol - Pets
2.0 star property
Sun Prairie
10.0 out of 10, Exceptional, (1 review)
"I had an excellent stay with Kingdom Hospitality. The home was immaculate, and I enjoyed the updated kitchen. The hot tub was clean, and a great amenity for stress relief. "
United States
Trey B.
The price is AU$972
includes taxes & fees
9 Feb - 10 Feb
Hot Tub - Game Room - 20 min to Capitol - Pets

Enjoy Nature with Full Comfort!

Enjoy Nature with Full Comfort!
Verona
9.2 out of 10, Wonderful, (39 reviews)
"Clean very friendly nice spot"
Canada
Oliver H.
The price is AU$193
includes taxes & fees
25 Jan - 26 Jan
Enjoy Nature with Full Comfort!

Cannery Square Short Term Rentals -104 by Patriot

Cannery Square Short Term Rentals -104 by Patriot
Sun Prairie
9.8 out of 10, Exceptional, (46 reviews)
"Roomy. Kitchen had basics. Good beds and pillows. "
United States
Susan
The price is AU$474
includes taxes & fees
25 Jan - 26 Jan
Cannery Square Short Term Rentals -104 by Patriot

Charming 3-bedroom Duplex unit with WiFi in Cottage Grove

Charming 3-bedroom Duplex unit with WiFi in Cottage Grove
Village of Cottage Grove
10.0 out of 10, Exceptional, (8 reviews)
"Stayed with friends for the weekend and really enjoyed the home. It was comfortable and had great amenities for our group!"
United States
Anakin F.
The price is AU$669
includes taxes & fees
19 Jan - 20 Jan
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove

2 Bedroom - Main Street Sun Prairie WI

2 Bedroom - Main Street Sun Prairie WI
Sun Prairie
9.6 out of 10, Exceptional, (38 reviews)
"Clean and quiet. Nice neighborhood amenities. "
United States
Mark L.
The price is AU$599
includes taxes & fees
25 Jan - 26 Jan
2 Bedroom - Main Street Sun Prairie WI

Hot Tub - Private Pool - Game Room - 20 min DT

Hot Tub - Private Pool - Game Room - 20 min DT
2.0 star property
Sun Prairie
10.0 out of 10, Exceptional, (2 reviews)
"The house was clean, large, and nicely decorated. It felt welcoming and homey. The host was friendly and responsive to our questions. "
United States
Ellen M.
Hot Tub - Private Pool - Game Room - 20 min DT

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is AU$206
includes taxes & fees
30 Jan - 31 Jan
Pool with Slide. Great for Business Travelers!

Cannery Square Short Term Rentals -102 by Patriot

Cannery Square Short Term Rentals -102 by Patriot
Sun Prairie
8.0 out of 10, Very good, (12 reviews)
"Was cute neighborhood and everything was very clean and close by"
United States
Bri
The price is AU$404
includes taxes & fees
1 Feb - 2 Feb
Cannery Square Short Term Rentals -102 by Patriot

King Suite | Free Breakfast. Pool and Hot Tub

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.0 out of 10, Very good, (5 reviews)
"Great place for a stay."
United States
Andy D.
The price is AU$215
includes taxes & fees
15 Jan - 16 Jan
King Suite | Free Breakfast. Pool and Hot Tub

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

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
2.0 star property
Middleton
10.0 out of 10, Exceptional, (2 reviews)
"We had a fantastic stay at this property, and it truly exceeded our expectations. The location is excellent—perfectly situated with convenient access to both the east and west sides of Madison, making it easy to get wherever we needed to go. The owners were incredibly helpful and responsive, answering the few questions we had quickly and kindly, which made the entire experience even smoother.One of the biggest highlights for us was the private fenced-in area, which was absolutely perfect for our...
United States
Jessi P.
The price is AU$449
includes taxes & fees
25 Jan - 26 Jan
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

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

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Monona
9.8 out of 10, Exceptional, (47 reviews)
"Clean and close to everything."
United States
Anonymous traveller
The price is AU$737
includes taxes & fees
22 Jan - 23 Jan
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

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

King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
Fitchburg
The price is AU$236
includes taxes & fees
30 Jan - 31 Jan
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

Studio Queen in the heart of downtown.

Studio Queen in the heart of downtown.
2.0 star property
Downtown Madison
10.0 out of 10, Exceptional, (1 review)
"Convenient location for events on the Capital Square, State Street and UW-Madison Campus."
United States
Jeffrey W.
The price is AU$311
includes taxes & fees
26 Jan - 27 Jan
Studio Queen in the heart of downtown.

Hot Tub - King Suite - Game Room - Large Groups

Hot Tub - King Suite - Game Room - Large Groups
Sun Prairie
10.0 out of 10, Exceptional, (16 reviews)
"We had a great visit "
United States
Jennifer D.
The price is AU$954
includes taxes & fees
14 Jan - 15 Jan
Hot Tub - King Suite - Game Room - Large Groups

1 Bedroom - 1220 Canterbury Ct

1 Bedroom - 1220 Canterbury Ct
Sun Prairie
The price is AU$420
includes taxes & fees
14 Jan - 15 Jan
1 Bedroom - 1220 Canterbury Ct

Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (37 reviews)
"Beautiful apartment with all we needed for a comfortable family July 4th weekend away!! "
United States
Mindi Z.
The price is AU$435
includes taxes & fees
20 Jan - 21 Jan
Doty ★ Walk to Everything -Hotel Quality- Downtown

Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.8 out of 10, Exceptional, (22 reviews)
"Everything was exactly as listed and the property was so beautiful. Came with some friends and will definitely try to come back soon! "
United States
Paul G.
The price is AU$588
includes taxes & fees
14 Jan - 15 Jan
Lakeview Cabin > Unique Mid-Century Tucked in Bluff

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

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Sun Prairie
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful spacious property, extremely clean and excellent host!"
United States
Jen F.
The price is AU$852
includes taxes & fees
14 Jan - 15 Jan
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

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

Private Pool - HOT TUB - Sauna - Game Room - Pets
Sun Prairie
10.0 out of 10, Exceptional, (10 reviews)
"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$1,181
includes taxes & fees
14 Jan - 15 Jan
Private Pool - HOT TUB - Sauna - Game Room - Pets
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$200 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.