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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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Windsor holiday rentals

A lobby with a wall displaying vintage advertisements, a sofa, a potted plant, and a window with blinds.

1. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.6 out of 10, Exceptional, (55 reviews)
"This was our third or fourth year staying there while visiting family for the holidays. Comfy beds, great location!"
United States
Sara M.
The price is NZ$628
includes taxes & fees
25 Oct - 26 Oct
2 Bed, 2 Bath Apartment at Cannery Square
A modern kitchen with a microwave, stove, and bar stools. There is a green sofa and a small table with a remote control.

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$467
includes taxes & fees
4 Oct - 5 Oct
Studio Apartment at Cannery Square
A modern kitchen with a dishwasher, a dining area with a table and chairs, a living room with a sofa and a TV, and a ceiling fan.

3. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.4 out of 10, Exceptional, (30 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
The price is NZ$616
includes taxes & fees
4 Oct - 5 Oct
2 Bed, 2 Bath Apartment at Cannery Square
An outdoor seating area with wicker furniture and a central fire feature.

4. 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$459
includes taxes & fees
4 Oct - 5 Oct
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
A modern kitchen with a refrigerator, microwave, and bar stools.

5. 2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
Sun Prairie
9.6 out of 10, Exceptional, (41 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$721
includes taxes & fees
5 Oct - 6 Oct
2 Bedroom Apartment Downtown Sun Prairie!
A modern interior with a brown sofa, a round marble coffee table, and a decorative vase with flowers.

6. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (187 reviews)
"The Dylan was a great location for us and we were very pleased with the garage parking, new modern finishes and the communication of the host. The unit had everything we needed for a super comfortable stay including a full kitchen and washer/dryer. No wasted space. Good arrangement in this two bedroom unit for 2 couples. Would stay here again and recommend."
United States
Debbie
The price is NZ$239
includes taxes & fees
25 Oct - 26 Oct
The Dylin
A chalkboard sign with a welcome message and room instructions.

7. 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, (23 reviews)
"It was a beautiful place and we love to be back!!!"
United States
Terri N.
The price is NZ$1,043
includes taxes & fees
29 Sept - 30 Sept
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
A covered patio with outdoor furniture, a view of a red barn, and a grassy field.

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$431
includes taxes & fees
13 Oct - 14 Oct
Escape to tranquility – your countryside haven, and at times with a horse or two
A bedroom with a dark grey wall, a bed with a striped bedspread, multiple pillows, a small side table with a vase and a lamp, and two framed botanical prints on the wall.

9. Capital City- 6 Miles from Madison with fireplace

Capital City- 6 Miles from Madison with fireplace
Sun Prairie
10.0 out of 10, Exceptional, (56 reviews)
"Very nice place"
United States
Penny C.
The price is NZ$1,160
includes taxes & fees
27 Sept - 28 Sept
Capital City- 6 Miles from Madison with fireplace

10. Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12
Sun Prairie
10.0 out of 10, Exceptional, (24 reviews)
"Tami was a wonderful host! Check in was fast and she was easy to communicate with. The house was clean and spacious."
United States
Joanna C.
The price is NZ$1,085
includes taxes & fees
4 Oct - 5 Oct
Entire 3 Bedroom with Fireplace - sleeps 12
An outdoor patio with a brick grill and seating area.

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

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.0 out of 10, Very good, (6 reviews)
"Great place for a stay."
United States
Andy D.
The price is NZ$315
includes taxes & fees
4 Oct - 5 Oct
King Suite | Free Breakfast. Pool and Hot Tub
A hotel room with a bed, a desk, a lamp, a framed picture, a kitchen area with cabinets and a microwave, and a carpeted floor.

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

Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
Madison
The price is NZ$768
includes taxes & fees
4 Oct - 5 Oct
Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

13. 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)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
The price is NZ$843
includes taxes & fees
26 Oct - 27 Oct
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

14. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (54 reviews)
"Beautiful view and pet friendly!"
United States
Ashley J.
The price is NZ$219
includes taxes & fees
29 Sept - 30 Sept
A Room with a View
A hotel room with a bed, a desk, a lamp, a framed picture, a kitchen area with cabinets and a microwave, and a carpeted floor.

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

Free Breakfast Pool & Hot Tub. Near East Towne Mall!
Madison
10.0 out of 10, Exceptional, (1 review)
"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 NZ$768
includes taxes & fees
4 Oct - 5 Oct
Free Breakfast Pool & Hot Tub. Near East Towne Mall!
A wooden dock leading to a house with a balcony, surrounded by trees and a body of water.

16. 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, (56 reviews)
"Great little lake house, close to downtown Madison. "
United States
LiHsin C.
The price is NZ$918
includes taxes & fees
26 Oct - 27 Oct
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
A grassy area with a tree, a small rock formation, and a distant structure.

17. #3 Riverfront Lodging. Beach, Boat, Fish, Hike.

#3 Riverfront Lodging. Beach, Boat, Fish, Hike.
Poynette
The price is NZ$502
includes taxes & fees
1 Oct - 2 Oct
#3 Riverfront Lodging. Beach, Boat, Fish, Hike.
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

18. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is NZ$340
includes taxes & fees
4 Oct - 5 Oct
Pool with Slide. Great for Business Travelers!
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

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$380
includes taxes & fees
22 Oct - 23 Oct
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
A hallway with wooden paneling, a framed welcome sign, and a door leading to a room.

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

Riverfront Lodging. Beach, hike, ski, explore, relax. #1
Dekorra
The price is NZ$504
includes taxes & fees
1 Oct - 2 Oct
Riverfront Lodging. Beach, hike, ski, explore, relax. #1
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

The Edgewater

The Edgewater

10/10 Excellent
"Nice quite get away, with great lake views and access"
David 3-night trip
Posted 7 hours ago
The Edgewater

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$219 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?

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.