Book Holiday Homes in Milwaukee

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Featured Holiday Homes in Milwaukee

Welcome to the Charming Stone Haven, a beautiful three bedroom property.

Welcome to the Charming Stone Haven, a beautiful three bedroom property.

Milwaukee WI
Stay at this family-friendly holiday home in Milwaukee. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions American Family Field and Milwaukee ...
Opens in a new windowWelcome to the Charming Stone Haven, a beautiful three bedroom property.
Three bedrooms upstairs

Three bedrooms upstairs

Milwaukee WI
Stay at this business-friendly holiday home in Milwaukee. Enjoy free Wi-Fi, breakfast (surcharge) and a garden. Popular attractions Fiserv Forum and Milwaukee ...
Opens in a new windowThree bedrooms upstairs
Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub

Waukesha WI
The price is NZ$533 per night from 12 May to 13 May
NZ$533
12 May - 13 May
includes taxes & fees
Stay at this holiday home in Waukesha. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Monkey Joe's and Prairieville Park are located ...
Opens in a new windowModern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub
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Quiet House

Quiet House

Milwaukee WI
Stay at this holiday home in Milwaukee. Enjoy an in-room coffee maker and in-room fireplaces. Popular attractions Potawatomi Bingo Casino and Fiserv Forum are ...
Opens in a new windowQuiet House
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

Milwaukee WI
The price is NZ$566 per night from 7 May to 8 May
NZ$566
7 May - 8 May
includes taxes & fees
Stay at this holiday home in Milwaukee. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions American Family Field and Milwaukee County Zoo ...
Opens in a new windowHouse in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
The Gem of Brewers Hill with hot tub and seasonal pool

The Gem of Brewers Hill with hot tub and seasonal pool

Milwaukee WI
Stay at this holiday home in Milwaukee. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Fiserv Forum and Milwaukee Art Museum are located ...
Opens in a new windowThe Gem of Brewers Hill with hot tub and seasonal pool
Remodeled Luxury 3BR - Walk to Cedarburg Downtown

Remodeled Luxury 3BR - Walk to Cedarburg Downtown

Cedarburg WI
The price is NZ$749 per night from 11 May to 12 May
NZ$749
11 May - 12 May
includes taxes & fees
Stay at this holiday home in Cedarburg. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Cedarburg Cultural Center and Cedar ...
Opens in a new windowRemodeled Luxury 3BR - Walk to Cedarburg Downtown
Wonderful craftsman home in Wauwatosa

Wonderful craftsman home in Wauwatosa

Wauwatosa WI
Stay at this holiday home in Milwaukee. Enjoy laundry facilities, patios and cable/satellite TV service. Popular attractions American Family Field and Milwaukee ...
Opens in a new windowWonderful craftsman home in Wauwatosa
Modern Lux Home, Sleeps 12, Walk to Brady St Fun

Modern Lux Home, Sleeps 12, Walk to Brady St Fun

Milwaukee WI
Stay at this holiday home in Milwaukee. Enjoy laundry facilities and air conditioning. Popular attractions Milwaukee Art Museum and Fiserv Forum are located ...
Opens in a new windowModern Lux Home, Sleeps 12, Walk to Brady St Fun
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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
394 Holiday Homes
Lowest Price
NZ$202
Highest Price
NZ$749
Popular accommodation
Welcome to the Charming Stone Haven, a beautiful three bedroom property., Three bedrooms upstairs , Modern and Convenient Waukesha 3BR home with 2 King Beds and Hot Tub, Quiet House, House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!, The Gem of Brewers Hill with hot tub and seasonal pool, Remodeled Luxury 3BR - Walk to Cedarburg Downtown, Wonderful craftsman home in Wauwatosa, Modern Lux Home, Sleeps 12, Walk to Brady St Fun

Top trending hotels in Milwaukee

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
1611 West Canal Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is NZ$297 per night from 11 May to 12 May
NZ$297
11 May - 12 May
includes taxes & fees
Stay at this luxury hotel in Milwaukee. Enjoy free Wi-Fi, free parking and 7 restaurants. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowPotawatomi Hotel & Casino
The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
500 W Florida Street Milwaukee WI
The price is NZ$318 per night from 31 May to 1 June
NZ$318
31 May - 1 June
includes taxes & fees
Stay at this boutique hotel in Milwaukee. Enjoy free Wi-Fi, 3 restaurants and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowThe Iron Horse Hotel
Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
The price is NZ$202 per night from 10 May to 11 May
NZ$202
10 May - 11 May
includes taxes & fees
Stay at this golf hotel in Brookfield. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowSheraton Milwaukee Brookfield Hotel
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Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

3 out of 5
700 N. Water Street Milwaukee WI
The price is NZ$222 per night from 25 May to 26 May
NZ$222
25 May - 26 May
includes taxes & fees
Stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free Wi-Fi and a 24-hour fitness centre. Our guests praise the breakfast and the pool ...
Opens in a new windowDrury Plaza Hotel Milwaukee Downtown
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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.