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
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Windsor vacation rentals

Interior

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, (28 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
The price is AED 489
AED 1,339 total
includes taxes & fees
31 Aug - 1 Sep
2 Bed, 2 Bath Apartment at Cannery Square
Fitness facility

2. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.4 out of 10, Very Good, (15 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 AED 426
AED 1,021 total
includes taxes & fees
6 Sep - 7 Sep
Studio Apartment at Cannery Square
Interior

3. 2 Bed, 2 Bath Apartment at Cannery Square

2 Bed, 2 Bath Apartment at Cannery Square
Sun Prairie
9.8 out of 10, Exceptional, (53 reviews)
"Clean and comfortable, good location, attentive host. If you are staying longer than one night, bring extra toilet paper, bring paper towels and trash bags, and sheets for the pull-out sofa if you plan to use it."
United States
Angela C.
The price is AED 466
AED 1,310 total
includes taxes & fees
25 Aug - 26 Aug
2 Bed, 2 Bath Apartment at Cannery Square
Sauna

4. Cozy 1 Bedroom Apartment with King Bed & Patio Near Madison

Cozy 1 Bedroom Apartment with King Bed & Patio Near Madison
Sun Prairie
8.0 out of 10, Very Good, (2 reviews)
"Great for what our trip was for. Quiet. Pet friendly. Good location"
United States
Robert M.
The price is AED 426
AED 1,256 total
includes taxes & fees
2 Sep - 3 Sep
Cozy 1 Bedroom Apartment with King Bed & Patio Near Madison
Reception

5. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (177 reviews)
"nice location"
United States
Mary
The price is AED 493
AED 569 total
includes taxes & fees
7 Sep - 8 Sep
The Dylin
Dining

6. 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 AED 683
AED 903 total
includes taxes & fees
6 Sep - 7 Sep
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
Coffee/tea maker, fridge, microwave, oven

7. 2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
Sun Prairie
9.6 out of 10, Exceptional, (40 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 AED 709
AED 1,504 total
includes taxes & fees
31 Aug - 1 Sep
2 Bedroom Apartment Downtown Sun Prairie!
Outdoor dining

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, (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 AED 680
AED 1,092 total
includes taxes & fees
14 Sep - 15 Sep
Escape to tranquility – your countryside haven, and at times with a horse or two
TV, offices

9. Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
The price is AED 668
AED 1,438 total
includes taxes & fees
25 Aug - 26 Aug
Studio Apartment at Cannery Square
Interior

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 AED 1,286
AED 2,219 total
includes taxes & fees
25 Aug - 26 Aug
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Terrace/patio

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, (5 reviews)
"Great place for a stay."
United States
Andy D.
The price is AED 501
AED 659 total
includes taxes & fees
6 Sep - 7 Sep
King Suite | Free Breakfast. Pool and Hot Tub
Interior

12. 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 AED 1,031
AED 1,366 total
includes taxes & fees
20 Sep - 21 Sep
Free Breakfast Pool & Hot Tub. Near East Towne Mall!
4 bedrooms, iron/ironing board, WiFi (free), bed sheets

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, (52 reviews)
"Very nice place"
United States
Penny C.
The price is AED 1,477
AED 2,467 total
includes taxes & fees
25 Aug - 26 Aug
Capital City- 6 Miles from Madison with fireplace
3 bedrooms, WiFi (free), bed sheets

14. 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 AED 1,377
AED 2,339 total
includes taxes & fees
25 Aug - 26 Aug
Entire 3 Bedroom with Fireplace - sleeps 12
Coffee/tea maker, fridge, microwave, oven

15. 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, (15 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
The price is AED 577
AED 1,752 total
includes taxes & fees
2 Sep - 3 Sep
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Smart TV, computer monitors

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 AED 516
AED 886 total
includes taxes & fees
14 Sep - 15 Sep
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Pool

17. Private Pool - Hot Tub - Sauna - Game Room - Pets

Private Pool - Hot Tub - Sauna - Game Room - Pets
Sun Prairie
9.8 out of 10, Exceptional, (20 reviews)
"Perfect getaway spot for the whole family"
United States
allison s.
The price is AED 1,895
AED 4,231 total
includes taxes & fees
25 Aug - 26 Aug
Private Pool - Hot Tub - Sauna - Game Room - Pets
Pool

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

Private Pool - Hot Tub - Game Room - 20 min DT
Sun Prairie
10.0 out of 10, Exceptional, (11 reviews)
"We had a great family weekend in a great home that had plenty of space for all 12 of us. It was clean and the host was very accommodating and responsive. We will definitely look to stay there again on our next ski adventure. "
United States
Kylie V.
The price is AED 1,396
AED 3,415 total
includes taxes & fees
25 Aug - 26 Aug
Private Pool - Hot Tub - Game Room - 20 min DT
Outdoor dining

19. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (53 reviews)
"Beautiful view and pet friendly!"
United States
Ashley J.
The price is AED 364
AED 539 total
includes taxes & fees
22 Sep - 23 Sep
A Room with a View
Exterior

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 AED 907
AED 1,892 total
includes taxes & fees
2 Sep - 3 Sep
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

AmericInn by Wyndham Madison West

AmericInn by Wyndham Madison West

8/10 Good
"Very clean and great staff, very closely to everything"
Raymundo 3-night trip
Posted 2 hours ago
AmericInn by Wyndham Madison West

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?

Paoli Den - Renovated Flat!: You might want to consider this vacation home rental near Windsor, which offers a patio, a garden, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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.