Photo by Joel Holland

Windsor Vacation Rentals

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Vacation Rentals in Windsor

‘Happy’s Haven’ Cabin w/ Gas Grill & Fire Pit!
10.0 out of 10, Exceptional, (36)
"We had a great time! House was so clean and stocked with everything we needed. Would definitely stay again. Just adorable! I would recommend cutting the grass and storing your wood in a sheltered area. The wood was too wet to use-we had to purchase some & the grass was long with prickly vines on the stairs. The grass was long around the BBQ."
‘Happy’s Haven’ Cabin w/ Gas Grill & Fire Pit!
Barn House,5 Bedroom,Hot Tub,Ski/Golf,Beach Room,Indoor Slide,Tiki Bar,Pets Ok!
9.8 out of 10, Exceptional, (60)
"It was a perfect house for our group and we had a great weekend enjoying everything it had to offer!"
The price is CA $1,163
CA $1,838 total
includes taxes & fees
Jun 2 - Jun 3
Barn House,5 Bedroom,Hot Tub,Ski/Golf,Beach Room,Indoor Slide,Tiki Bar,Pets Ok!
Madison & ~UW~-Madison Area Lakefront Home
9.8 out of 10, Exceptional, (165)
"The cottage is clean and well stocked for a long weekend. The view of the lake is beautiful, and I'm sure it's even better in the warm months. We had everything we needed. Great little house for a long weekend."
Madison & ~UW~-Madison Area Lakefront Home
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Quietwater Cottage- On the Water, Scenic, Sandbars, Birds, Nature, Hot Tub!
9.8 out of 10, Exceptional, (221)
"Welcoming cozy cottage. Excellent location for bird watching & near by hiking at state parks. Friendly neighborhood :)"
Quietwater Cottage- On the Water, Scenic, Sandbars, Birds, Nature, Hot Tub!
Enjoy Nature with Full Comfort!
9.8 out of 10, Exceptional, (10)
"Space is clean, property is very pretty! Pool wasn’t ready for use, but can imagine it would add even more to the a summer stay! Owner is easy to communicate with. Ran into severe weather - owners were welcoming and ensured we were safe at all times. We will definitely be back to visit again!"
The price is CA $123
CA $188 total
includes taxes & fees
Jun 2 - Jun 3
Enjoy Nature with Full Comfort!
Amazing townhouse, amazing attractions, amazing city!
10.0 out of 10, Exceptional, (136)
"We rented this place to visit family in Madison and attend a ren faire. It was great as we were looking for a small place with a full kitchen to cook. Neat touches with the Alexa with song and light recommendations. We enjoyed the living room white board - played lots of Pictionary. Our group was myself, my daughter, and my sister. The basement den made a great third bedroom. I might recommend a pull out couch."
Amazing townhouse, amazing attractions, amazing city!
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
10.0 out of 10, Exceptional, (80)
"Everything was absolutely great! Location was perfect, lots of good restaurants and shopping near the house. Beautiful scenery and tranquil setting for relaxing. House was just as advertised and had everything we needed. Hosts are amazing and so kind! You’ll love the visits from their pups! Highly recommend!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Beautiful Cabin On The Scenic Wisconsin River/Lake Wisconsin
9.8 out of 10, Exceptional, (62)
"Nice little scenery and cabin. Hosts were very accommodating...couldn't ask for a better experience. Highly recommend if you're in that area. Will book again if life brings us out that way again."
Beautiful Cabin On The Scenic Wisconsin River/Lake Wisconsin
Near DT Madison - One Block from Lake Monona & Lake Loop Bike Path
10.0 out of 10, Exceptional, (18)
"Our stay at the Pink Acorn was amazing! Kelly truly makes her guests feel welcome. She left a sweet note and lovely treats. The house is stocked with everything you need and was exceptionally clean. The beds are super comfortable and have nice cozy blankets. Am added bonus was seeing rabbits and chipmunks in the backyard. Kelly leaves directions to walk to the beach around the corner and it’s a must do…and make sure to grab some ice cream at the shop across from the park."
Near DT Madison - One Block from Lake Monona & Lake Loop Bike Path
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
10.0 out of 10, Exceptional, (132)
"We loved our stay. The house was comfortable and clean. It had all the amenities. The location was spectacular, and the backyard was super peaceful. Joan was a great host and communication was easy. There are three bedrooms for six people and a full-size futon, which is great for our group of 6."
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard
A Pleasant Retreat- No Cleaning Fee & New Discounts
10.0 out of 10, Exceptional, (187)
"We loved this house and the gardens! It is ideally located, a quick walk into town. The Frank Lloyd Wright accents compliment the furnishings and decor of the house to a tee. It is well-stocked with everything you need! Connie and Randy (the owners) are delightful. We will definitely stay here again when the opportunity arises."
A Pleasant Retreat- No Cleaning Fee & New Discounts
Historic Home Near Wi Dells, Lake Wi & Skiing with Party Space!
9.0 out of 10, Wonderful, (7)
"There is more than enough beds for a group of 10 to have their own beds. The town is nice and quiet and it’s a 30 second walk to the nearest bar. We never felt on top of each other and were really comfortable in the house. I would go back!"
Historic Home Near Wi Dells, Lake Wi & Skiing with Party Space!
Waterfront w/ HOT TUB + King Suite + Game Room
9.2 out of 10, Wonderful, (15)
"St pattys fun with friends and family"
The price is CA $861
CA $1,734 total
includes taxes & fees
Jun 9 - Jun 10
Waterfront w/ HOT TUB + King Suite + Game Room
Spacious Home + Fire Pit, Waterfall, Hot Tub, Home Theater! 20 min to DT Madison
10.0 out of 10, Exceptional, (13)
"We stayed the weekend to watch our son play baseball against University of Wisconsin. Go Illini!! We also celebrated his 21st birthday with 3 other families. The house was clean and had plenty of space for everyone to sleep comfortably. We would definitely rent this house again."
Spacious Home + Fire Pit, Waterfall, Hot Tub, Home Theater! 20 min to DT Madison
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
10.0 out of 10, Exceptional, (13)
"We loved our visit to Madison, made even more special with our stay in this awesome retro house! All of the special touches throughout the house were amazing, we would definitely stay here again in the future."
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
10.0 out of 10, Exceptional, (18)
"Everything about our stay was fantastic! The house was nicely decorated and extremely clean. The kitchen was well appointed and had everything we needed. Beds were comfy. Shower was great. A perfect place for our group of friends to spend a long weekend. I wouldn’t hesitate to stay here again!"
The price is CA $368
CA $741 total
includes taxes & fees
Jun 24 - Jun 25
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Island View Hideaway - On the Water, Scenic, Sandbars, Birds, Nature, Hot Tub!
9.8 out of 10, Exceptional, (183)
"Great house have everything you need with great view and beautiful wildlife"
Island View Hideaway - On the Water, Scenic, Sandbars, Birds, Nature, Hot Tub!
2 Bedroom - Main Street Sun Prairie WI
9.6 out of 10, Exceptional, (17)
"Overall awesome place. Chris stayed in contact the entire time but wasn’t overbearing. We enjoyed our stay."
The price is CA $144
CA $305 total
includes taxes & fees
Jun 11 - Jun 12
2 Bedroom - Main Street Sun Prairie WI
Waters Edge Private Cottage
7.4 out of 10, Good, (3)
"Won $500 pull tab this weekend. Would stay again."
The price is CA $257
CA $585 total
includes taxes & fees
Jun 2 - Jun 3
Waters Edge Private Cottage
Conveniently Located just off University Avenue on Madison's West Side
10.0 out of 10, Exceptional, (107)
"huge property lots of open outdoor area, lots of indoor space. Excellent host."
Conveniently Located just off University Avenue on Madison's West Side
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See all available properties in Windsor
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.

Windsor Vacation Rental Travel Info

Other types of properties in Windsor you may be interested in

Days Inn by Wyndham Madison NE/Windsor
2.0 star property
7.0 out of 10, Good, (762)
"Great Stay!"
The price is CA $92
CA $97 total
includes taxes & fees
Jun 2 - Jun 3
Days Inn by Wyndham Madison NE/Windsor
The Madison Concourse Hotel and Governor's Club
3.5 star property
9.4 out of 10, Exceptional, (1644)
"Rooms are clean and updated. Wonderful view of the Capitol building. We walked to the Saturday am Farmers market. "
The price is CA $248
CA $286 total
includes taxes & fees
Jun 13 - Jun 14
The Madison Concourse Hotel and Governor's Club
Best Western Plus InnTowner Madison
3.0 star property
9.0 out of 10, Wonderful, (1003)
"Excellent room - very quiet. "
The price is CA $233
CA $269 total
includes taxes & fees
Jun 1 - Jun 2
Best Western Plus InnTowner 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.

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?

Barn House,5 Bedroom,Hot Tub,Ski/Golf,Beach Room,Indoor Slide,Tiki Bar,Pets Ok!: Visitors like this Windsor vacation home rental. It is located in the mountains and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a spa tub.

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 Barrymore Theatre.

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.

Recent reviews of Windsor properties
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