A park with a statue of a figure on horseback, surrounded by leafless trees and a clear sky.

Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

1. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (214 reviews)
"Good location"
United States
ANCA
The price is NZ$226
includes taxes & fees
19 Nov - 20 Nov
The Dylin

2. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very good, (1 review)
The price is NZ$478
includes taxes & fees
23 Nov - 24 Nov
Studio Apartment at Cannery Square

3. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.6 out of 10, Exceptional, (56 reviews)
"Great and easy stay! The place was comfortable and inviting. Would stay again!"
United States
Taylor S.
The price is NZ$591
includes taxes & fees
8 Dec - 9 Dec
2 Bed, 2 Bath Apartment at Cannery Square

4. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.4 out of 10, Exceptional, (31 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
The price is NZ$595
includes taxes & fees
12 Nov - 13 Nov
2 Bed, 2 Bath Apartment at Cannery Square

5. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.4 out of 10, Very good, (16 reviews)
"Great location - able to walk to many stores and restaurants. Spacious for a studio and very quiet."
United States
Martha T.
Studio Apartment at Cannery Square

6. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (59 reviews)
"Enjoyed the county setting and seeing the cranes and hearing the rooster crow!"
United States
Elizabeth C.
The price is NZ$223
includes taxes & fees
1 Dec - 2 Dec
A Room with a View

7. Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool

Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
Madison
10.0 out of 10, Exceptional, (1 review)
"Clean, quiet, and convenient! Everything went smooth."
United States
Thomas C.
The price is NZ$440
includes taxes & fees
29 Nov - 30 Nov
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool

8. Escape to tranquility – your countryside haven, and at times with a horse or two

Escape to tranquility – your countryside haven, and at times with a horse or two
Dane
10.0 out of 10, Exceptional, (3 reviews)
"Feeding the horses was so fun and the scenery is very picturesque. Wonderful place to stay!"
United States
Katelyn F.
The price is NZ$472
includes taxes & fees
1 Dec - 2 Dec
Escape to tranquility – your countryside haven, and at times with a horse or two

9. 2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
Sun Prairie
9.6 out of 10, Exceptional, (43 reviews)
"The host was very responsive and very kind and considerate to our reason for traveling. The property was beautiful and clean inside and out, we really enjoyed our stay."
United States
Sha'Vonne G.
The price is NZ$673
includes taxes & fees
11 Nov - 12 Nov
2 Bedroom Apartment Downtown Sun Prairie!

10. King Suite | Free Breakfast. Pool and Hot Tub

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.4 out of 10, Very good, (7 reviews)
"Great place for a stay."
United States
Andy D.
The price is NZ$315
includes taxes & fees
6 Dec - 7 Dec
King Suite | Free Breakfast. Pool and Hot Tub

11. Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12
Sun Prairie
10.0 out of 10, Exceptional, (27 reviews)
"This was the perfect size home for a holiday family get together. Nice common spaces with enough areas to go when a little alone time was needed "
United States
Steve S.
The price is NZ$970
includes taxes & fees
10 Dec - 11 Dec
Entire 3 Bedroom with Fireplace - sleeps 12

12. 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, (26 reviews)
"It was a beautiful place and we love to be back!!!"
United States
Terri N.
The price is NZ$1,008
includes taxes & fees
29 Nov - 30 Nov
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

13. Capital City- 6 Miles from Madison with fireplace

Capital City- 6 Miles from Madison with fireplace
Sun Prairie
10.0 out of 10, Exceptional, (58 reviews)
"Great stay."
United States
Kevin M.
The price is NZ$1,034
includes taxes & fees
11 Nov - 12 Nov
Capital City- 6 Miles from Madison with fireplace

14. #3 Riverfront Lodging. Beach, Boat, Fish, Hike.

#3 Riverfront Lodging. Beach, Boat, Fish, Hike.
Poynette
The price is NZ$430
includes taxes & fees
6 Dec - 7 Dec
#3 Riverfront Lodging. Beach, Boat, Fish, Hike.

15. Free Breakfast. Pool & Hot Tub. Near East Towne Mall!

Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
Madison
The price is NZ$672
includes taxes & fees
6 Dec - 7 Dec
Free Breakfast. Pool & Hot Tub. Near East Towne Mall!

16. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is NZ$354
includes taxes & fees
12 Nov - 13 Nov
Pool with Slide. Great for Business Travelers!

17. Riverfront Lodging. Beach, hike, ski, explore, relax. #1

Riverfront Lodging. Beach, hike, ski, explore, relax. #1
Dekorra
The price is NZ$392
includes taxes & fees
16 Nov - 17 Nov
Riverfront Lodging. Beach, hike, ski, explore, relax. #1

18. Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Village of Cottage Grove
9.8 out of 10, Exceptional, (19 reviews)
"Everything was very nice"
United States
Anonymous traveller
The price is NZ$760
includes taxes & fees
16 Nov - 17 Nov
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

19. 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 NZ$410
includes taxes & fees
7 Dec - 8 Dec
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

20. Charming 3-bedroom house on Madison's Eastside! Close to everything!

Charming 3-bedroom house on Madison's Eastside! Close to everything!
Madison
The price is NZ$1,000
includes taxes & fees
11 Dec - 12 Dec
Charming 3-bedroom house on Madison's Eastside! Close to everything!
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Windsor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Windsor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Windsor. Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Windsor short-term rentals, that won’t be hard to do.

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?

Doty ★ Walk to Everything -Hotel Quality- Downtown: This holiday home rental outside of Windsor is located in the city centre, and has a balcony, a selection of games and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Windsor?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Windsor stay.

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.