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Windsor Holiday Rentals

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Holiday Rentals in Windsor

The Dylin by Mint House

4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (113)
"Great location and very comfortable stay. Love the extra space to hang out."
United States
Brian
The Dylin by Mint House

Lake Wisconsin Resort

3.0 star property
Poynette
10.0 out of 10, Exceptional, (1)
"The cabins looked small from the outside, but we're actually very spacious we didn't feel cramped everything was very clean there was a full kitchen a table big enough to sit at least four. I think the only thing that wasn't 100% perfect was the beds are a little small they were stiff and the pillows were also very small and serviceable. I would still definitely stay there again 100% and would recommend it to everyone!"
United States
Shelley
Lake Wisconsin Resort

Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!

Poynette
9.8 out of 10, Exceptional, (250)
"Hot tub over looking the water was amazing, relaxing and so peaceful"
United States
Sherri S.
Quietwater Cottage-On Water/Nature/Birds/Canoe/Hike/Relaxing/ Hot Tub, Peaceful!

Capital PrimeTime - 6 Miles from Madison w/ fireplace

Sun Prairie
9.8 out of 10, Exceptional, (30)
"Would recommend - very good location, nice space, and great host!"
United States
James O.
The price is NZ$1,117
includes taxes & fees
11 Nov - 12 Nov
Capital PrimeTime - 6 Miles from Madison w/ fireplace

Private Pool - HOT TUB - Sauna - Game Room - Pets

Sun Prairie
10.0 out of 10, Exceptional, (6)
"The Sun Prairie house perfectly met the goals for our family gathering of six adults and golden retriever for social and private space and so many entertainment options! The house was spotless, the neighborhood quiet, with Woodmans close by for shopping. We had 5 days of sunshine, golfing nearby courses, enjoying afternoon pool time, evening hot tub, and bug-free outdoor dining-so private and relaxing! We never ran out of room for food/drinks in the large volume fridge (loved the beverage...
United States
Patricia M.
The price is NZ$1,543
includes taxes & fees
12 Nov - 13 Nov
Private Pool - HOT TUB - Sauna - Game Room - Pets

Doty ★ Walk to Everything -Hotel Quality- Downtown

Downtown Madison
9.8 out of 10, Exceptional, (35)
"Great location, family friendly. Would stay again!"
United States
Sarah S.
The price is NZ$559
includes taxes & fees
1 Dec - 2 Dec
Doty ★ Walk to Everything -Hotel Quality- Downtown

Historic Home Near Wi Dells, Lake Wi & Party Space Avail!

Merrimac
8.2 out of 10, Very good, (23)
"Big old house that had plenty of room for all our extended family."
United States
Samuel Z.
Historic Home Near Wi Dells, Lake Wi & Party Space Avail!

COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!

Lodi
10.0 out of 10, Exceptional, (100)
"Great location, beautiful views, cozy cabin. "
United States
Chris M.
COZY WATERFRONT CABIN, ON SUNSET BAY, LAKE WISCONSIN !! SUMMER AND WINTER FUN !!

Pool with Slide. Great for Business Travelers!

Fitchburg
The price is NZ$306
includes taxes & fees
13 Nov - 14 Nov
Pool with Slide. Great for Business Travelers!

Free Breakfast Pool & Hot Tub. Near UW-Madison

Madison
10.0 out of 10, Exceptional, (1)
"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 NZ$546
includes taxes & fees
23 Nov - 24 Nov
Free Breakfast Pool & Hot Tub. Near UW-Madison

Island View Hideaway-Peaceful, On Water, Canoe, Scenic, Birds, Nature, Sandbars!

Poynette
9.8 out of 10, Exceptional, (210)
"Traveled from Milwaukee for the beauty and peacefulness of nature by the Wisconsin River. We enjoyed our stay in this very nice home with a great location. Well cared for property and we’d definitely return!!"
United States
Laura L.
Island View Hideaway-Peaceful, On Water, Canoe, Scenic, Birds, Nature, Sandbars!

Contemporary home in quiet neighborhood with pool & great back yard close to all

Middleton
9.6 out of 10, Exceptional, (10)
"Very nice co overall."
United States
Tina E.
Contemporary home in quiet neighborhood with pool & great back yard close to all

Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Merrimac
9.8 out of 10, Exceptional, (20)
"Great property, beautiful view, very unique design on this property. The property was well prepared for our visit. Just sits on the side of a hill with a view in the distance of the Wisconsin River. I highly recommend it."
United States
Jay T.
The price is NZ$703
includes taxes & fees
10 Dec - 11 Dec
Lakeview Cabin > Unique Mid-Century Tucked in Bluff

Exceptional 4 Bed 3 Bath Hot tub next to woods -Comfortable! - 21 min to Madison

Deerfield
10.0 out of 10, Exceptional, (132)
"the house has ample room and amenities with a great screened-in porch and large kitchen. very clean and nicely decorated. peaceful neighborhood. everyone was extremely comfortable and beds are comfortable. our 3-year old grandson was so excited to see hundreds of fireflies at dusk in the yard. everything was well thought-out and we loved that the kitchen is so well equipped. "
United States
Matias V.
Exceptional 4 Bed 3 Bath Hot tub next to woods -Comfortable! - 21 min to Madison

Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

Faircrest
10.0 out of 10, Exceptional, (118)
"This property is perfect for a weekend in Madison. It was clean, easy-going, and fun. 11/10! "
United States
Mariano M.
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

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

Sun Prairie
10.0 out of 10, Exceptional, (11)
"Perfect property for our group, will definitely be back.Immaculately maintained, excellent kitchen for preparing large group meals. Would recommend visitors bring spices, dried goods (flour, sugar, etc), storage containers/bags, wraps/foils and extra paper towels. If you forget there is excellent shopping and food options within 5 to 7 minute drive (costco, woodmans, aldi).Host was reaponsive leading up to our trip and extremely friendly and flexible. Even did a call with me to ensure we would...
United States
Nick he-him M.
The price is NZ$1,026
includes taxes & fees
11 Nov - 12 Nov
Citys EDGE of Madison- SLEEPS 10 & ONLY 6 Miles to downtown

ONE OF A KIND vacation rental with a view

Madison
10.0 out of 10, Exceptional, (146)
"This is our second stay and will gladly come back. It is easy to maneuver around Madison and the house is a spectacular vintage 80’s home. "
United States
Deborah C.
ONE OF A KIND vacation rental with a view

On the Yahara River, access to Madison Lakes

Monona
10.0 out of 10, Exceptional, (49)
"The house and hosts were both lovely! We had a great weekend and would definitely book the Doll House again for another Madison getaway! Thank you!!"
United States
Christine W.
On the Yahara River, access to Madison Lakes

Enjoy Nature with Full Comfort!

Verona
9.4 out of 10, Exceptional, (35)
"I enjoyed this location. Was the perfect size for one person (or a couple’s getaway). The room was secure and safe. Clean and had some nice little extras in the room. Marca was very attentive to all communication we had. The scenery out the big bay window was lovely as well. Would stay again if the opportunity arose."
United States
Jennifer B.
The price is NZ$227
includes taxes & fees
17 Nov - 18 Nov
Enjoy Nature with Full Comfort!

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Monona
9.8 out of 10, Exceptional, (47)
"We absolutely loved this place! Perfect spot with a pier on the water. My kids were catching fish within minutes. The house was perfect and Jake couldn’t have been easier to work with. Highly recommend! "
United States
Mark G.
The price is NZ$886
includes taxes & fees
11 Nov - 12 Nov
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes 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$227 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?

Private Pool - HOT TUB - Sauna - Game Room - Pets: 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 5 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.