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.
The price is CA $174
CA $442 total
includes taxes & fees
May 17 - May 18
Cannery Square Short Term Rentals

Cannery Square Short Term Rentals

Cannery Square Short Term Rentals
Sun Prairie
The price is CA $135
CA $319 total
includes taxes & fees
May 12 - May 13
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.
The price is CA $264
CA $557 total
includes taxes & fees
May 12 - May 13
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.
The price is CA $183
CA $316 total
includes taxes & fees
May 12 - May 13
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.
The price is CA $178
CA $236 total
includes taxes & fees
May 17 - May 18
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.
The price is CA $122
CA $186 total
includes taxes & fees
May 25 - May 26
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
The price is CA $203
CA $261 total
includes taxes & fees
May 14 - May 15
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.
The price is CA $339
CA $697 total
includes taxes & fees
May 12 - May 13
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.
The price is CA $217
CA $385 total
includes taxes & fees
May 13 - May 14
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 traveller
The price is CA $293
CA $612 total
includes taxes & fees
May 12 - May 13
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.
The price is CA $174
CA $442 total
includes taxes & fees
May 12 - May 13
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.
The price is CA $201
CA $389 total
includes taxes & fees
May 12 - May 13
1 Bedroom Apartment at Canterbury Court

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is CA $190
CA $246 total
includes taxes & fees
May 14 - May 15
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.
The price is CA $210
CA $642 total
includes taxes & fees
May 12 - May 13
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
The price is CA $159
CA $379 total
includes taxes & fees
May 12 - May 13
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
The price is CA $326
CA $687 total
includes taxes & fees
May 12 - May 13
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, (140 reviews)
"Small apartment for the price of a regular hotel room! Great decor 😎"
United States
jonathan
The price is CA $168
CA $194 total
includes taxes & fees
May 26 - May 27
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.
The price is CA $451
CA $788 total
includes taxes & fees
May 12 - May 13
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.
The price is CA $516
CA $1,195 total
includes taxes & fees
May 12 - May 13
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.
The price is CA $286
CA $376 total
includes taxes & fees
May 17 - May 18
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

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?

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.