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

Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Windsor vacation rentals

A gym with treadmills, elliptical machines, and free weights.

1. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.4 out of 10, Very Good, (16 reviews)
"Great little town to stay the night. Woke early 5:30 am to tow truck towing cars in front lot. We luckily parked in back lot as instructed. Other than the noise of this unfortunate event, we enjoyed our stay. Loved the town and many places to walk to. Pizza place was amazing!"
United States
Cheryl B.
The price is ￥18,126
￥43,245 total
includes taxes & fees
Sep 8 - Sep 9
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.

2. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.4 out of 10, Exceptional, (29 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
The price is ￥20,158
￥55,904 total
includes taxes & fees
Sep 8 - Sep 9
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.

3. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very Good, (1 review)
The price is ￥15,939
￥45,169 total
includes taxes & fees
Oct 7 - Oct 8
Studio Apartment at Cannery Square
A covered patio with outdoor furniture, a view of a red barn, and a grassy field.

4. 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, (2 reviews)
"Feeding the horses was so fun and the scenery is very picturesque. Wonderful place to stay!"
United States
Katelyn F.
The price is ￥23,283
￥39,197 total
includes taxes & fees
Sep 8 - Sep 9
Escape to tranquility – your countryside haven, and at times with a horse or two
A lobby with a wall displaying vintage advertisements, a sofa, a potted plant, and a window with blinds.

5. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.8 out of 10, Exceptional, (54 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 ￥25,470
￥62,583 total
includes taxes & fees
Sep 20 - Sep 21
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.

6. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (180 reviews)
"The freaking best place."
United States
Seth
The price is ￥19,927
￥23,016 total
includes taxes & fees
Sep 8 - Sep 9
The Dylin
A modern kitchen with a refrigerator, microwave, and bar stools.

7. 2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
Sun Prairie
9.6 out of 10, Exceptional, (41 reviews)
"This is the third time we have rented this property. Love the full kitchen and laundry! Comfy bed. Experience was great. Especially like the pizza shop on main level and coffe shop across the street!"
United States
Robert M.
The price is ￥30,158
￥63,638 total
includes taxes & fees
Sep 8 - Sep 9
2 Bedroom Apartment Downtown Sun Prairie!
A conference room with multiple tables and chairs, a projector screen, and a carpeted floor.

8. 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 ￥29,682
￥39,156 total
includes taxes & fees
Oct 4 - Oct 5
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
An outdoor patio with a brick grill and seating area.

9. 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 ￥21,201
￥27,900 total
includes taxes & fees
Sep 20 - Sep 21
King Suite | Free Breakfast. Pool and Hot Tub
A chalkboard sign with a welcome message and room instructions.

10. 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, (21 reviews)
"It was a beautiful place and we love to be back!!!"
United States
Terri N.
The price is ￥54,691
￥93,698 total
includes taxes & fees
Sep 8 - Sep 9
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
A hotel pantry with a refrigerator stocked with beverages, a microwave, and shelves with snacks and condiments.

11. Accessible 1BR Suite | Free Daily Breakfast & Pool

Accessible 1BR Suite | Free Daily Breakfast & Pool
Madison
The price is ￥29,533
￥38,985 total
includes taxes & fees
Oct 4 - Oct 5
Accessible 1BR Suite | Free Daily Breakfast & Pool
A sunroom with wicker furniture, large windows, and string lights.

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

Hot Tub - Game Room - 20 min to Capitol - Pets
Sun Prairie
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay! Thank you!!"
United States
Goodie A.
The price is ￥42,190
￥116,624 total
includes taxes & fees
Sep 8 - Sep 9
Hot Tub - Game Room - 20 min to Capitol - Pets

13. Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12
Sun Prairie
10.0 out of 10, Exceptional, (21 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 ￥58,598
￥98,797 total
includes taxes & fees
Sep 8 - Sep 9
Entire 3 Bedroom with Fireplace - sleeps 12
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.

14. Capital City- 6 Miles from Madison with fireplace

Capital City- 6 Miles from Madison with fireplace
Sun Prairie
10.0 out of 10, Exceptional, (54 reviews)
"Very nice place"
United States
Penny C.
The price is ￥62,817
￥104,949 total
includes taxes & fees
Sep 9 - Sep 10
Capital City- 6 Miles from Madison with fireplace
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
The price is ￥42,034
￥55,799 total
includes taxes & fees
Oct 4 - Oct 5
Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
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, (14 reviews)
"This property is the nicest property we have stayed in. Everything was there for our convenience. It was extremely pet friendly and very nicely furnished. We hope to stay there again."
United States
Donald V.
The price is ￥20,392
￥35,485 total
includes taxes & fees
Sep 10 - Sep 11
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
A kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window with blinds.

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

Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Village of Cottage Grove
10.0 out of 10, Exceptional, (17 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
The price is ￥28,502
￥78,640 total
includes taxes & fees
Oct 4 - Oct 5
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

18. 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 ￥13,782
￥21,134 total
includes taxes & fees
Sep 8 - Sep 9
A Room with a View
A modern living room with a fireplace, a flat-screen TV displaying 'NETFLIX', and a cozy seating arrangement.

19. Hot Tub - King Suite - Game Room - Large Groups

Hot Tub - King Suite - Game Room - Large Groups
Sun Prairie
10.0 out of 10, Exceptional, (24 reviews)
"An amazing house, great location, it was the most wonderfully supplied VRBO ever!"
United States
George P.
The price is ￥40,471
￥99,351 total
includes taxes & fees
Sep 17 - Sep 18
Hot Tub - King Suite - Game Room - Large Groups
A wooden dock leading to a house with a balcony, surrounded by trees and a body of water.

20. 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 ￥37,296
￥75,495 total
includes taxes & fees
Sep 21 - Sep 22
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to 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

Super 8 by Wyndham Madison South

Super 8 by Wyndham Madison South

8/10 Good
"Been here many times."
Wade 1-night trip
Posted less than an hour ago
Super 8 by Wyndham Madison South

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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?

LakeMonona Waterfront + PrivateDock + FencedYard + HotTub + GameRoom + EVCharger: You might want to consider this vacation home rental near Windsor, which is located on a lake and has a fireplace, a balcony, and a barbecue grill 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. It offers a garden, an arcade game room, and a hot tub so you can immerse yourself in your vacation.

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 Barrymore Theatre.

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.