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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Our top choices for Windsor vacation rentals

Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
The price is CA $141
CA $340 total
includes taxes & fees
Jun 29 - Jun 30
Studio Apartment at Cannery Square

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 CA $187
CA $247 total
includes taxes & fees
Jun 28 - Jun 29
King Suite | Free Breakfast. Pool and Hot Tub

Enjoy Nature with Full Comfort!

Enjoy Nature with Full Comfort!
Verona
9.2 out of 10, Wonderful, (44 reviews)
"We were visiting friends in the area and it was a perfect spot to stay."
United States
Christine U.
The price is CA $128
CA $195 total
includes taxes & fees
Jun 28 - Jun 29
Enjoy Nature with Full Comfort!

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, (7 reviews)
"This stay was truly perfect! Our hosts thought of every single detail and more. The property was perfectly appointed with all the little touches that made it ideal for a quiet couple's getaway just outside Madison. We drove nearly 8 hours north from Kansas City to get here, so imagine how wonderful it was to walk into a warm, cozy, welcoming house that had snacks on hand and a pizza delivery number front and center waiting for us! Best part of all - it was dog-friendly! Our dog immediately felt...
United States
Heather P.
The price is CA $194
CA $335 total
includes taxes & fees
Jun 30 - Jul 1
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

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 CA $274
CA $575 total
includes taxes & fees
Jun 29 - Jun 30
2 Bedroom Apartment Downtown Sun Prairie!

Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.0 out of 10, Very good, (13 reviews)
"Was cute neighborhood and everything was very clean and close by"
United States
Bri
The price is CA $165
CA $394 total
includes taxes & fees
Jun 30 - Jul 1
Studio Apartment at Cannery Square

Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.8 out of 10, Exceptional, (28 reviews)
"We had a great time and hope to return soon!"
United States
Jenna R.
The price is CA $311
CA $643 total
includes taxes & fees
Jul 1 - Jul 2
Lakeview Cabin > Unique Mid-Century Tucked in Bluff

2 Bed/ 2 Bath At Cannery Square

2 Bed/ 2 Bath At Cannery Square
Sun Prairie
9.6 out of 10, Exceptional, (50 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 CA $224
CA $517 total
includes taxes & fees
Jul 14 - Jul 15
2 Bed/ 2 Bath At Cannery Square

Hot Tub - King Suite - Game Room - Large Groups

Hot Tub - King Suite - Game Room - Large Groups
Sun Prairie
10.0 out of 10, Exceptional, (20 reviews)
"An amazing house, great location, it was the most wonderfully supplied VRBO ever!"
United States
George P.
The price is CA $419
CA $1,195 total
includes taxes & fees
Jul 1 - Jul 2
Hot Tub - King Suite - Game Room - Large Groups

Cozy Cabin on Crooked Lane close to Lake Wisconsin

Cozy Cabin on Crooked Lane close to Lake Wisconsin
Poynette
8.0 out of 10, Very good, (2 reviews)
"Pet friendly cabin in the woods. Mostly updated and nice for 4-6 people. We stayed with our dogs and it worked well for us. "
United States
Jon A.
The price is CA $330
CA $526 total
includes taxes & fees
Jul 27 - Jul 28
Cozy Cabin on Crooked Lane close to Lake Wisconsin

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is CA $186
CA $243 total
includes taxes & fees
Jun 28 - Jun 29
Pool with Slide. Great for Business Travelers!

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, (1 review)
"We had a great stay! Everything was as advertised and the sunset on the patio was the highlight."
United States
Michelle M.
The price is CA $256
CA $408 total
includes taxes & fees
Jun 29 - Jun 30
Escape to tranquility – your countryside haven, and at times with a horse or two

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 CA $215
CA $276 total
includes taxes & fees
Jun 28 - Jun 29
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

The Dylin

The Dylin
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (154 reviews)
"nice location"
United States
Mary
The price is CA $186
CA $215 total
includes taxes & fees
Jun 30 - Jul 1
The Dylin

Waters Edge Cottage

Waters Edge Cottage
Merrimac
8.0 out of 10, Very good, (14 reviews)
"Won $500 pull tab this weekend. Would stay again."
United States
Ryan R.
The price is CA $352
CA $723 total
includes taxes & fees
Jun 29 - Jun 30
Waters Edge Cottage

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, (8 reviews)
"Host was very attentive and property was clean, comfortable, and met the description. We would choose this accommodation again if we return to the area. "
United States
Amy M.
The price is CA $449
CA $1,271 total
includes taxes & fees
Jun 30 - Jul 1
Hot Tub - Game Room - 20 min to Capitol - Pets

Badger Digs - A Lofted Condo on the Wisconsin River

Badger Digs - A Lofted Condo on the Wisconsin River
Poynette
10.0 out of 10, Exceptional, (19 reviews)
"What a great place to stay for just a couple or a family! The host was so easy to communicate with and we had a wonderful time! "
United States
Heather B.
The price is CA $359
CA $593 total
includes taxes & fees
Jul 8 - Jul 9
Badger Digs - A Lofted Condo on the Wisconsin River

Fisher's Flop - A Lofted Condo on the Wisconsin River

Fisher's Flop - A Lofted Condo on the Wisconsin River
Poynette
10.0 out of 10, Exceptional, (13 reviews)
"The property is perfect.Jacuzzi tub, very comfy beds, nice porch space,And many other amenities.Owners are very accommodating and great at communication."
United States
Mary H.
The price is CA $369
CA $605 total
includes taxes & fees
Jul 21 - Jul 22
Fisher's Flop - A Lofted Condo on the Wisconsin River

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, (13 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
The price is CA $339
CA $826 total
includes taxes & fees
Jul 15 - Jul 16
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

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

Private Pool - Hot Tub - Sauna - Game Room - Pets
Sun Prairie
10.0 out of 10, Exceptional, (15 reviews)
"Great place for large group gatherings. Communication with our host was amazing. Highly recommend."
United States
Anonymous traveller
The price is CA $918
CA $1,999 total
includes taxes & fees
Jun 30 - Jul 1
Private Pool - Hot Tub - Sauna - Game Room - Pets
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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?

Amazing townhouse, amazing attractions, amazing city!: Visitors like this Windsor vacation home rental. It offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.