Windsor Holiday Rentals

  • 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

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Windsor holiday rentals

Exterior

Cannery Square Short Term Rentals -104 by Patriot

Cannery Square Short Term Rentals -104 by Patriot
Sun Prairie
9.6 out of 10, Exceptional, (48 reviews)
"This was our third or fourth year staying there while visiting family for the holidays. Comfy beds, great location!"
United States
Sara M.
The price is HK$1,017
HK$2,562 total
includes taxes & fees
29 Apr - 30 Apr
Cannery Square Short Term Rentals -104 by Patriot
Interior

Updated home with lake views, across the street from Lake Wisc!

Updated home with lake views, across the street from Lake Wisc!
Merrimac
10.0 out of 10, Exceptional, (34 reviews)
"Beautiful home, Merrimack is such a quaint town. "
United States
Laura L.
The price is HK$1,056
HK$2,218 total
includes taxes & fees
29 Apr - 30 Apr
Updated home with lake views, across the street from Lake Wisc!
Fridge, microwave, oven, stovetop

2 Bedroom - Main Street Sun Prairie WI

2 Bedroom - Main Street Sun Prairie WI
Sun Prairie
9.6 out of 10, Exceptional, (40 reviews)
"The host was very responsive and very kind and considerate to our reason for traveling. The property was beautiful and clean inside and out, we really enjoyed our stay."
United States
Sha'Vonne G.
The price is HK$1,510
HK$3,196 total
includes taxes & fees
29 Apr - 30 Apr
2 Bedroom - Main Street Sun Prairie WI
Terrace/patio

King Suite | Free Breakfast. Pool and Hot Tub

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.0 out of 10, Very good, (5 reviews)
"Great place for a stay."
United States
Andy D.
The price is HK$822
HK$1,127 total
includes taxes & fees
19 Apr - 20 Apr
King Suite | Free Breakfast. Pool and Hot Tub
Exterior

Cannery Square Unit - 106 by Patriot Properties

Cannery Square Unit - 106 by Patriot Properties
Sun Prairie
9.4 out of 10, Exceptional, (28 reviews)
"Cute little spot, easy to walk to surrounding business "
United States
Lisa V.
The price is HK$1,057
HK$2,617 total
includes taxes & fees
18 May - 19 May
Cannery Square Unit - 106 by Patriot Properties
Terrace/patio

Cozy Cabin on Crooked Lane close to Lake Wisconsin

Cozy Cabin on Crooked Lane close to Lake Wisconsin
Poynette
10.0 out of 10, Exceptional, (1 review)
"Pet friendly cabin in the woods. Mostly updated and nice for 4-6 people. We stayed with our dogs and it worked well for us. "
United States
Jon A.
The price is HK$1,198
HK$2,157 total
includes taxes & fees
4 May - 5 May
Cozy Cabin on Crooked Lane close to Lake Wisconsin
Interior

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Sun Prairie
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful spacious property, extremely clean and excellent host!"
United States
Jen F.
The price is HK$2,582
HK$4,525 total
includes taxes & fees
26 Apr - 27 Apr
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Smart TV, fireplace, stereo, printers

Spring Escape Near UW

Spring Escape Near UW
Fitchburg
10.0 out of 10, Exceptional, (21 reviews)
"We enjoyed staying here. VERY nice house, easy access, clean, a lot of space, no issues. We would book here again!"
United States
Liz A.
The price is HK$2,656
HK$6,464 total
includes taxes & fees
21 Apr - 22 Apr
Spring Escape Near UW
Dining

Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful house! We loved the basement game room and found our stay very comfortable. "
United States
Anonymous traveller
The price is HK$1,420
HK$3,204 total
includes taxes & fees
20 Apr - 21 Apr
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Lobby

King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
Fitchburg
The price is HK$1,151
HK$1,487 total
includes taxes & fees
17 May - 18 May
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
Outdoor dining

Enjoy Nature with Full Comfort!

Enjoy Nature with Full Comfort!
Verona
9.2 out of 10, Wonderful, (39 reviews)
"We were visiting friends in the area and it was a perfect spot to stay."
United States
Christine U.
The price is HK$704
HK$1,073 total
includes taxes & fees
6 May - 7 May
Enjoy Nature with Full Comfort!
Property grounds

Waters Edge Cottage

Waters Edge Cottage
Merrimac
7.8 out of 10, Good, (12 reviews)
"Won $500 pull tab this weekend. Would stay again."
United States
Ryan R.
The price is HK$1,941
HK$4,006 total
includes taxes & fees
24 Apr - 25 Apr
Waters Edge Cottage
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!
Monona
9.8 out of 10, Exceptional, (51 reviews)
"It was lovely to be by the lake and have the view from the living room along with gas fireplace. So relaxing even in the off season."
United States
Justine K.
The price is HK$1,869
HK$3,926 total
includes taxes & fees
19 Apr - 20 Apr
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Smart TV, computer monitors

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Middleton
10.0 out of 10, Exceptional, (2 reviews)
"This stay was truly perfect! Our hosts thought of every single detail and more. The property was perfectly appointed with all the little touches that made it ideal for a quiet couple's getaway just outside Madison. We drove nearly 8 hours north from Kansas City to get here, so imagine how wonderful it was to walk into a warm, cozy, welcoming house that had snacks on hand and a pizza delivery number front and center waiting for us! Best part of all - it was dog-friendly! Our dog immediately felt...
United States
Heather P.
The price is HK$1,049
HK$1,817 total
includes taxes & fees
26 Apr - 27 Apr
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Reception

The Dylin

The Dylin
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (134 reviews)
"Well-decorated, coffee/kitchenette setup was great! "
United States
Chandra
The price is HK$969
HK$1,119 total
includes taxes & fees
20 Apr - 21 Apr
The Dylin
Exterior

Cannery Square Short Term Rentals -307 by Patriot

Cannery Square Short Term Rentals -307 by Patriot
Sun Prairie
The price is HK$775
HK$1,845 total
includes taxes & fees
26 Apr - 27 Apr
Cannery Square Short Term Rentals -307 by Patriot
Lobby

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is HK$1,089
HK$1,408 total
includes taxes & fees
20 Apr - 21 Apr
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
Madison
10.0 out of 10, Exceptional, (1 review)
"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$1,657
HK$2,185 total
includes taxes & fees
19 Apr - 20 Apr
Free Breakfast Pool & Hot Tub. Near UW-Madison
Smart TV

Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (40 reviews)
"Wonderful host, and a beautiful home within walking distance to many restaurants and museums. Parking nearby was easy to find. We were able to rest and relax, and make many meals there. Great kitchen amenities, and very comfortable beds. Truly a warm and inviting home. I would highly recommend!"
United States
Jacquie T.
The price is HK$1,332
HK$2,272 total
includes taxes & fees
19 Apr - 20 Apr
Doty ★ Walk to Everything -Hotel Quality- Downtown
Sauna

1 Bedroom - 1220 Canterbury Ct

1 Bedroom - 1220 Canterbury Ct
Sun Prairie
The price is HK$1,150
HK$2,227 total
includes taxes & fees
19 Apr - 20 Apr
1 Bedroom - 1220 Canterbury Ct
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

Home2 Suites by Hilton Madison Central Alliant Energy Center

Home2 Suites by Hilton Madison Central Alliant Energy Center

4/10 Poor
"Breakfast stops too early & no restaurants nearby. Very Very noisey overlooking the highway. Overall crummy hotel tbh"
Theresa 2-night trip
Posted 2 hours ago
Home2 Suites by Hilton Madison Central Alliant Energy Center

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?

Private Pool - Hot Tub - Game Room - 20 min DT: This holiday home rental outside of Windsor offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.