Photo by Joel Holland

Windsor Holiday Rentals

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Holiday Rentals in Windsor

A Pleasant Retreat- No Cleaning Fee & New Discounts

10.0 out of 10, Exceptional, (221)
"We stayed two nights on a weekend to celebrate with family and our college graduate. We had 7 stay comfortably using the sunroom bed. The house was amazing and had everything we needed throughout the weekend. The backyard is very nice. We really loved everything about the house. The hosts were excellent, very helpful and extremely easy to communicate with. The neighborhood is very quiet and the location gives easy access to Madison. An amazing weekend! We would highly recommend!"
The price is AU$469
includes taxes & fees
5 Jan - 6 Jan
A Pleasant Retreat- No Cleaning Fee & New Discounts

‘Happy’s Haven’ Cabin w/ Gas Grill & Fire Pit!

10.0 out of 10, Exceptional, (45)
"You could not imagine a more perfect location to stay. The privacy, views of the lake and the well appointed home were all provided the perfect makings for a glorious vacation. "
‘Happy’s Haven’ Cabin w/ Gas Grill & Fire Pit!

Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

10.0 out of 10, Exceptional, (100)
"Exquisitely laid out and decorated to blend perfectly with nature’s beauty. Attention to detail and wonderful amenities. You will not be disappointed with this cozy private retreat!"
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

9.8 out of 10, Exceptional, (31)
"Jake’s place was perfect for our stay, as it was a relaxing, clean and a nice home. The two floor layout worked especially well for our infant daughter so she had a quiet place to sleep, while we could cook and hang out in the living room. The only suggestion to the host is to install curtains along the picturesque sliding doors for a bit of extra privacy at nighttime."
The price is AU$857
includes taxes & fees
15 Jan - 16 Jan
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Quietwater Cottage- On the Water, Scenic, Sandbars, Birds, Nature, Hot Tub!

9.8 out of 10, Exceptional, (232)
"Great place. Going back soon"
Quietwater Cottage- On the Water, Scenic, Sandbars, Birds, Nature, Hot Tub!

Amazing townhouse, amazing attractions, amazing city!

10.0 out of 10, Exceptional, (159)
"Relaxing four getaway night stay with a dear friend. Location is perfect and close to top notch restaurants, grocery stores, and downtown Madison. Quiet neighborhood. Timely, friendly communication with owners. Comfortable beds. The unit is clean, stylish, comfortable and we loved our stay! "
Amazing townhouse, amazing attractions, amazing city!

Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path

10.0 out of 10, Exceptional, (26)
"We were celebrating our son's graduation. This was a perfect spot and couldn't be happier with our selection. We will definitely stay here again if the need arises. "
Near DT Madison - Half Block from Lake Monona & 1 Block from Lake Loop Bike Path

Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard

10.0 out of 10, Exceptional, (144)
"We have stayed multiple times, and always enjoy the country setting; cleanliness; well equipped, large kitchen; nearby dog park; and wonderful hosts. "
Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard

Spacious country retreat w/pool 10 minutes to downtown Madison! Pet friendly!

8.0 out of 10, Very good, (7)
"Lovely property and spacious home with lots of good hangout areas. Fully stocked with anything u could need and nice decorations throughout"
Spacious country retreat w/pool 10 minutes to downtown Madison! Pet friendly!

Doty ★ Walk to Everything -Hotel Quality- Downtown

9.8 out of 10, Exceptional, (30)
"Had a wonderful first trip to Madison for the entire week of Thanksgiving. The house was absolutely perfect. Clean, cute, warm, perfect location to everything downtown. Also had better quality amenities than a lot of rentals; nice towels, comfortable beds and bedding and great furniture, fully stocked kitchen utensils and things. Felt perfectly at home. "
Doty ★ Walk to Everything -Hotel Quality- Downtown

Enjoy Nature with Full Comfort!

9.8 out of 10, Exceptional, (23)
"The location was rural but very close to town. The room had a separate entrance and I felt very welcome even with my two dogs. It was a very cosy arrangement and there were a lot of thoughtful additions such as a clean bathrobe and (brand new) slippers. There was even an extra dog bed if I would have needed it. I really enjoyed my stay."
The price is AU$224
includes taxes & fees
5 Jan - 6 Jan
Enjoy Nature with Full Comfort!

Cozy 3 Bedroom Cottage- Breathtaking Lake Views

9.2 out of 10, Wonderful, (13)
"Great location. We enjoyed our stay and had many laughs. The bugs and bees in the kitchen along with the toaster and microwave that sometimes worked added to the funny memories. "
The price is AU$616
includes taxes & fees
6 Jan - 7 Jan
Cozy 3 Bedroom Cottage- Breathtaking Lake Views

Beautiful Cabin on Scenic WI River/Lake Wisconsin. Close to WI Dells and Madison

9.8 out of 10, Exceptional, (68)
"Nice, well equipped home, cushions on furniture need replacing but otherwise comfortable. Thanks for the opportunity to stay there!"
Beautiful Cabin on Scenic WI River/Lake Wisconsin. Close to WI Dells and Madison

Historic Home Near Wi Dells, Lake Wi & Skiing with Party Space!

8.8 out of 10, Excellent, (13)
"I loved the vibe of this house. So much character and nicely updated. We loved walking to the ferry, the ice cream stand, and taking a ride across the lake. It was the perfect stay for our weekend trip to Baraboo and Devil’s Lake. "
Historic Home Near Wi Dells, Lake Wi & Skiing with Party Space!

Wisconsin River Valley Farmhouse: Fire Pit & View

10.0 out of 10, Exceptional, (46)
"Great property, easy and easy out, loved that the dogs could be with us."
Wisconsin River Valley Farmhouse: Fire Pit & View

Home away from home!!!

8.6 out of 10, Excellent, (11)
"This is a basement apartment in a gorgeous neighborhood. Took us about 25 minutes to get into the campus area, which we came to see. Great WiFi, we worked during tne day, house was quiet. Comfortable bed, sofa couch, and large bathroom. It was cool but there are portable heaters that were perfect. Close to a grocery store. Also, Gus’s Diner was minutes away and had very nice food. Great pizza close by too. House is next to an open space, saw cranes and goldfinches. Great place to stay. Hosts...
Home away from home!!!

Updated home with lake views-near skiing, Devil's Lake, and 30 min to WI Dells!

10.0 out of 10, Exceptional, (26)
"Perfect home base for a two-family vacay. Four teenage boys and two moms and we never felt crowded. Easy drive to the Dells, Devil’s Lake, and Baraboo. Beautiful views of Lake WI from the deck and a quick walk to fishing at Memorial park and ice cream at the ferry crossing. The house was very clean, stocked with basics, and communication with the owner was so easy. Highly recommend!"
Updated home with lake views-near skiing, Devil's Lake, and 30 min to WI Dells!

10min to Capitol + Prime Location + Pets Welcome

9.8 out of 10, Exceptional, (18)
"Cute house was nice and clean."
10min to Capitol + Prime Location + Pets Welcome

Madison & ~UW~-Madison Area Lakefront Home

10.0 out of 10, Exceptional, (183)
"The lake cottage was absolutely beautiful!! The home was very clean and organized and not to mention the amazing views!! The host was great at responding to any questions we had too. We will definitely be back! "
Madison & ~UW~-Madison Area Lakefront Home

Lake Monona Waterfront + HOT TUB + Game Room

9.6 out of 10, Exceptional, (27)
"Excellent location with beautiful view of the canal. Kids enjoyed watching the ducks and squirrels. Had everything we needed to enjoy our family quality time"
Lake Monona Waterfront + HOT TUB + Game Room
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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Other types of properties in Windsor you may be interested in

Days Inn by Wyndham Madison NE/Windsor

2.0 star property
7.2 out of 10, Good, (830)
"We stayed here for about a month while our RV was being repaired. It was clean, comfortable, and the staff was amazing! Everyone was really friendly and helpful. There's an excellent restaurant next door (Rodeside Grill) and it's close to Madison and DeForest."
The price is AU$104
includes taxes & fees
7 Jan - 8 Jan
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, (2216)
"Location was #1 very walkable around the capital for restaurants and bars, walk to the overture center for the ballet. Check-in was seamless. Lewis was the best! We enjoyed the bar, the most comfortable beds and pillows and the exquisite amenities, especially toiletry items. Definitely stay back here on our next trip to Madison in June"
The price is AU$259
includes taxes & fees
5 Jan - 6 Jan
The Madison Concourse Hotel and Governor's Club

DoubleTree by Hilton Madison East

4.0 star property
9.4 out of 10, Exceptional, (826)
"Everyone we came in contact with at the hotel was super friendly and helpful during our stay"
The price is AU$204
includes taxes & fees
6 Jan - 7 Jan
DoubleTree by Hilton Madison East
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.

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?

A Pleasant Retreat- No Cleaning Fee & New Discounts: This holiday home rental outside of Windsor offers a patio, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 wider area, you’ll find East Towne Mall and Madison Area Technical College.

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.