Photo by Joel Holland

Windsor Holiday Rentals

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Holiday Rentals in Windsor

Outdoor dining
‘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!
Fridge, microwave, oven, stovetop
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 NZ$2,193
per night
5 Jun - 6 Jun
Barn House,5 Bedroom,Hot Tub,Ski/Golf,Beach Room,Indoor Slide,Tiki Bar,Pets Ok!
On the beach
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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Lake
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!
Property grounds
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 NZ$218
per night
30 May - 31 May
Enjoy Nature with Full Comfort!
Fridge, microwave, oven, stovetop
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!
Property grounds
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
Property grounds
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
Property grounds
Near DT Madison - One Block from Lake Monona & Lake Loop Bike Path
10.0 out of 10, Exceptional, (17)
"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
Outdoor dining
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
Exterior
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
5 bedrooms, free WiFi, bed sheets
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!
Property grounds
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 NZ$2,207
per night
6 Jun - 7 Jun
Waterfront w/ HOT TUB + King Suite + Game Room
Property grounds
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
Marina
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
Exterior
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 NZ$878
per night
24 Jun - 25 Jun
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Pool
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!
TV
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 NZ$363
per night
30 May - 31 May
2 Bedroom - Main Street Sun Prairie WI
Property grounds
Waters Edge Private Cottage
7.4 out of 10, Good, (3)
"Won $500 pull tab this weekend. Would stay again."
The price is NZ$696
per night
30 May - 31 May
Waters Edge Private Cottage
Interior
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.

Other types of properties in Windsor you may be interested in

Exterior
Days Inn by Wyndham Madison NE/Windsor
2.0 star property
7.0 out of 10, Good, (762)
"Great Stay!"
The price is NZ$115
per night
5 Jun - 6 Jun
Days Inn by Wyndham Madison NE/Windsor
Exterior
The Madison Concourse Hotel and Governor's Club
3.5 star property
9.4 out of 10, Exceptional, (1639)
"We loved the Governor's lounge, it was nice to sit with a view of the capital building! Staff and service was excellent as well."
The price is NZ$411
per night
31 May - 1 Jun
The Madison Concourse Hotel and Governor's Club
Exterior
Best Western Plus InnTowner Madison
3.0 star property
9.0 out of 10, Wonderful, (1002)
"Great breakfast and nice room. "
The price is NZ$287
per night
9 Jun - 10 Jun
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Windsor holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Windsor. 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 Windsor. 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 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 holiday 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 Windsor short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals in Windsor close to Mousehouse Cheesehaus, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 are some of the best holiday rentals that Windsor has to offer?

Barn House,5 Bedroom,Hot Tub,Ski/Golf,Beach Room,Indoor Slide,Tiki Bar,Pets Ok!: This holiday home rental outside of Windsor is located in the mountains, and has a patio, a garden and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot 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 wider area, you’ll find East Towne Mall and Barrymore Theatre.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a family getaway.

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