Book Holiday Homes in Milwaukee
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Featured Holiday Homes in Milwaukee

7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool

Charming Vintage Farmhouse 1 bedroom Garden Oasis

Wonderful craftsman home in Wauwatosa

Charming 3-bedroom house with AC and WiFi in West Allis perfect for pets& family

Charming 2-bedroom townhome in wonderful Milwaukee

Warm spacious midsize home w/ comfort and fun

Charming Vintage Farmhouse 3 Bedroom Oasis

Modern and Convenient Waukesha 3BR home with 2 King Beds

Cozy Single Family Home Away
Milwaukee Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Milwaukee vacation homes are the perfect way for you to wing it.
Holiday houses in Milwaukee let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Milwaukee in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Milwaukee adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Milwaukee with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Milwaukee vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Milwaukee Holiday Homes essential information
Accommodation | 404 Holiday Homes |
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Lowest Price | NZ$229 |
Highest Price | NZ$939 |
Popular accommodation | 7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool, Charming Vintage Farmhouse 1 bedroom Garden Oasis, Wonderful craftsman home in Wauwatosa, Charming 3-bedroom house with AC and WiFi in West Allis perfect for pets& family, Charming 2-bedroom townhome in wonderful Milwaukee , Warm spacious midsize home w/ comfort and fun, Charming Vintage Farmhouse 3 Bedroom Oasis, Modern and Convenient Waukesha 3BR home with 2 King Beds, Cozy Single Family Home Away |
More accommodations in Milwaukee
Top trending hotels in Milwaukee

Drury Plaza Hotel Milwaukee Downtown

The Pfister Hotel

Potawatomi Hotel & Casino

Saint Kate - The Arts Hotel
More ways to explore Milwaukee
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^Subject to availability and chosen travel dates.