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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
13 Jul - 14 Jul
Tomorrow
14 Jul - 15 Jul
Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul

Holiday Rentals in Windsor

The Dylin
Interior entrance

The Dylin

4.0 star property
9.2 out of 10, Wonderful, (75)
"Very comfortable and convenient. Would be happy to stay there again."
The Dylin
One Bedroom King with Den with views of Lake Monona in the heart of downtown.
Exterior

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

9.6 out of 10, Exceptional, (20)
"What a great spot right on the lake and near a lot of great restaurants and places. "
The price is HK$2,347
HK$3,092 total
includes taxes & fees
20 Jul - 21 Jul
One Bedroom King with Den with views of Lake Monona in the heart of downtown.
Two bedroom suite with city views in the heart of downtown Madison
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (29)
"Supper clean, comfortable beds and great location. Will definitely stay here again. "
The price is HK$2,740
HK$3,618 total
includes taxes & fees
14 Jul - 15 Jul
Two bedroom suite with city views in the heart of downtown Madison
Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!
Outdoor spa tub

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

9.8 out of 10, Exceptional, (239)
"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!
Beautiful Cabin on Scenic WI River/Lake Wisconsin. Close to WI Dells and Madison
Exterior

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
Doty ★ Walk to Everything -Hotel Quality- Downtown
Fridge, microwave, oven, stovetop

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
Exterior

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

9.4 out of 10, Exceptional, (8)
"We had no issues with our stay and really enjoyed the unit we booked. "
The price is HK$1,484
HK$1,958 total
includes taxes & fees
16 Jul - 17 Jul
Studio queen with views of Lake Monona in the heart of downtown Madison
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Fridge, microwave, oven, stovetop

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 HK$1,866
HK$3,707 total
includes taxes & fees
16 Jul - 17 Jul
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Capital PrimeTime - 6 Miles from Madison w/ fireplace
Exterior

Capital PrimeTime - 6 Miles from Madison w/ fireplace

10.0 out of 10, Exceptional, (22)
"Would recommend - very good location, nice space, and great host!"
The price is HK$2,944
HK$4,963 total
includes taxes & fees
14 Jul - 15 Jul
Capital PrimeTime - 6 Miles from Madison w/ fireplace
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!
Smart TV, music library, stereo

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

10.0 out of 10, Exceptional, (85)
"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 !!
Escape to tranquility – your countryside haven, and at times with a horse or two
Outdoor dining

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

The price is HK$1,256
HK$2,073 total
includes taxes & fees
25 Jul - 26 Jul
Escape to tranquility – your countryside haven, and at times with a horse or two
Enjoy Nature with Full Comfort!
Outdoor dining

Enjoy Nature with Full Comfort!

9.6 out of 10, Exceptional, (27)
"Great location, beautiful, clean, and friendly host"
The price is HK$636
HK$1,002 total
includes taxes & fees
15 Jul - 16 Jul
Enjoy Nature with Full Comfort!
Amazing Lake Wisconsin Views!!! Newly Remodeled Cottage with Modern Amenities!
Outdoor dining

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

9.8 out of 10, Exceptional, (85)
"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!
Conveniently Located just off University Avenue on Madison's West Side
Smart TV, fireplace, DVD player, books

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

10.0 out of 10, Exceptional, (123)
"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
Exterior

ONE OF A KIND vacation rental with a view

10.0 out of 10, Exceptional, (138)
"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
Madison & ~UW~-Madison Area Lakefront Home
Fridge, microwave, oven, stovetop

Madison & ~UW~-Madison Area Lakefront Home

10.0 out of 10, Exceptional, (192)
"Enjoyed the stay — great access to nature and got a beautiful sunset!!"
Madison & ~UW~-Madison Area Lakefront Home
Historic Home Near Wi Dells, Lake Wi & Party Space Avail!
Interior

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
Exterior

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

10.0 out of 10, Exceptional, (128)
"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
Two Bedroom with views of Lake Monona in the heart of downtown Madison
Interior

Two Bedroom with views of Lake Monona in the heart of downtown Madison

10.0 out of 10, Exceptional, (5)
"We loved everything about this property. Would definitely stay there again."
The price is HK$2,897
HK$3,826 total
includes taxes & fees
17 Jul - 18 Jul
Two Bedroom with views of Lake Monona in the heart of downtown Madison
Island View Hideaway-Peaceful, On Water, Canoe, Scenic, Birds, Nature, Sandbars!
Outdoor spa tub

Island View Hideaway-Peaceful, On Water, Canoe, Scenic, Birds, Nature, Sandbars!

9.8 out of 10, Exceptional, (204)
"Very clean nice place with a wonderful hot tub, and amazing views."
Island View Hideaway-Peaceful, On Water, Canoe, Scenic, Birds, Nature, Sandbars!
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
Sign in
Sign up, it's free

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?

Relax in this clean cozy 3 bedroom, 2 bath home in the heart of Madison. Perfect: This holiday home rental outside of Windsor is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a stovetop and a microwave.

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.