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$290
includes taxes & fees
17 May - 18 May
King Suite | Free Breakfast. Pool and Hot Tub

2 Bedroom Apartment Downtown Sun Prairie!

2 Bedroom Apartment Downtown Sun Prairie!
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$673
includes taxes & fees
14 May - 15 May
2 Bedroom Apartment Downtown Sun Prairie!

Cannery Square Short Term Rentals

Cannery Square Short Term Rentals
Sun Prairie
The price is NZ$390
includes taxes & fees
9 June - 10 June
Cannery Square Short Term Rentals

Cozy Cabin on Crooked Lane close to Lake Wisconsin

Cozy Cabin on Crooked Lane close to Lake Wisconsin
Poynette
8.0 out of 10, Very good, (2 reviews)
"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 NZ$477
includes taxes & fees
18 May - 19 May
Cozy Cabin on Crooked Lane close to Lake Wisconsin

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$316
includes taxes & fees
14 May - 15 May
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

Cannery Square Short Term Rentals

Cannery Square Short Term Rentals
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 NZ$533
includes taxes & fees
17 May - 18 May
Cannery Square Short Term Rentals

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 NZ$857
includes taxes & fees
18 May - 19 May
Lakeview Cabin > Unique Mid-Century Tucked in Bluff

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, (3 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$383
includes taxes & fees
17 May - 18 May
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

Enjoy Nature with Full Comfort!

Enjoy Nature with Full Comfort!
Verona
9.2 out of 10, Wonderful, (41 reviews)
"We were visiting friends in the area and it was a perfect spot to stay."
United States
Christine U.
The price is NZ$222
includes taxes & fees
26 May - 27 May
Enjoy Nature with Full Comfort!

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$839
includes taxes & fees
18 May - 19 May
Waters Edge Cottage

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$947
includes taxes & fees
14 May - 15 May
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

1 Bedroom Apartment at Canterbury Court

1 Bedroom Apartment at Canterbury Court
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 NZ$472
includes taxes & fees
14 May - 15 May
1 Bedroom Apartment at Canterbury Court

Entire 3 Bedroom with Fireplace - sleeps 12

Entire 3 Bedroom with Fireplace - sleeps 12
Sun Prairie
9.8 out of 10, Exceptional, (17 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 NZ$992
includes taxes & fees
17 May - 18 May
Entire 3 Bedroom with Fireplace - sleeps 12

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is NZ$301
includes taxes & fees
14 May - 15 May
Pool with Slide. Great for Business Travelers!

The Dylin

The Dylin
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (142 reviews)
"nice location"
United States
Mary
The price is NZ$238
includes taxes & fees
26 May - 27 May
The Dylin

Capital City- 6 Miles from Madison with fireplace

Capital City- 6 Miles from Madison with fireplace
Sun Prairie
9.8 out of 10, Exceptional, (42 reviews)
"Absolutely would stay here again. Tami the host was wonderful, and very responsive. "
United States
Erika O.
The price is NZ$1,043
includes taxes & fees
14 May - 15 May
Capital City- 6 Miles from Madison with fireplace

Free Breakfast. Pool & Hot Tub. Near UW-Madison!

Free Breakfast. Pool & Hot Tub. Near UW-Madison!
Madison
The price is NZ$484
includes taxes & fees
24 May - 25 May
Free Breakfast. Pool & Hot Tub. Near UW-Madison!

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, (52 reviews)
"The location is wonderful. The river setting is beautiful. The pelicans are so fun to watch. Enjoyed all the rooms with tvs."
United States
Robert
The price is NZ$840
includes taxes & fees
26 May - 27 May
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

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, (11 reviews)
"Very comfortable, clean and quiet. Host very accommodating. "
United States
Marisa P.
The price is NZ$828
includes taxes & fees
28 May - 29 May
Bright, Private 3BR Duplex Unit with Parking in Cottage Grove

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$757
includes taxes & fees
14 May - 15 May
Doty ★ Walk to Everything -Hotel Quality- 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$222 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?

Beautifully remodeled 2 bed 104 Berkley Verona #6: This holiday home rental outside of Windsor has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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 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.