Photo by Joel Holland

Windsor Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Windsor

The Dylin by Mint House

4.0 star property
9.2 out of 10, Wonderful, (83)
"Nice, clean, well-equipped and well-decorated rooms. "
The Dylin by Mint House

Lake Wisconsin Resort

3.0 star property
10.0 out of 10, Exceptional, (1)
"The cabins looked small from the outside, but we're actually very spacious we didn't feel cramped everything was very clean there was a full kitchen a table big enough to sit at least four. I think the only thing that wasn't 100% perfect was the beds are a little small they were stiff and the pillows were also very small and serviceable. I would still definitely stay there again 100% and would recommend it to everyone!"
Lake Wisconsin Resort

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

9.8 out of 10, Exceptional, (243)
"The place is fully stocked and very clean. There was everything we needed and more. Host is amazing. The post talks about the beach down the road...don't bother, the beach in yard is perfect for pets or small children. Thank you for a great experience on our short time there. "
Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!

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

10.0 out of 10, Exceptional, (91)
"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 !!

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

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (141)
"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

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

9.8 out of 10, Exceptional, (87)
"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!

Capital PrimeTime - 6 Miles from Madison w/ fireplace

10.0 out of 10, Exceptional, (25)
"Would recommend - very good location, nice space, and great host!"
The price is AU$992
includes taxes & fees
24 Aug - 25 Aug
Capital PrimeTime - 6 Miles from Madison w/ fireplace

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

10.0 out of 10, Exceptional, (1)
"The Sun Prairie house perfectly met the goals for our family gathering of six adults and golden retriever for social and private space and so many entertainment options! The house was spotless, the neighborhood quiet, with Woodmans close by for shopping. We had 5 days of sunshine, golfing nearby courses, enjoying afternoon pool time, evening hot tub, and bug-free outdoor dining-so private and relaxing! We never ran out of room for food/drinks in the large volume fridge (loved the beverage...
The price is AU$2,068
includes taxes & fees
20 Aug - 21 Aug
Private Pool - HOT TUB - Sauna - Game Room - Pets

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

2.0 star property
10.0 out of 10, Exceptional, (23)
"Super clean, well lit, and beautiful view! Would definitely stay again."
The price is AU$554
includes taxes & fees
1 Sept - 2 Sept
One Bedroom King with Den with views of the heart of downtown.

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

8.4 out of 10, Very good, (18)
"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!

Waterfront Lodi Vacation Rental on Lake Wisconsin!

10.0 out of 10, Exceptional, (14)
"Very clean! Awesome accommodations! Perfect couple of nights on the lake - kids even jumped in in early May! Washer/dryer is always an added bonus. Coffee bar a nice touch, and the kids loved the lanterns : )"
Waterfront Lodi Vacation Rental on Lake Wisconsin!

Paoli Den - Newly Remodeled!

9.8 out of 10, Exceptional, (23)
"Prefect"
Paoli Den - Newly Remodeled!

Escape to tranquility – your countryside haven, and at times with a horse or two

Escape to tranquility – your countryside haven, and at times with a horse or two

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

Madison & ~UW~-Madison Area Lakefront Home

10.0 out of 10, Exceptional, (194)
"The cottage is a great location, hiking trail, restaurants and pubs in walking distance, and short drive to Madison. It is well-furnished, comfortable and is located on the water with great views. My friends and I would highly recommend this property."
Madison & ~UW~-Madison Area Lakefront Home

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

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

10.0 out of 10, Exceptional, (3)
"Great place to land for a weekend in Madison."
The price is AU$532
includes taxes & fees
24 Aug - 25 Aug
One Bedroom King/accessible with views of Lake Monona in the heart of downtown.

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

9.8 out of 10, Exceptional, (73)
"Hosts were gracious and attentive. Viewing wildlife on the river from the living room windows was fascinating.Comfortable beds.Nearby restaurant had great food."
Beautiful Cabin on Scenic WI River/Lake Wisconsin. Close to WI Dells and Madison

Enjoy Nature with Full Comfort!

9.4 out of 10, Exceptional, (29)
"Great location, beautiful, clean, and friendly host"
The price is AU$200
includes taxes & fees
21 Aug - 22 Aug
Enjoy Nature with Full Comfort!
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

One Bedroom King with Den with views of Lake Monona in the heart of downtown.: This holiday home rental outside of Windsor is in the city centre and offers cable TV to help you feel perfectly comfortable in your new surroundings.

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.