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

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

Caledonia
The price is NZ$1,415 per night from 4 May to 5 May
NZ$1,415
includes taxes & fees
4 May - 5 May
Book a stay at this beach vacation home in Caledonia. Enjoy free WiFi, private pools, and a beach locale. Our guests praise the helpful staff and the property ...
7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool
Charming Vintage Farmhouse 1 bedroom Garden Oasis

Charming Vintage Farmhouse 1 bedroom Garden Oasis

Milwaukee
Stay at this vacation home in Milwaukee. Enjoy a garden, balconies, and an in-room coffeemaker. Popular attractions Henry W. Maier Festival Park and Harley-Davidson ...
Charming Vintage Farmhouse 1 bedroom Garden Oasis
Wonderful craftsman home in Wauwatosa

Wonderful craftsman home in Wauwatosa

Wauwatosa
Stay at this vacation home in Milwaukee. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions American Family Field and ...
Wonderful craftsman home in Wauwatosa
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Charming 3-bedroom house with AC and WiFi in West Allis perfect for pets& family

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

2 out of 5
West Allis
The price is NZ$567 per night from 21 Apr to 22 Apr
NZ$567
includes taxes & fees
21 Apr - 22 Apr
Stay at this vacation home in Milwaukee. Enjoy air conditioning. Popular attractions Wisconsin State Fair Park and Milwaukee County Zoo are located nearby.
Charming 3-bedroom house with AC and WiFi in West Allis perfect for pets& family
Charming 2-bedroom townhome in wonderful Milwaukee

Charming 2-bedroom townhome in wonderful Milwaukee

Milwaukee
Stay at this vacation home in Milwaukee. Enjoy air conditioning. Popular attractions Harley-Davidson Museum and Henry W. Maier Festival Park are located ...
Charming 2-bedroom townhome in wonderful Milwaukee
Warm spacious midsize home w/ comfort and fun

Warm spacious midsize home w/ comfort and fun

Glendale
Stay at this vacation home in Milwaukee. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Fiserv Forum and The Rave-Eagles Club are located ...
Warm spacious midsize home w/ comfort and fun
Charming Vintage Farmhouse 3 Bedroom Oasis

Charming Vintage Farmhouse 3 Bedroom Oasis

Milwaukee
Stay at this vacation home in Milwaukee. Enjoy a garden, balconies, and an in-room coffeemaker. Popular attractions Henry W. Maier Festival Park and Harley-Davidson ...
Charming Vintage Farmhouse 3 Bedroom Oasis
Modern and Convenient Waukesha 3BR home with 2 King Beds

Modern and Convenient Waukesha 3BR home with 2 King Beds

Waukesha
Stay at this vacation home in Waukesha. Enjoy free WiFi, a garden, and patios. Popular attractions Monkey Joe's and Frame Park Formal Gardens are located ...
Modern and Convenient Waukesha 3BR home with 2 King Beds
Cozy Single Family Home Away

Cozy Single Family Home Away

Milwaukee
Stay at this vacation home in Milwaukee. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Milwaukee County Zoo and American Family ...
Cozy Single Family Home Away
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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.

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
Lowest Price
NZ$157
Highest Price
NZ$1,415
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

Top trending hotels in Milwaukee

Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

3 out of 5
700 N. Water Street, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is NZ$219 per night from 27 Apr to 28 Apr
NZ$219
includes taxes & fees
27 Apr - 28 Apr
Stay at this 3-star business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
Drury Plaza Hotel Milwaukee Downtown
Crowne Plaza Milwaukee South by IHG

Crowne Plaza Milwaukee South by IHG

3.5 out of 5
6401 S 13th Street, Milwaukee, WI
Fully refundable
The price is NZ$157 per night from 28 Apr to 29 Apr
NZ$157
includes taxes & fees
28 Apr - 29 Apr
Stay at this 3.5-star business-friendly hotel in Milwaukee. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Crowne Plaza Milwaukee South by IHG
Hilton Milwaukee

Hilton Milwaukee

4 out of 5
509 W Wisconsin Ave, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is NZ$222 per night from 24 Apr to 25 Apr
NZ$222
includes taxes & fees
24 Apr - 25 Apr
Book a stay at this historic hotel in Milwaukee. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
Hilton Milwaukee
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Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave, Milwaukee, WI
The price is NZ$293 per night from 11 May to 12 May
NZ$293
includes taxes & fees
11 May - 12 May
Stay at this 4-star hotel in Milwaukee. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the bar in our reviews. Popular ...
Saint Kate - The Arts Hotel
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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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^Subject to availability and chosen travel dates.