Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

Cannery Square Short Term Rentals

Cannery Square Short Term Rentals
Sun Prairie
9.4 out of 10, Exceptional, (28 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
$287 nightly
The price is $323
May 17 - May 18
Total with taxes and fees
Cannery Square Short Term Rentals

Cannery Square Short Term Rentals

Cannery Square Short Term Rentals
Sun Prairie
$219 nightly
The price is $232
May 10 - May 11
Total with taxes and fees
Cannery Square Short Term Rentals

2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
Sun Prairie
9.6 out of 10, Exceptional, (40 reviews)
"The host was very responsive and very kind and considerate to our reason for traveling. The property was beautiful and clean inside and out, we really enjoyed our stay."
United States
Sha'Vonne G.
$362 nightly
The price is $407
May 11 - May 12
Total with taxes and fees
2 Bedroom Apartment Downtown Sun Prairie!

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, (3 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.
$207 nightly
The price is $229
May 10 - May 11
Total with taxes and fees
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

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.
$152 nightly
The price is $173
May 17 - May 18
Total with taxes and fees
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, (41 reviews)
"We were visiting friends in the area and it was a perfect spot to stay."
United States
Christine U.
$128 nightly
The price is $135
May 26 - May 27
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
$168 nightly
The price is $190
May 14 - May 15
Total with taxes and fees
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

Waters Edge Cottage

Waters Edge Cottage
Merrimac
7.8 out of 10, Good, (12 reviews)
"Won $500 pull tab this weekend. Would stay again."
United States
Ryan R.
$455 nightly
The price is $512
May 10 - May 11
Total with taxes and fees
Waters Edge Cottage

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.
$268 nightly
The price is $283
May 13 - May 14
Total with taxes and fees
Cozy Cabin on Crooked Lane close to Lake Wisconsin

Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful house! We loved the basement game room and found our stay very comfortable. "
United States
Anonymous traveler
$417 nightly
The price is $449
May 11 - May 12
Total with taxes and fees
Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Cannery Square Short Term Rentals

Cannery Square Short Term Rentals
Sun Prairie
9.6 out of 10, Exceptional, (48 reviews)
"This was our third or fourth year staying there while visiting family for the holidays. Comfy beds, great location!"
United States
Sara M.
$284 nightly
The price is $320
May 10 - May 11
Total with taxes and fees
Cannery Square Short Term Rentals

1 Bedroom Apartment at Canterbury Court

1 Bedroom Apartment at Canterbury Court
Sun Prairie
10.0 out of 10, Exceptional, (1 review)
"Great for what our trip was for. Quiet. Pet friendly. Good location"
United States
Robert M.
$252 nightly
The price is $284
May 11 - May 12
Total with taxes and fees
1 Bedroom Apartment at Canterbury Court

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
$159 nightly
The price is $180
May 10 - May 11
Total with taxes and fees
Pool with Slide. Great for Business Travelers!

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, (11 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
$429 nightly
The price is $487
May 11 - May 12
Total with taxes and fees
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

Cannery Square Short Term Rentals

Cannery Square Short Term Rentals
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
$246 nightly
The price is $277
May 11 - May 12
Total with taxes and fees
Cannery Square Short Term Rentals

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, (52 reviews)
"The location is wonderful. The river setting is beautiful. The pelicans are so fun to watch. Enjoyed all the rooms with tvs."
United States
Robert
$442 nightly
The price is $501
May 11 - May 12
Total with taxes and fees
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

The Dylin

The Dylin
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (139 reviews)
"Small apartment for the price of a regular hotel room! Great decor 😎"
United States
jonathan
$134 nightly
The price is $155
Jun 7 - Jun 8
Total with taxes and fees
The Dylin

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, (14 reviews)
"Beautiful spacious property, extremely clean and excellent host!"
United States
Jen F.
$507 nightly
The price is $570
May 10 - May 11
Total with taxes and fees
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

Madison Blooms | 3BR Escape

Madison Blooms | 3BR Escape
Fitchburg
10.0 out of 10, Exceptional, (23 reviews)
"We enjoyed staying here. VERY nice house, easy access, clean, a lot of space, no issues. We would book here again!"
United States
Liz A.
$727 nightly
The price is $825
May 11 - May 12
Total with taxes and fees
Madison Blooms | 3BR Escape

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.
$237 nightly
The price is $275
May 17 - May 18
Total with taxes and fees
Free Breakfast Pool & Hot Tub. Near UW-Madison
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 $135 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?

Beautifully remodeled 2 bed 104 Berkley Verona #6: You might want to consider this vacation home rental near Windsor, which has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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 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.