Milwaukee Holiday Rentals

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Our top choices for Milwaukee holiday rentals

The Plaza Hotel

The Plaza Hotel
3.0 star property
Downtown Milwaukee
8.8 out of 10, Excellent, (1153)
"From check in to check out excellent stay!"
United States
Heather
The price is NZ$282
includes taxes & fees
18 Jan - 19 Jan 2026
The Plaza Hotel

Kasa Westown Milwaukee

Kasa Westown Milwaukee
4.0 star property
Westown
9.0 out of 10, Wonderful, (120)
"Hosts get 5 stars for excellent communication. They checked in with me multiple times on my day of arrival to make sure everything was good and they gave very thorough instructions."
United States
Melissa
Kasa Westown Milwaukee

Large Milwaukee Home 4BR Fast Wifi

Large Milwaukee Home 4BR Fast Wifi
3.0 star property
Fifth Ward
The price is NZ$1,262
includes taxes & fees
11 Jan - 12 Jan 2026
Large Milwaukee Home 4BR Fast Wifi

Brew City Game Room Fenced Yard Sleeps 13

Brew City Game Room Fenced Yard Sleeps 13
2.0 star property
Wauwatosa
10.0 out of 10, Exceptional, (1)
"Amazing location off the highway was able to make it into the city efficiently. Would recommend!"
United States
Dario
The price is NZ$850
includes taxes & fees
27 Jan - 28 Jan 2026
Brew City Game Room Fenced Yard Sleeps 13
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 Milwaukee Hotel Reviews

Find out more about Milwaukee

Everything you need to know about Milwaukee 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 Milwaukee 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 Milwaukee holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Milwaukee holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Milwaukee. 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 Milwaukee 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 Milwaukee holiday rentals we have selected for you start as low as NZ$282 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Milwaukee rentals

At Expedia, we put the best Milwaukee 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 Milwaukee 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 Milwaukee 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 Milwaukee. 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

Are there holiday rentals in Milwaukee?

Yes, there are holiday rentals in Milwaukee close to Betty Brinn Children's Museum, or you can select a more secluded option if you're looking for a relaxing stay. Travellers who like culture and the arts give Milwaukee high marks for its fascinating museums and entertainment choices. The lively festivals and great live music are some other things you might like to check out during your trip.

What are some of the best holiday rentals that Milwaukee has to offer?

Deluxe Dwelling 4Br, 2Ba| Sunlit, Spacious, Serine: This highly rated holiday home rental in Milwaukee is located in the city centre, and has a balcony, an arcade/games room and air conditioning to put you at ease 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. Some other top choices in Milwaukee are Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find and Three bedrooms upstairs .

How many holiday rentals are there in Milwaukee?

Choose from 529 Expedia holiday rentals in Milwaukee for a memorable holiday.

What can I see and do in Milwaukee?

Cultural attractions include Marcus Center for the Performing Arts and Riverside Theater, whereas Lake Michigan and Lakeshore State Park are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Pabst Theater and Milwaukee Public Market.

What’s a holiday rental in Milwaukee like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Milwaukee. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.