Windsor Holiday Rentals

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Our top choices for Windsor holiday rentals

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 NZ$248
includes taxes & fees
30 Mar - 31 Mar
King Suite | Free Breakfast. Pool and Hot Tub

Cozy Cabin on Crooked Lane close to Lake Wisconsin

Cozy Cabin on Crooked Lane close to Lake Wisconsin
Poynette
The price is NZ$461
includes taxes & fees
5 Apr - 6 Apr
Cozy Cabin on Crooked Lane close to Lake Wisconsin

Cannery Square Unit - 106 by Patriot Properties

Cannery Square Unit - 106 by Patriot Properties
Sun Prairie
9.4 out of 10, Exceptional, (28 reviews)
"Great place "
United States
Armando
The price is NZ$550
includes taxes & fees
30 Mar - 31 Mar
Cannery Square Unit - 106 by Patriot Properties

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 NZ$332
includes taxes & fees
3 Apr - 4 Apr
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

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, (33 reviews)
"Beautiful home, Merrimack is such a quaint town. "
United States
Laura L.
The price is NZ$486
includes taxes & fees
30 Mar - 31 Mar
Updated home with lake views, across the street from Lake Wisc!

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 NZ$701
includes taxes & fees
30 Mar - 31 Mar
2 Bedroom - Main Street Sun Prairie WI

A Pleasant Retreat- No Cleaning Fee & New Discounts

A Pleasant Retreat- No Cleaning Fee & New Discounts
Sun Prairie
10.0 out of 10, Exceptional, (273 reviews)
"Everything was pleasant, location was convenient "
United States
Kelly J.
The price is NZ$551
includes taxes & fees
30 Mar - 31 Mar
A Pleasant Retreat- No Cleaning Fee & New Discounts

Cannery Square Short Term Rentals -307 by Patriot

Cannery Square Short Term Rentals -307 by Patriot
Sun Prairie
The price is NZ$405
includes taxes & fees
2 Apr - 3 Apr
Cannery Square Short Term Rentals -307 by Patriot

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 NZ$255
includes taxes & fees
8 Apr - 9 Apr
Enjoy Nature with Full Comfort!

Cannery Square Short Term Rentals -104 by Patriot

Cannery Square Short Term Rentals -104 by Patriot
Sun Prairie
9.6 out of 10, Exceptional, (47 reviews)
"Spent the Christmas holiday in this cute and spotless unit, which was perfect for us. The host even set out some fun Christmas decorations. It had everything we needed, the host was extremely responsive, and perfect location with a great coffee shop and restaurants within walking distance. I expect we'll do this again."
United States
Marian R.
The price is NZ$558
includes taxes & fees
5 Apr - 6 Apr
Cannery Square Short Term Rentals -104 by Patriot

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 property with a perfect view for fall color. Very comfortable and great space for both couples and family. We enjoyed a very relaxing stay. Host was very prompt with responses and easy to work with."
United States
Jenel S.
The price is NZ$808
includes taxes & fees
13 Apr - 14 Apr
Lakeview Cabin > Unique Mid-Century Tucked in Bluff

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 NZ$991
includes taxes & fees
30 Mar - 31 Mar
Waters Edge Cottage

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 NZ$239
includes taxes & fees
1 Apr - 2 Apr
The Dylin

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is NZ$314
includes taxes & fees
2 Apr - 3 Apr
Pool with Slide. Great for Business Travelers!

Spring Luxury Near Downtown

Spring Luxury Near Downtown
Fitchburg
10.0 out of 10, Exceptional, (20 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 NZ$1,340
includes taxes & fees
30 Mar - 31 Mar
Spring Luxury Near Downtown

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 NZ$531
includes taxes & fees
5 Apr - 6 Apr
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

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 NZ$545
includes taxes & fees
13 Apr - 14 Apr
Doty ★ Walk to Everything -Hotel Quality- Downtown

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)
"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 NZ$862
includes taxes & fees
30 Mar - 31 Mar
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

1 Bedroom - 1220 Canterbury Ct

1 Bedroom - 1220 Canterbury Ct
Sun Prairie
The price is NZ$493
includes taxes & fees
18 Apr - 19 Apr
1 Bedroom - 1220 Canterbury Ct

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 NZ$993
includes taxes & fees
30 Mar - 31 Mar
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown
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

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as NZ$239 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

4 Bed, 3 Bath w/ Pool, Hot Tub, Gym, Fire Pit on Lake Windsor Golf Course: This highly rated holiday home rental in Windsor offers an outdoor pool, a fireplace 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. You can relax into your holiday with 1 hot tub and a selection of books.

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.