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)
"Great stay at the Dylin"
United States
Lauri
$107 nightly
The price is $124
Jan 25 - Jan 26
Total with taxes and fees
The Dylin

Cannery Square Unit - 106 by Patriot Properties

Cannery Square Unit - 106 by Patriot Properties
Sun Prairie
9.4 out of 10, Exceptional, (27 reviews)
"Great place "
United States
Armando
$385 nightly
The price is $433
Feb 21 - Feb 22
Total with taxes and fees
Cannery Square Unit - 106 by Patriot Properties

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, (8 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.
$400 nightly
The price is $454
Feb 8 - Feb 9
Total with taxes and fees
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
$119 nightly
The price is $134
Jan 30 - Jan 31
Total with taxes and fees
Pool with Slide. Great for Business Travelers!

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

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
2.0 star property
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.
$274 nightly
The price is $303
Jan 25 - Jan 26
Total with taxes and fees
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

Cannery Square Short Term Rentals -104 by Patriot

Cannery Square Short Term Rentals -104 by Patriot
Sun Prairie
9.8 out of 10, Exceptional, (46 reviews)
"Roomy. Kitchen had basics. Good beds and pillows. "
United States
Susan
$287 nightly
The price is $323
Jan 27 - Jan 28
Total with taxes and fees
Cannery Square Short Term Rentals -104 by Patriot

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.
$359 nightly
The price is $404
Jan 24 - Jan 25
Total with taxes and fees
2 Bedroom - Main Street Sun Prairie WI

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.
$121 nightly
The price is $128
Feb 3 - Feb 4
Total with taxes and fees
Enjoy Nature with Full Comfort!

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
$139 nightly
The price is $157
Jan 30 - Jan 31
Total with taxes and fees
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

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.
$182 nightly
The price is $210
Jan 25 - Jan 26
Total with taxes and fees
Studio Queen in the heart of downtown.

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.
$124 nightly
The price is $141
Jan 29 - Jan 30
Total with taxes and fees
King Suite | Free Breakfast. Pool and Hot Tub

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.
$241 nightly
The price is $278
Jan 25 - Jan 26
Total with taxes and fees
Doty ★ Walk to Everything -Hotel Quality- 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, (267 reviews)
"Great place and the hosts were great!"
United States
Drew M.
$315 nightly
The price is $354
Jan 26 - Jan 27
Total with taxes and fees
A Pleasant Retreat- No Cleaning Fee & New Discounts

1 Bedroom - 1220 Canterbury Ct

1 Bedroom - 1220 Canterbury Ct
Sun Prairie
$251 nightly
The price is $282
Jan 25 - Jan 26
Total with taxes and fees
1 Bedroom - 1220 Canterbury Ct

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.
$439 nightly
The price is $498
Jan 25 - Jan 26
Total with taxes and fees
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.8 out of 10, Exceptional, (23 reviews)
"Everything was exactly as listed and the property was so beautiful. Came with some friends and will definitely try to come back soon! "
United States
Paul G.
$372 nightly
The price is $401
Feb 17 - Feb 18
Total with taxes and fees
Lakeview Cabin > Unique Mid-Century Tucked in Bluff

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.
$247 nightly
The price is $286
Jan 25 - Jan 26
Total with taxes and fees
Free Breakfast Pool & Hot Tub. Near UW-Madison

Waters Edge Cottage

Waters Edge Cottage
Merrimac
8.2 out of 10, Very Good, (11 reviews)
"Won $500 pull tab this weekend. Would stay again."
United States
Ryan R.
$452 nightly
The price is $509
Jan 24 - Jan 25
Total with taxes and fees
Waters Edge Cottage

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.
$507 nightly
The price is $570
Jan 24 - Jan 25
Total with taxes and fees
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

Winter Trail Access | Cozy Fireplace Haven

Winter Trail Access | Cozy Fireplace Haven
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.
$610 nightly
The price is $692
Jan 25 - Jan 26
Total with taxes and fees
Winter Trail Access | Cozy Fireplace Haven
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

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $124 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

A Pleasant Retreat- No Cleaning Fee & New Discounts: 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. 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. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.