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Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

Aparthotel in Tenney-Lapham

The Dylin
4.0 star property
9.4 out of 10, Exceptional, (123 reviews)
"Great stay at the Dylin"
United States
Lauri
$112 nightly
The price is $129
Jan 18 - Jan 19
Total with taxes and fees
The Dylin
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"I had an excellent stay with Kingdom Hospitality. The home was immaculate, and I enjoyed the updated kitchen. The hot tub was clean, and a great amenity for stress relief. "
United States
Trey B.
Hot Tub - Game Room - 20 min to Capitol - Pets
9.2 out of 10, Wonderful, (39 reviews)
"Clean very friendly nice spot"
Canada
Oliver H.
$121 nightly
The price is $128
Jan 18 - Jan 19
Total with taxes and fees
Enjoy Nature with Full Comfort!
9.8 out of 10, Exceptional, (46 reviews)
"Roomy. Kitchen had basics. Good beds and pillows. "
United States
Susan
$284 nightly
The price is $320
Jan 13 - Jan 14
Total with taxes and fees
Cannery Square Short Term Rentals -104 by Patriot

Vacation Home in Village of Cottage Grove

Charming 3-bedroom Duplex unit with WiFi in 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.
$391 nightly
The price is $443
Jan 13 - Jan 14
Total with taxes and fees
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove
9.6 out of 10, Exceptional, (37 reviews)
"Clean and quiet. Nice neighborhood amenities. "
United States
Mark L.
$359 nightly
The price is $404
Jan 13 - Jan 14
Total with taxes and fees
2 Bedroom - Main Street Sun Prairie WI
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"The house was clean, large, and nicely decorated. It felt welcoming and homey. The host was friendly and responsive to our questions. "
United States
Ellen M.
$666 nightly
The price is $731
Jan 13 - Jan 14
Total with taxes and fees
Hot Tub - Private Pool - Game Room - 20 min DT
$120 nightly
The price is $136
Jan 30 - Jan 31
Total with taxes and fees
Pool with Slide. Great for Business Travelers!
8.0 out of 10, Very Good, (12 reviews)
"Was cute neighborhood and everything was very clean and close by"
United States
Bri
$244 nightly
The price is $275
Feb 1 - Feb 2
Total with taxes and fees
Cannery Square Short Term Rentals -102 by Patriot
8.0 out of 10, Very Good, (5 reviews)
"Great place for a stay."
United States
Andy D.
$124 nightly
The price is $142
Jan 13 - Jan 14
Total with taxes and fees
King Suite | Free Breakfast. Pool and Hot Tub
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 13 - Jan 14
Total with taxes and fees
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
9.8 out of 10, Exceptional, (47 reviews)
"Clean and close to everything."
United States
Anonymous traveler
$439 nightly
The price is $498
Jan 13 - Jan 14
Total with taxes and fees
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
$138 nightly
The price is $156
Jan 30 - Jan 31
Total with taxes and fees
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

Vacation Home in Downtown Madison

Studio Queen in the heart of downtown.
2.0 star property
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.
$193 nightly
The price is $223
Jan 13 - Jan 14
Total with taxes and fees
Studio Queen in the heart of downtown.
10.0 out of 10, Exceptional, (16 reviews)
"We had a great visit "
United States
Jennifer D.
$529 nightly
The price is $629
Jan 13 - Jan 14
Total with taxes and fees
Hot Tub - King Suite - Game Room - Large Groups

Apartment in Sun Prairie

1 Bedroom - 1220 Canterbury Ct
$251 nightly
The price is $282
Jan 13 - Jan 14
Total with taxes and fees
1 Bedroom - 1220 Canterbury Ct
9.8 out of 10, Exceptional, (37 reviews)
"The property itself was fantastic-clean and comfortable. The location was also very convenient in terms of access to downtown, the lake and so on. The neighborhood seemed to be a lot of college housing so there was some evening noise that quieted down by 10 or so. "
United States
Lily H.
$248 nightly
The price is $287
Jan 19 - Jan 20
Total with taxes and fees
Doty ★ Walk to Everything -Hotel Quality- Downtown
9.8 out of 10, Exceptional, (22 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.
$365 nightly
The price is $393
Jan 14 - Jan 15
Total with taxes and fees
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful spacious property, extremely clean and excellent host!"
United States
Jen F.
$508 nightly
The price is $572
Jan 13 - Jan 14
Total with taxes and fees
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
10.0 out of 10, Exceptional, (10 reviews)
"The house is great and the facilities in the house were well-functioning, and the dish washer saved us much time. The neighborhood is quiet and great views. We enjoyed our stay."
United States
Patti M.
$750 nightly
The price is $800
Jan 14 - Jan 15
Total with taxes and fees
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

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 $129 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.