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

Windsor Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Windsor vacation rentals

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.

1. 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 SAR 477
SAR 1,331 total
includes taxes & fees
6 Oct - 7 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 SAR 304
SAR 998 total
includes taxes & fees
5 Oct - 6 Oct
Studio Apartment at Cannery Square
A lobby with a wall displaying vintage advertisements, a sofa, a potted plant, and a window with blinds.

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, (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 SAR 477
SAR 1,322 total
includes taxes & fees
19 Oct - 20 Oct
2 Bed, 2 Bath Apartment at Cannery Square
A modern interior with a brown sofa, a round marble coffee table, and a decorative vase with flowers.

4. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (188 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 SAR 476
SAR 550 total
includes taxes & fees
28 Oct - 29 Oct
The Dylin
A covered patio with outdoor furniture, a view of a red barn, and a grassy field.

5. 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 SAR 556
SAR 904 total
includes taxes & fees
11 Oct - 12 Oct
Escape to tranquility – your countryside haven, and at times with a horse or two
A modern kitchen with a refrigerator, microwave, and bar stools.

6. 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 SAR 725
SAR 1,521 total
includes taxes & fees
5 Oct - 6 Oct
2 Bedroom Apartment Downtown Sun Prairie!
An outdoor seating area with wicker furniture and a central fire feature.

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 SAR 751
SAR 993 total
includes taxes & fees
4 Oct - 5 Oct
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
A chalkboard sign with a welcome message and room instructions.

8. 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 SAR 1,314
SAR 2,243 total
includes taxes & fees
4 Oct - 5 Oct
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
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)
"Great, comfortable stay. And close to shopping, which is just what I like to do! "
United States
Joyana A.
The price is SAR 1,509
SAR 2,517 total
includes taxes & fees
4 Oct - 5 Oct
Capital City- 6 Miles from Madison with fireplace
Master Bedroom /King bed

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 SAR 1,408
SAR 2,365 total
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 SAR 509
SAR 670 total
includes taxes & fees
4 Oct - 5 Oct
King Suite | Free Breakfast. Pool and Hot Tub
A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

12. 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 SAR 301
SAR 476 total
includes taxes & fees
12 Oct - 13 Oct
A Room with a View
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 SAR 590
SAR 1,769 total
includes taxes & fees
27 Oct - 28 Oct
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
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.

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

Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
Madison
The price is SAR 1,235
SAR 1,537 total
includes taxes & fees
4 Oct - 5 Oct
Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
A dining area with a wooden table and chairs, a window with blinds, and a view of a wooden fence.

15. #4 Riverfront Lodging. Beach, Boat, Fish, Hike.

#4 Riverfront Lodging. Beach, Boat, Fish, Hike.
Poynette
10.0 out of 10, Exceptional, (1 review)
"Amazing view, clean stay and pet friendly for those with fur babies. Will definitely be coming back!"
United States
Miranda
The price is SAR 575
SAR 986 total
includes taxes & fees
1 Oct - 2 Oct
#4 Riverfront Lodging. Beach, Boat, Fish, Hike.
A spacious living area with a wooden floor, a round mirror on the wall, and a dark-colored sofa.

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

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Middleton
10.0 out of 10, Exceptional, (16 reviews)
"Beautiful place, great stay."
United States
Thomas D.
The price is SAR 578
SAR 1,074 total
includes taxes & fees
25 Oct - 26 Oct
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
A deck with a table and chairs, overlooking a grassy area with trees and a body of water.

17. Riverfront Lodging. Beach, hike, ski, explore, relax. #2

Riverfront Lodging. Beach, hike, ski, explore, relax. #2
Dekorra
10.0 out of 10, Exceptional, (1 review)
"Great stay for our fishing trip"
United States
Brian S.
The price is SAR 587
SAR 999 total
includes taxes & fees
5 Oct - 6 Oct
Riverfront Lodging. Beach, hike, ski, explore, relax. #2
A wooden dock leading to a house with a balcony, surrounded by trees and a body of water.

18. 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 SAR 896
SAR 1,857 total
includes taxes & fees
12 Oct - 13 Oct
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
A spacious dining area with a high ceiling and large windows, wooden furniture, and a view of the outdoors.

19. Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.6 out of 10, Exceptional, (30 reviews)
"Great Place Beautiful landscape from the deckHost was very responsive Would go back again in a heartbeat Everything you need for a great stay"
United States
John W.
The price is SAR 730
SAR 1,509 total
includes taxes & fees
27 Oct - 28 Oct
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

20. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is SAR 562
SAR 732 total
includes taxes & fees
4 Oct - 5 Oct
Pool with Slide. Great for Business Travelers!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

La Quinta Inn & Suites by Wyndham Madison American Center

La Quinta Inn & Suites by Wyndham Madison American Center

10/10 Excellent
"Awesome"
Zehara 1-night trip
Posted less than an hour ago
La Quinta Inn & Suites by Wyndham Madison American Center

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, we give you a choice of vacation rentals in Windsor close to Mousehouse Cheesehaus, or you can go with a more remote option if you'd like a relaxing place to stay. Our travelers 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's the top vacation rental that Windsor has to offer?

Doty ★ Walk to Everything -Hotel Quality- Downtown: Visitors like this Windsor vacation home rental. It is located in the city center 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 you can cook with friends or family.

How many vacation rentals are there in Windsor?

With 3 Expedia vacation rentals, you're sure 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 larger area, you’ll find East Towne Mall and Madison Area Technical College.

What are vacation rentals like in Windsor?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Windsor. Vacation rentals offer amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for family gatherings.