Photo by Joel Holland

Windsor Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
28 Oct - 29 Oct
Tomorrow
29 Oct - 30 Oct
This weekend
31 Oct - 2 Nov
Next weekend
7 Nov - 9 Nov

Holiday Rentals in Windsor

Interior entrance
The Dylin by Mint House
The Dylin by Mint House
4.0 star property
9.2 out of 10, Wonderful, (105)
"Great location and very comfortable stay. Love the extra space to hang out."
United States
Brian
The Dylin by Mint House
Exterior
Lake Wisconsin Resort
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!"
United States
Shelley
Lake Wisconsin Resort
Outdoor spa tub
Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!
Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!
9.8 out of 10, Exceptional, (249)
"This was a nice place to stay that was away from hustle of the city. It was beautiful outside and the cabin was cute and cozy."
United States
Pauley A.
Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!
Interior
Historic Home Near Wi Dells, Lake Wi & Party Space Avail!
Historic Home Near Wi Dells, Lake Wi & Party Space Avail!
8.2 out of 10, Very good, (23)
"Plenty of sleeping options for kids.Close to Devils Head.Many restaurants within a short drive."
United States
Wesley R.
Historic Home Near Wi Dells, Lake Wi & Party Space Avail!
Terrace/patio
Private Pool - HOT TUB - Sauna - Game Room - Pets
Private Pool - HOT TUB - Sauna - Game Room - Pets
10.0 out of 10, Exceptional, (5)
"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...
United States
Patricia M.
The price is HK$3,029
HK$7,796 total
includes taxes & fees
30 Oct - 31 Oct
Private Pool - HOT TUB - Sauna - Game Room - Pets
Smart TV, music library, stereo
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!
10.0 out of 10, Exceptional, (100)
"Super communicative host, beautiful cabin "
United States
Jennifer
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!
Fridge, microwave, oven, stovetop
Doty ★ Walk to Everything -Hotel Quality- Downtown
Doty ★ Walk to Everything -Hotel Quality- Downtown
9.8 out of 10, Exceptional, (35)
"Beautiful apartment with all we needed for a comfortable family July 4th weekend away!! "
United States
Mindi Z.
The price is HK$2,908
HK$4,355 total
includes taxes & fees
2 Nov - 3 Nov
Doty ★ Walk to Everything -Hotel Quality- Downtown
Interior
Capital PrimeTime - 6 Miles from Madison w/ fireplace
Capital PrimeTime - 6 Miles from Madison w/ fireplace
9.8 out of 10, Exceptional, (29)
"Very, very nice, neat, and comfortable! Enjoyed our stay!"
United States
Mark P.
The price is HK$2,913
HK$4,876 total
includes taxes & fees
30 Oct - 31 Oct
Capital PrimeTime - 6 Miles from Madison w/ fireplace
Lobby
Pool with Slide. Great for Business Travelers!
Pool with Slide. Great for Business Travelers!
The price is HK$986
HK$1,289 total
includes taxes & fees
9 Nov - 10 Nov
Pool with Slide. Great for Business Travelers!
Terrace/patio
Free Breakfast Pool & Hot Tub. Near UW-Madison
Free Breakfast Pool & Hot Tub. Near UW-Madison
10.0 out of 10, Exceptional, (1)
"It was comfortable and clean and the staff was so nice. It was well located and the pool and hot tub were lovely as well."
United States
Joy E.
The price is HK$1,850
HK$2,452 total
includes taxes & fees
16 Nov - 17 Nov
Free Breakfast Pool & Hot Tub. Near UW-Madison
Outdoor spa tub
Island View Hideaway-Peaceful, On Water, Canoe, Scenic, Birds, Nature, Sandbars!
Island View Hideaway-Peaceful, On Water, Canoe, Scenic, Birds, Nature, Sandbars!
9.8 out of 10, Exceptional, (210)
"Wonderful cottage with everything we needed for a great stay. Loved watching the hummingbirds."
United States
Scott B.
Island View Hideaway-Peaceful, On Water, Canoe, Scenic, Birds, Nature, Sandbars!
Property grounds
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
10.0 out of 10, Exceptional, (118)
"Scenic property, super zen, lovely hosts!"
United States
Christina C.
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Exterior
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
9.8 out of 10, Exceptional, (46)
"Such a nice house! Great location and excellent amenities!"
United States
Carson M.
The price is HK$1,854
HK$3,867 total
includes taxes & fees
30 Oct - 31 Oct
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Smart TV, books
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
9.8 out of 10, Exceptional, (19)
"Enjoyed a wonderful stay."
United States
Michael D.
The price is HK$1,224
HK$2,913 total
includes taxes & fees
12 Nov - 13 Nov
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Exterior
ONE OF A KIND vacation rental with a view
ONE OF A KIND vacation rental with a view
10.0 out of 10, Exceptional, (145)
"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. "
United States
Deborah C.
ONE OF A KIND vacation rental with a view
Outdoor dining
Lake Monona Waterfront + HOT TUB + Game Room
Lake Monona Waterfront + HOT TUB + Game Room
9.6 out of 10, Exceptional, (32)
"Great property!"
United States
Steve V.
Lake Monona Waterfront + HOT TUB + Game Room
Terrace/patio
King Suite | Free Breakfast. Pool and Hot Tub
King Suite | Free Breakfast. Pool and Hot Tub
8.6 out of 10, Excellent, (4)
"Great place for a stay."
United States
Andy D.
The price is HK$840
HK$1,139 total
includes taxes & fees
23 Nov - 24 Nov
King Suite | Free Breakfast. Pool and Hot Tub
Outdoor pool, a heated pool
Contemporary home in quiet neighborhood with pool & great back yard close to all
Contemporary home in quiet neighborhood with pool & great back yard close to all
9.6 out of 10, Exceptional, (10)
"Everything was just as advertised. The backyard & stay was very enjoyable. Thank you for a lovely stay, Sheila!"
United States
kelly p.
Contemporary home in quiet neighborhood with pool & great back yard close to all
Smart TV, fireplace, DVD player, books
Conveniently Located just off University Avenue on Madison's West Side
Conveniently Located just off University Avenue on Madison's West Side
10.0 out of 10, Exceptional, (131)
"House is spacious and situated on a huge lot. Perfect for our family reunion. Lots of welcoming touches in the home."
United States
Elizabeth F.
Conveniently Located just off University Avenue on Madison's West Side
Interior
Exceptional 4 Bed 3 Bath Hot tub next to woods -Comfortable! - 21 min to Madison
Exceptional 4 Bed 3 Bath Hot tub next to woods -Comfortable! - 21 min to Madison
10.0 out of 10, Exceptional, (132)
"Wonderful host who checked with us the first day to see if we were comfortable. Spotless home with all high end appliances. Spacious and comfortable. The screened in porch was used every day. "
United States
Jenni P.
Exceptional 4 Bed 3 Bath Hot tub 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

Hilton Garden Inn Madison Downtown

Hilton Garden Inn Madison Downtown

10/10 Excellent
"Very friendly staff. Great location for UW events. "
Susan 2-night trip
Posted 9 hours ago
Hilton Garden Inn Madison Downtown

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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?

COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!: This holiday home rental outside of Windsor is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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.