Windsor Holiday Rentals

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Check prices for these dates

Tonight
15 Jan - 16 Jan
Tomorrow
16 Jan - 17 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

Our top choices for Windsor holiday rentals

Front of property

The Dylin

The Dylin
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (123 reviews)
"Great stay at the Dylin"
United States
Lauri
The price is HK$786
HK$908 total
includes taxes & fees
18 Jan - 19 Jan
The Dylin
Lobby

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is HK$772
HK$1,048 total
includes taxes & fees
1 Feb - 2 Feb
Pool with Slide. Great for Business Travelers!
Exterior

Cannery Square Short Term Rentals -104 by Patriot

Cannery Square Short Term Rentals -104 by Patriot
Sun Prairie
9.8 out of 10, Exceptional, (46 reviews)
"Roomy. Kitchen had basics. Good beds and pillows. "
United States
Susan
The price is HK$990
HK$2,491 total
includes taxes & fees
19 Jan - 20 Jan
Cannery Square Short Term Rentals -104 by Patriot
Fridge, microwave, oven, stovetop

Charming 3-bedroom Duplex unit with WiFi in Cottage Grove

Charming 3-bedroom Duplex unit with WiFi in Cottage Grove
Village of Cottage Grove
10.0 out of 10, Exceptional, (8 reviews)
"Stayed with friends for the weekend and really enjoyed the home. It was comfortable and had great amenities for our group!"
United States
Anakin F.
The price is HK$1,104
HK$3,501 total
includes taxes & fees
18 Jan - 19 Jan
Charming 3-bedroom Duplex unit with WiFi in Cottage Grove
TV, fireplace, offices

Hot Tub - Game Room - 20 min to Capitol - Pets

Hot Tub - Game Room - 20 min to Capitol - Pets
2.0 star property
Sun Prairie
10.0 out of 10, Exceptional, (1 review)
"I had an excellent stay with Kingdom Hospitality. The home was immaculate, and I enjoyed the updated kitchen. The hot tub was clean, and a great amenity for stress relief. "
United States
Trey B.
Hot Tub - Game Room - 20 min to Capitol - Pets
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$920
HK$1,215 total
includes taxes & fees
6 Feb - 7 Feb
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)
"Clean very friendly nice spot"
Canada
Oliver H.
The price is HK$632
HK$995 total
includes taxes & fees
18 Jan - 19 Jan
Enjoy Nature with Full Comfort!
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$803
HK$1,104 total
includes taxes & fees
18 Jan - 19 Jan
King Suite | Free Breakfast. Pool and Hot Tub
Exterior

Cannery Square Short Term Rentals -102 by Patriot

Cannery Square Short Term Rentals -102 by Patriot
Sun Prairie
8.0 out of 10, Very good, (12 reviews)
"Was cute neighborhood and everything was very clean and close by"
United States
Bri
The price is HK$905
HK$2,140 total
includes taxes & fees
1 Feb - 2 Feb
Cannery Square Short Term Rentals -102 by Patriot
Outdoor dining

Studio Queen in the heart of downtown.

Studio Queen in the heart of downtown.
2.0 star property
Downtown Madison
10.0 out of 10, Exceptional, (1 review)
"Convenient location for events on the Capital Square, State Street and UW-Madison Campus."
United States
Jeffrey W.
The price is HK$1,240
HK$1,639 total
includes taxes & fees
18 Jan - 19 Jan
Studio Queen in the heart of 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
2.0 star property
Middleton
10.0 out of 10, Exceptional, (2 reviews)
"We had a fantastic stay at this property, and it truly exceeded our expectations. The location is excellent—perfectly situated with convenient access to both the east and west sides of Madison, making it easy to get wherever we needed to go. The owners were incredibly helpful and responsive, answering the few questions we had quickly and kindly, which made the entire experience even smoother.One of the biggest highlights for us was the private fenced-in area, which was absolutely perfect for our...
United States
Jessi P.
The price is HK$1,116
HK$2,362 total
includes taxes & fees
18 Jan - 19 Jan
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
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, (38 reviews)
"Clean and quiet. Nice neighborhood amenities. "
United States
Mark L.
The price is HK$1,505
HK$3,149 total
includes taxes & fees
18 Jan - 19 Jan
2 Bedroom - Main Street Sun Prairie WI
Smart TV

Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (37 reviews)
"Beautiful apartment with all we needed for a comfortable family July 4th weekend away!! "
United States
Mindi Z.
The price is HK$1,326
HK$2,208 total
includes taxes & fees
18 Jan - 19 Jan
Doty ★ Walk to Everything -Hotel Quality- Downtown
Sauna

1 Bedroom - 1220 Canterbury Ct

1 Bedroom - 1220 Canterbury Ct
Sun Prairie
The price is HK$1,146
HK$2,202 total
includes taxes & fees
16 Jan - 17 Jan
1 Bedroom - 1220 Canterbury Ct
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$1,755
HK$2,316 total
includes taxes & fees
8 Feb - 9 Feb
Free Breakfast Pool & Hot Tub. Near UW-Madison
Exterior detail

A Pleasant Retreat- No Cleaning Fee & New Discounts

A Pleasant Retreat- No Cleaning Fee & New Discounts
Sun Prairie
10.0 out of 10, Exceptional, (267 reviews)
"Great place and the hosts were great!"
United States
Drew M.
The price is HK$2,144
HK$2,755 total
includes taxes & fees
19 Jan - 20 Jan
A Pleasant Retreat- No Cleaning Fee & New Discounts
Dining

Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Lakeview Cabin > Unique Mid-Century Tucked in Bluff
Merrimac
9.8 out of 10, Exceptional, (22 reviews)
"Everything was exactly as listed and the property was so beautiful. Came with some friends and will definitely try to come back soon! "
United States
Paul G.
The price is HK$1,392
HK$3,075 total
includes taxes & fees
21 Jan - 22 Jan
Lakeview Cabin > Unique Mid-Century Tucked in Bluff
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, (47 reviews)
"Clean and close to everything."
United States
Anonymous traveller
The price is HK$1,861
HK$3,882 total
includes taxes & fees
18 Jan - 19 Jan
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Smart TV, fireplace, printers

Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12
Sun Prairie
9.8 out of 10, Exceptional, (16 reviews)
"Plenty of blankets pillows bed were great"
United States
Kimberly P.
The price is HK$2,729
HK$4,641 total
includes taxes & fees
15 Feb - 16 Feb
Entire 3 Bedroom with Fireplace - sleeps 12
Smart TV, fireplace, stereo, printers

Snowy Madison Escape | Warm Executive Home

Snowy Madison Escape | Warm Executive Home
Fitchburg
10.0 out of 10, Exceptional, (20 reviews)
"Property was generally clean, spacious and had all the amenities that our family needed.An enjoyable stay at a nice property!"
United States
Kim & Jeff T.
The price is HK$2,265
HK$5,858 total
includes taxes & fees
18 Jan - 19 Jan
Snowy Madison Escape | Warm Executive Home
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

Best Western East Towne Suites

Best Western East Towne Suites

10/10 Excellent
"Room was clean. Staff friendly. Great location."
Russell 1-night trip
Posted 1 day ago
Best Western East Towne Suites

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?

A Pleasant Retreat- No Cleaning Fee & New Discounts: This holiday home rental outside of Windsor offers a patio, a garden and a BBQ to help you feel perfectly comfortable 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.