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Featured Holiday Homes in Milwaukee

Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!

Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!

Milwaukee
With a stay at this vacation home, you'll be centrally located in Milwaukee, within a 5-minute drive of Lake Michigan and University of Wisconsin-Milwaukee.
Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities!
Amazing Five Bedroom Milwaukee Vacation Home!!

Amazing Five Bedroom Milwaukee Vacation Home!!

Sussex
Located in Sussex, this vacation home is within a 10-minute drive of Town Hall Clinic and Froedtert Menomonee Falls Hospital.
Amazing Five Bedroom Milwaukee Vacation Home!!
Booth Upper · Amazing view, Modern Space

Booth Upper · Amazing view, Modern Space

Milwaukee
With a stay at this vacation home in Milwaukee (Riverwest), you'll be within a 5-minute drive of Fiserv Forum and Marquette University.
Booth Upper · Amazing view, Modern Space
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NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms

NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms

2 out of 5
Milwaukee
With a stay at this vacation home in Milwaukee (Lower East Side), you'll be within a 5-minute drive of Lake Michigan and Fiserv Forum.
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
Beautiful Waukesha Home

Beautiful Waukesha Home

Waukesha
The price is AU$840 per night from 6 Nov to 7 Nov
AU$840
includes taxes & fees
6 Nov - 7 Nov
A stay at this vacation home places you in the heart of Waukesha, a 5-minute drive from Glacial Drumlin Bike Trail and 5 minutes from Waukesha County ...
Beautiful Waukesha Home
Large, Private 3 Br Home | Ideal Location

Large, Private 3 Br Home | Ideal Location

Milwaukee
With a stay at this vacation home in Milwaukee (Lower East Side), you'll be within a 5-minute drive of Lake Michigan and Fiserv Forum.
Large, Private 3 Br Home | Ideal Location
Heated Pool, Hot Tub, Fishing Pond, Game Room, Weddings,Events!!Read Description

Heated Pool, Hot Tub, Fishing Pond, Game Room, Weddings,Events!!Read Description

Caledonia
With a stay at this vacation home in Caledonia, you'll be on the beach, within a 15-minute drive of Lake Michigan and Ascension SE Wisconsin Hospital - Franklin ...
Heated Pool, Hot Tub, Fishing Pond, Game Room, Weddings,Events!!Read Description
Spacious Pewaukee Lake/ Pier Access Home

Spacious Pewaukee Lake/ Pier Access Home

Pewaukee
With a stay at this vacation home in Pewaukee, you'll be a 1-minute walk from Pewaukee Lake and 13 minutes by foot from Pewaukee Lake Beach.
Spacious Pewaukee Lake/ Pier Access Home
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

Milwaukee
The price is AU$467 per night from 15 Nov to 16 Nov
AU$467
includes taxes & fees
15 Nov - 16 Nov
With a stay at this vacation home in Milwaukee (Johnson Woods), you'll be within a 5-minute drive of American Family Field and Milwaukee County Zoo.
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
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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
322 Holiday Homes
Lowest Price
AU$153
Highest Price
AU$840
Popular accommodation
Modern and Luxurious Milwaukee Home Centrally Located Near Local Amenities! , Amazing Five Bedroom Milwaukee Vacation Home!!, Booth Upper · Amazing view, Modern Space, NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms, Beautiful Waukesha Home, Large, Private 3 Br Home | Ideal Location, Heated Pool, Hot Tub, Fishing Pond, Game Room, Weddings,Events!!Read Description, Spacious Pewaukee Lake/ Pier Access Home, House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

Top trending hotels in Milwaukee

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is AU$231 per night from 28 Nov to 29 Nov
AU$231
includes taxes & fees
28 Nov - 29 Nov
With a stay at Saint Kate - The Arts Hotel, you'll be centrally located in Milwaukee, within a 10-minute walk of Riverside Theater and Fiserv Forum.
Saint Kate - The Arts Hotel
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is AU$265 per night from 2 Dec to 3 Dec
AU$265
includes taxes & fees
2 Dec - 3 Dec
A stay at The Pfister Hotel places you in the heart of Milwaukee, within a 15-minute walk of Lake Michigan and Milwaukee Art Museum.
The Pfister Hotel
Hilton Milwaukee City Center

Hilton Milwaukee City Center

4 out of 5
509 W Wisconsin Ave, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is AU$174 per night from 24 Nov to 25 Nov
AU$174
includes taxes & fees
24 Nov - 25 Nov
With a stay at Hilton Milwaukee City Center, you'll be centrally located in Milwaukee, just a 3-minute walk from Marquette University and 10 minutes by foot ...
Hilton Milwaukee City Center
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Crowne Plaza Milwaukee South, an IHG Hotel

Crowne Plaza Milwaukee South, an IHG Hotel

3.5 out of 5
6401 S 13th Street, Milwaukee, WI
Fully refundable
The price is AU$153 per night from 24 Nov to 25 Nov
AU$153
includes taxes & fees
24 Nov - 25 Nov
Located in Milwaukee (College Heights), Crowne Plaza Milwaukee South, an IHG Hotel is within a 15-minute drive of Milwaukee Public Museum and Harley-Davidson ...
Crowne Plaza Milwaukee South, an IHG 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.