A park with a statue of a figure on horseback, surrounded by leafless trees and a clear sky.

Windsor Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Windsor holiday rentals

Reception

The Dylin

The Dylin
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (160 reviews)
"Amazing"
United States
Jennifer
The price is HK$1,274
HK$1,472 total
includes taxes & fees
9 Aug - 10 Aug
The Dylin
4 bedrooms, iron/ironing board, free WiFi, bed sheets

Capital City- 6 Miles from Madison with fireplace

Capital City- 6 Miles from Madison with fireplace
Sun Prairie
9.8 out of 10, Exceptional, (48 reviews)
"Very nice place"
United States
Penny C.
The price is HK$2,940
HK$4,939 total
includes taxes & fees
25 Jul - 26 Jul
Capital City- 6 Miles from Madison with fireplace
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, (20 reviews)
"Fantastic Stay!! Host was great to work with!"
United States
Heather H.
The price is HK$2,838
HK$4,798 total
includes taxes & fees
11 Aug - 12 Aug
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
Terrace/patio

Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool

Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
Madison
10.0 out of 10, Exceptional, (1 review)
"Clean, quiet, and convenient! Everything went smooth."
United States
Thomas C.
The price is HK$1,568
HK$2,074 total
includes taxes & fees
2 Aug - 3 Aug
Accessible 1BR Suite w/ Tub | Hot Breakfast + Pool
3 bedrooms, free WiFi, bed sheets

Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12
Sun Prairie
10.0 out of 10, Exceptional, (21 reviews)
"This was the perfect size home for a holiday family get together. Nice common spaces with enough areas to go when a little alone time was needed "
United States
Steve S.
The price is HK$2,744
HK$4,648 total
includes taxes & fees
22 Jul - 23 Jul
Entire 3 Bedroom with Fireplace - sleeps 12
Terrace/patio

Free Breakfast Pool & Hot Tub. Near East Towne Mall!

Free Breakfast Pool & Hot Tub. Near East Towne Mall!
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$2,127
HK$2,820 total
includes taxes & fees
2 Aug - 3 Aug
Free Breakfast Pool & Hot Tub. Near East Towne Mall!
Exterior

2 Bed/ 2 Bath At Cannery Square

2 Bed/ 2 Bath At Cannery Square
Sun Prairie
9.8 out of 10, Exceptional, (51 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$1,098
HK$2,664 total
includes taxes & fees
2 Aug - 3 Aug
2 Bed/ 2 Bath At Cannery Square
Outdoor dining

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
Dane
10.0 out of 10, Exceptional, (2 reviews)
"Feeding the horses was so fun and the scenery is very picturesque. Wonderful place to stay!"
United States
Katelyn F.
The price is HK$1,301
HK$2,131 total
includes taxes & fees
29 Jul - 30 Jul
Escape to tranquility – your countryside haven, and at times with a horse or two
TV, fireplace, table football, offices

Hot Tub - King Suite - Game Room - Large Groups

Hot Tub - King Suite - Game Room - Large Groups
Sun Prairie
10.0 out of 10, Exceptional, (22 reviews)
"An amazing house, great location, it was the most wonderfully supplied VRBO ever!"
United States
George P.
The price is HK$2,321
HK$7,051 total
includes taxes & fees
29 Jul - 30 Jul
Hot Tub - King Suite - Game Room - Large Groups
Exterior

2 Bed/ 2 Bath At Cannery Square

2 Bed/ 2 Bath At Cannery Square
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$1,333
HK$2,955 total
includes taxes & fees
11 Aug - 12 Aug
2 Bed/ 2 Bath At Cannery Square
Sauna

Cozy 1 Bedroom Apartment with King Bed & Patio Near Madison

Cozy 1 Bedroom Apartment with King Bed & Patio Near Madison
Sun Prairie
8.0 out of 10, Very good, (2 reviews)
"Great for what our trip was for. Quiet. Pet friendly. Good location"
United States
Robert M.
The price is HK$909
HK$1,923 total
includes taxes & fees
13 Aug - 14 Aug
Cozy 1 Bedroom Apartment with King Bed & Patio Near Madison
Coffee/tea maker, fridge, microwave, oven

Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Village of Cottage Grove
10.0 out of 10, Exceptional, (13 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
The price is HK$1,853
HK$4,533 total
includes taxes & fees
3 Aug - 4 Aug
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove
Exterior

Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
The price is HK$776
HK$1,893 total
includes taxes & fees
2 Aug - 3 Aug
Studio Apartment at Cannery Square
Exterior

Studio Apartment at Cannery Square

Studio Apartment at Cannery Square
Sun Prairie
8.2 out of 10, Very good, (14 reviews)
"Was cute neighborhood and everything was very clean and close by"
United States
Bri
Studio Apartment at Cannery Square
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$1,103
HK$1,450 total
includes taxes & fees
2 Aug - 3 Aug
King Suite | Free Breakfast. Pool and Hot Tub
Terrace/patio

Free Breakfast. Pool & Hot Tub. Near East Towne Mall!

Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
Madison
The price is HK$2,127
HK$2,820 total
includes taxes & fees
2 Aug - 3 Aug
Free Breakfast. Pool & Hot Tub. Near East Towne Mall!
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, (53 reviews)
"Great little lake house, close to downtown Madison. "
United States
LiHsin C.
The price is HK$1,900
HK$3,990 total
includes taxes & fees
3 Aug - 4 Aug
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, (9 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$1,058
HK$1,793 total
includes taxes & fees
18 Aug - 19 Aug
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Terrace/patio

Badger Digs - A Lofted Condo on the Wisconsin River

Badger Digs - A Lofted Condo on the Wisconsin River
Poynette
10.0 out of 10, Exceptional, (21 reviews)
"What a great place to stay for just a couple or a family! The host was so easy to communicate with and we had a wonderful time! "
United States
Heather B.
The price is HK$1,176
HK$2,316 total
includes taxes & fees
28 Jul - 29 Jul
Badger Digs - A Lofted Condo on the Wisconsin River
Outdoor dining

A Room with a View

A Room with a View
Verona
9.2 out of 10, Wonderful, (49 reviews)
The price is HK$649
HK$1,016 total
includes taxes & fees
4 Aug - 5 Aug
A Room with a View
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

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

10/10 Excellent
"They gave us a shuttle to see phish for five bucks. It was unexpected, but really a nice surprise. Hotel was wonderful. Would highly recommend."
William 2-night trip
Posted 4 hours ago
The Madison Concourse Hotel and Governor's Club

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?

Waterfront Lodi Vacation Rental on Lake Wisconsin!: This holiday home rental outside of Windsor is located on the waterfront, and has a patio, a selection of games and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Windsor?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Windsor stay.

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 Barrymore Theatre.

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.