Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

The Dylin

The Dylin
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (123 reviews)
"Check in was easy, the room was super clean and cute, great amenities, close to the Sylvee and other bars/restaurants and the lake. Would stay again!! "
United States
Caitlin
The price is CA $156
CA $181 total
includes taxes & fees
Feb 23 - Feb 24
The Dylin

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is CA $147
CA $198 total
includes taxes & fees
Feb 22 - Feb 23
Pool with Slide. Great for Business Travelers!

Charming 3-bedroom Duplex unit with WiFi in Cottage Grove

Charming 3-bedroom Duplex unit with WiFi in Cottage Grove
Village of Cottage Grove
10.0 out of 10, Exceptional, (9 reviews)
"Stayed with friends for the weekend and really enjoyed the home. It was comfortable and had great amenities for our group!"
United States
Anakin F.
The price is CA $199
CA $629 total
includes taxes & fees
Feb 16 - Feb 17
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove

Cannery Square Short Term Rentals -104 by Patriot

Cannery Square Short Term Rentals -104 by Patriot
Sun Prairie
9.6 out of 10, Exceptional, (47 reviews)
"Roomy. Kitchen had basics. Good beds and pillows. "
United States
Susan
The price is CA $174
CA $438 total
includes taxes & fees
Feb 8 - Feb 9
Cannery Square Short Term Rentals -104 by Patriot

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 $164
CA $216 total
includes taxes & fees
Feb 22 - Feb 23
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

Enjoy Nature with Full Comfort!

Enjoy Nature with Full Comfort!
Verona
9.2 out of 10, Wonderful, (39 reviews)
"Clean very friendly nice spot"
Canada
Oliver H.
The price is CA $111
CA $175 total
includes taxes & fees
Feb 19 - Feb 20
Enjoy Nature with Full Comfort!

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 $141
CA $193 total
includes taxes & fees
Feb 15 - Feb 16
King Suite | Free Breakfast. Pool and Hot Tub

Cannery Square Short Term Rentals -102 by Patriot

Cannery Square Short Term Rentals -102 by Patriot
Sun Prairie
8.0 out of 10, Very good, (12 reviews)
"Was cute neighborhood and everything was very clean and close by"
United States
Bri
The price is CA $159
CA $378 total
includes taxes & fees
Mar 3 - Mar 4
Cannery Square Short Term Rentals -102 by Patriot

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, (2 reviews)
"We had a fantastic stay at this property, and it truly exceeded our expectations. The location is excellent—perfectly situated with convenient access to both the east and west sides of Madison, making it easy to get wherever we needed to go. The owners were incredibly helpful and responsive, answering the few questions we had quickly and kindly, which made the entire experience even smoother.One of the biggest highlights for us was the private fenced-in area, which was absolutely perfect for our...
United States
Jessi P.
The price is CA $196
CA $416 total
includes taxes & fees
Mar 5 - Mar 6
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (37 reviews)
"Very convenient"
United States
Joe R.
The price is CA $233
CA $393 total
includes taxes & fees
Feb 8 - Feb 9
Doty ★ Walk to Everything -Hotel Quality- Downtown

Studio Queen in the heart of downtown.

Studio Queen in the heart of downtown.
Downtown Madison
10.0 out of 10, Exceptional, (1 review)
"Convenient location for events on the Capital Square, State Street and UW-Madison Campus."
United States
Jeffrey W.
The price is CA $204
CA $267 total
includes taxes & fees
Mar 5 - Mar 6
Studio Queen in the heart of downtown.

2 Bedroom - Main Street Sun Prairie WI

2 Bedroom - Main Street Sun Prairie WI
Sun Prairie
9.6 out of 10, Exceptional, (38 reviews)
"Clean and quiet. Nice neighborhood amenities. "
United States
Mark L.
The price is CA $264
CA $554 total
includes taxes & fees
Feb 9 - Feb 10
2 Bedroom - Main Street Sun Prairie WI

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, (47 reviews)
"It was lovely to be by the lake and have the view from the living room along with gas fireplace. So relaxing even in the off season."
United States
Justine K.
The price is CA $326
CA $682 total
includes taxes & fees
Feb 8 - Feb 9
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

A Pleasant Retreat- No Cleaning Fee & New Discounts

A Pleasant Retreat- No Cleaning Fee & New Discounts
Sun Prairie
10.0 out of 10, Exceptional, (269 reviews)
"Great place and the hosts were great!"
United States
Drew M.
The price is CA $376
CA $478 total
includes taxes & fees
Feb 8 - Feb 9
A Pleasant Retreat- No Cleaning Fee & New Discounts

Free Breakfast Pool & Hot Tub. Near UW-Madison

Free Breakfast Pool & Hot Tub. Near UW-Madison
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 CA $302
CA $401 total
includes taxes & fees
Feb 12 - Feb 13
Free Breakfast Pool & Hot Tub. Near UW-Madison

Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.8 out of 10, Exceptional, (25 reviews)
"Beautiful property with a perfect view for fall color. Very comfortable and great space for both couples and family. We enjoyed a very relaxing stay. Host was very prompt with responses and easy to work with."
United States
Jenel S.
The price is CA $208
CA $508 total
includes taxes & fees
Feb 25 - Feb 26
Lakeview Cabin > Unique Mid-Century Tucked in Bluff

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, (13 reviews)
"Beautiful spacious property, extremely clean and excellent host!"
United States
Jen F.
The price is CA $451
CA $783 total
includes taxes & fees
Feb 8 - Feb 9
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12
Sun Prairie
9.8 out of 10, Exceptional, (16 reviews)
"The beds were super comfortable and the house had a lot of space. Tami was very helpful and communicative with the check in and check out process."
United States
Noah D.
The price is CA $479
CA $818 total
includes taxes & fees
Feb 8 - Feb 9
Entire 3 Bedroom with Fireplace - sleeps 12

Snowy Madison Escape | Warm Executive Home

Snowy Madison Escape | Warm Executive Home
Fitchburg
10.0 out of 10, Exceptional, (20 reviews)
"Property was generally clean, spacious and had all the amenities that our family needed.An enjoyable stay at a nice property!"
United States
Kim & Jeff T.
The price is CA $334
CA $947 total
includes taxes & fees
Feb 9 - Feb 10
Snowy Madison Escape | Warm Executive Home

Capital PrimeTime - 6 Miles from Madison w/ fireplace

Capital PrimeTime - 6 Miles from Madison w/ fireplace
Sun Prairie
9.8 out of 10, Exceptional, (36 reviews)
"Would recommend - very good location, nice space, and great host!"
United States
James O.
The price is CA $513
CA $862 total
includes taxes & fees
Feb 8 - Feb 9
Capital PrimeTime - 6 Miles from Madison w/ fireplace
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?

ONE OF A KIND vacation rental with a view: Visitors like this Windsor vacation home rental. It offers a fireplace, a furnished patio, 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.

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.