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Windsor Holiday Rentals

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Holiday Rentals in Windsor

The Dylin

4.0 star property
9.2 out of 10, Wonderful, (78)
"Very comfortable and convenient. Would be happy to stay there again."
The Dylin

Relax in this clean cozy 3 bedroom, 2 bath home in the heart of Madison. Perfect

2.0 out of 10, (2)
"Host never showed up to let us in the property and still has not reimbursed me "
Relax in this clean cozy 3 bedroom, 2 bath home in the heart of Madison. Perfect

Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!

9.8 out of 10, Exceptional, (240)
"Cozy cabin, nestled in the outskirts of Baraboo. Great for the scenery and hiking. A chance to unplug and get away from the big city to spend quality time nature. "
Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!

Two bedroom suite with city views in the heart of downtown Madison

9.8 out of 10, Exceptional, (29)
"Perfect for a weekend in Madison. A good location close to everything. "
The price is AU$709
includes taxes & fees
27 July - 28 July
Two bedroom suite with city views in the heart of downtown Madison

One Bedroom King with Den with views of Lake Monona in the heart of downtown.

9.4 out of 10, Exceptional, (22)
"The property was beautiful, safe, and in a perfect location for the event we were attending!"
The price is AU$606
includes taxes & fees
30 July - 31 July
One Bedroom King with Den with views of Lake Monona in the heart of downtown.

Private Pool - HOT TUB - Sauna - Game Room - Pets

Private Pool - HOT TUB - Sauna - Game Room - Pets

One Bedroom King with Den with views of the heart of downtown.

2.0 star property
9.6 out of 10, Exceptional, (20)
"Great stay, easy location."
The price is AU$584
includes taxes & fees
27 July - 28 July
One Bedroom King with Den with views of the heart of downtown.

Amazing Lake Wisconsin Views!!! Newly Remodeled Cottage with Modern Amenities!

9.8 out of 10, Exceptional, (86)
"This was a great place to stay for a weekend getaway with some friends. Would love to come by again in the summer time "
Amazing Lake Wisconsin Views!!! Newly Remodeled Cottage with Modern Amenities!

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

9.8 out of 10, Exceptional, (73)
"A top-notch experience. Beautiful views, completely stocked with everything you need to cook a breakfast or a dinner. Loved the whole week there. "
Beautiful Cabin on Scenic WI River/Lake Wisconsin. Close to WI Dells and Madison

COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!

10.0 out of 10, Exceptional, (87)
"Such a charming spot right on the lake! Direct access to the water, beautiful views, close to a bunch of fun bars and restaurants, and an easy drive to Devil’s Lake, Wisconsin Dells, and Madison. We stayed for a long weekend with our six month old, and it was great! Joe, the owner, is so friendly and responsive. Highly recommended!"
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!

Capital PrimeTime - 6 Miles from Madison w/ fireplace

10.0 out of 10, Exceptional, (24)
"Would recommend - very good location, nice space, and great host!"
The price is AU$973
includes taxes & fees
27 July - 28 July
Capital PrimeTime - 6 Miles from Madison w/ fireplace

Doty ★ Walk to Everything -Hotel Quality- Downtown

9.8 out of 10, Exceptional, (33)
"Had a great stay!"
Doty ★ Walk to Everything -Hotel Quality- Downtown

Studio queen with views of Lake Monona in the heart of downtown Madison

9.4 out of 10, Exceptional, (8)
"The property location is great, walking distance to great restaurants, the Farmers market, and close to walking/running trails. "
The price is AU$464
includes taxes & fees
27 July - 28 July
Studio queen with views of Lake Monona in the heart of downtown Madison

Conveniently Located just off University Avenue on Madison's West Side

10.0 out of 10, Exceptional, (124)
"Very spacious, well appointed house in a quiet neighborhood, convenient to Madison."
Conveniently Located just off University Avenue on Madison's West Side

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (139)
"This is our second stay and will gladly come back. It is easy to maneuver around Madison and the house is a spectacular vintage 80’s home. "
ONE OF A KIND vacation rental with a view

Lakeview Cabin > Unique Mid-Century Tucked in Bluff

10.0 out of 10, Exceptional, (15)
"Beautiful view and rolling hills made for a relaxing stay."
The price is AU$702
includes taxes & fees
25 Aug - 26 Aug
Lakeview Cabin > Unique Mid-Century Tucked in Bluff

One Bedroom King with views of the heart of downtown.

2.0 star property
10.0 out of 10, Exceptional, (2)
"I loved the location and the area it was located. I really loved the view and the clearness of the place as well. It was very homey and cozy. "
The price is AU$548
includes taxes & fees
30 July - 31 July
One Bedroom King with views of the heart of downtown.

Enjoy Nature with Full Comfort!

9.6 out of 10, Exceptional, (28)
"Great location, beautiful, clean, and friendly host"
The price is AU$197
includes taxes & fees
27 July - 28 July
Enjoy Nature with Full Comfort!

Historic Home Near Wi Dells, Lake Wi & Party Space Avail!

8.6 out of 10, Excellent, (16)
"Plenty of sleeping options for kids.Close to Devils Head.Many restaurants within a short drive."
Historic Home Near Wi Dells, Lake Wi & Party Space Avail!

Exceptional 4 Bed 3 Bath next to woods -Comfortable! - 21 min to Madison

10.0 out of 10, Exceptional, (130)
"Clean, quiet neighborhood, and plenty of space for our whole crew during Ironman weekend. Would recommend for anyone visiting the Madison area. "
Exceptional 4 Bed 3 Bath next to woods -Comfortable! - 21 min to 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

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?

Two bedroom suite with city views in the heart of downtown Madison: This holiday home rental outside of Windsor is on a lake, and equipped with air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Warner Park and East Towne Mall.

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.