Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

Updated home with lake views, across the street from Lake Wisc!

Updated home with lake views, across the street from Lake Wisc!
Merrimac
10.0 out of 10, Exceptional, (34 reviews)
"Beautiful home, Merrimack is such a quaint town. "
United States
Laura L.
Updated home with lake views, across the street from Lake Wisc!

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
The price is ¥28,793
¥64,961 total
includes taxes & fees
Apr 21 - Apr 22
Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Enjoy Nature with Full Comfort!

Enjoy Nature with Full Comfort!
Verona
9.2 out of 10, Wonderful, (39 reviews)
"We were visiting friends in the area and it was a perfect spot to stay."
United States
Christine U.
The price is ¥14,278
¥21,758 total
includes taxes & fees
Apr 25 - Apr 26
Enjoy Nature with Full Comfort!

Cannery Square Unit - 106 by Patriot Properties

Cannery Square Unit - 106 by Patriot Properties
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 ¥21,416
¥53,008 total
includes taxes & fees
May 18 - May 19
Cannery Square Unit - 106 by Patriot Properties

2 Bedroom - Main Street Sun Prairie WI

2 Bedroom - Main Street Sun Prairie WI
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 ¥30,618
¥64,074 total
includes taxes & fees
Apr 21 - Apr 22
2 Bedroom - Main Street Sun Prairie WI

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 ¥20,623
¥27,394 total
includes taxes & fees
May 17 - May 18
King Suite | Free Breakfast. Pool and Hot Tub

Cannery Square Short Term Rentals -104 by Patriot

Cannery Square Short Term Rentals -104 by Patriot
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 ¥21,416
¥53,008 total
includes taxes & fees
May 18 - May 19
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 ¥23,561
¥30,586 total
includes taxes & fees
May 17 - May 18
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

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 ¥52,351
¥90,306 total
includes taxes & fees
Apr 21 - Apr 22
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is ¥22,051
¥28,519 total
includes taxes & fees
Apr 21 - Apr 22
Pool with Slide. Great for Business Travelers!

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 ¥39,343
¥80,669 total
includes taxes & fees
Apr 27 - Apr 28
Waters Edge Cottage

The Dylin

The Dylin
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (135 reviews)
"Well-decorated, coffee/kitchenette setup was great! "
United States
Chandra
The price is ¥19,622
¥22,663 total
includes taxes & fees
Apr 22 - Apr 23
The Dylin

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)
"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 ¥21,274
¥36,657 total
includes taxes & fees
Apr 26 - Apr 27
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

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, (51 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 ¥37,864
¥79,886 total
includes taxes & fees
Apr 22 - Apr 23
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Spring Escape Near UW

Spring Escape Near UW
Fitchburg
10.0 out of 10, Exceptional, (22 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 ¥52,085
¥128,621 total
includes taxes & fees
Apr 21 - Apr 22
Spring Escape Near UW

Cozy Cabin on Crooked Lane close to Lake Wisconsin

Cozy Cabin on Crooked Lane close to Lake Wisconsin
Poynette
10.0 out of 10, Exceptional, (1 review)
"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 ¥24,272
¥43,515 total
includes taxes & fees
May 4 - May 5
Cozy Cabin on Crooked Lane close to Lake Wisconsin

Cannery Square Short Term Rentals -307 by Patriot

Cannery Square Short Term Rentals -307 by Patriot
Sun Prairie
The price is ¥15,705
¥37,232 total
includes taxes & fees
Apr 26 - Apr 27
Cannery Square Short Term Rentals -307 by Patriot

1 Bedroom - 1220 Canterbury Ct

1 Bedroom - 1220 Canterbury Ct
Sun Prairie
The price is ¥23,320
¥45,155 total
includes taxes & fees
Apr 21 - Apr 22
1 Bedroom - 1220 Canterbury Ct

Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (40 reviews)
"Wonderful host, and a beautiful home within walking distance to many restaurants and museums. Parking nearby was easy to find. We were able to rest and relax, and make many meals there. Great kitchen amenities, and very comfortable beds. Truly a warm and inviting home. I would highly recommend!"
United States
Jacquie T.
The price is ¥26,985
¥45,460 total
includes taxes & fees
Apr 21 - Apr 22
Doty ★ Walk to Everything -Hotel Quality- Downtown

Capital City- 6 Miles from Madison with fireplace

Capital City- 6 Miles from Madison with fireplace
Sun Prairie
9.8 out of 10, Exceptional, (40 reviews)
"Absolutely would stay here again. Tami the host was wonderful, and very responsive. "
United States
Erika O.
The price is ¥59,490
¥99,766 total
includes taxes & fees
Apr 21 - Apr 22
Capital City- 6 Miles from Madison with 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

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

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Look no further and take a look at our great range of rental properties in Windsor!

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?

Private Pool - Hot Tub - Game Room - 20 min DT: Visitors like this Windsor vacation home rental. It offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.