A city skyline with modern skyscrapers and a river in the foreground.

Search Vacation Homes in Milwaukee

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Milwaukee holiday homes

A bathroom with a towel rack, a soap dispenser, and a shower stall.

1. Quiet House

Quiet House
Milwaukee
7.6 out of 10, Good, (22 reviews)
"The house was clean, the neighborhood was quiet. The house was very close to the Baird center and other places we wanted to visit."
United States
Steven
The price is HK$530
HK$1,661 total
includes taxes & fees
12 Oct - 13 Oct
Quiet House
A modern kitchen with white cabinets, a stainless steel stove, and a wooden countertop.

2. Remodeled Home - Steps from Brady Street!

Remodeled Home - Steps from Brady Street!
Downtown Milwaukee
10.0 out of 10, Exceptional, (12 reviews)
"Great stay and great communication throughout. Would stay again, thank you!"
United States
David M.
The price is HK$549
HK$2,304 total
includes taxes & fees
28 Oct - 29 Oct
Remodeled Home - Steps from Brady Street!
A modern living room with a sofa, a coffee table, and a TV with a mirror above it.

3. Serene 3-Bedroom Milwaukee Retreat Basketball Court & Fitness Room

Serene 3-Bedroom Milwaukee Retreat Basketball Court & Fitness Room
Westown
10.0 out of 10, Exceptional, (1 review)
"Great location. Secure building. Well maintained and clean. Responsive host via text."
United States
Irvin J.
The price is HK$1,562
HK$2,951 total
includes taxes & fees
27 Oct - 28 Oct
Serene 3-Bedroom Milwaukee Retreat Basketball Court & Fitness Room
Interior

4. The Pink Lady - Stylish Walker’s Point Home

The Pink Lady - Stylish Walker’s Point Home
Fifth Ward
9.6 out of 10, Exceptional, (9 reviews)
"Great time. Fun place to stay"
United States
syed a.
The price is HK$793
HK$2,470 total
includes taxes & fees
4 Nov - 5 Nov
The Pink Lady - Stylish Walker’s Point Home
A room with a wooden floor, a television on a stand, a white door, and a window with a view of buildings outside.

5. Best location in Milwaukee! Upper Duplex Unit

Best location in Milwaukee! Upper Duplex Unit
Downtown Milwaukee
8.6 out of 10, Excellent, (24 reviews)
"Overall good stay in a charming Milwaukee duplex. Primary bedroom could use some blackout curtains. Shower/tub is a little small."
United States
Laura R.
The price is HK$578
HK$1,322 total
includes taxes & fees
12 Oct - 13 Oct
Best location in Milwaukee! Upper Duplex Unit
Private kitchen

6. The Bentley - Frida's Reign, Heart of Walkers Point w/Garage,Yard

The Bentley - Frida's Reign, Heart of Walkers Point w/Garage,Yard
Fifth Ward
10.0 out of 10, Exceptional, (7 reviews)
"Loved our stay - owner thought of everything - toiletries, coffee, snacks, cell phone chargers and so much more! Will stay here again."
United States
Holly B.
The price is HK$965
HK$2,350 total
includes taxes & fees
18 Oct - 19 Oct
The Bentley - Frida's Reign, Heart of Walkers Point w/Garage,Yard
A spacious living room with a large TV, a wooden coffee table, and a gray sofa. There is a dining area with a table and chairs, and a kitchen area with a fridge and a microwave.

7. Barclay House in Walker's Point

Barclay House in Walker's Point
Fifth Ward
10.0 out of 10, Exceptional, (11 reviews)
"Very nice and comfortable home."
United States
Tom L.
The price is HK$1,624
HK$2,942 total
includes taxes & fees
9 Oct - 10 Oct
Barclay House in Walker's Point
A modern living room with a sofa, a coffee table, and a television mounted on the wall.

8. Near Lake Michigan • Coffee Bar • Workspace

Near Lake Michigan • Coffee Bar • Workspace
Milwaukee
The price is HK$710
HK$4,265 total
includes taxes & fees
12 Oct - 13 Oct
Near Lake Michigan • Coffee Bar • Workspace
A spacious hallway with wooden flooring, a central dining table with chairs, a chandelier, and a bookshelf with books.

9. Three Bedroom Upper

Three Bedroom Upper
Riverwest
9.6 out of 10, Exceptional, (104 reviews)
"Close to everything in Milwaukee"
United States
Terri E.
The price is HK$1,377
HK$1,837 total
includes taxes & fees
11 Oct - 12 Oct
Three Bedroom Upper
A spacious living room with a spiral staircase, wooden flooring, a large potted plant, and a modern air conditioning unit.

10. Fun, style & comfort Eastside downtown 4 bedroom townhome near attractions

Fun, style & comfort Eastside downtown 4 bedroom townhome near attractions
Lower East Side
9.6 out of 10, Exceptional, (44 reviews)
"Great location to Brady Street."
United States
Andrew C.
The price is HK$1,363
HK$3,772 total
includes taxes & fees
12 Oct - 13 Oct
Fun, style & comfort Eastside downtown 4 bedroom townhome near attractions
A modern kitchen with dark cabinets, a white stove, and a dining area with a table and chairs.

11. Upper Pro Retreat near Hospitals - 30 day min - Garage & Yard. Dog-friendly!

Upper Pro Retreat near Hospitals - 30 day min - Garage & Yard. Dog-friendly!
Fair Park
10.0 out of 10, Exceptional, (3 reviews)
"I chose this area to visit family, once again, Lorinda was the best! I will visit again soon. "
United States
AnnaLisa S.
The price is HK$824
HK$2,683 total
includes taxes & fees
5 Nov - 6 Nov
Upper Pro Retreat near Hospitals - 30 day min - Garage & Yard. Dog-friendly!
A living room with a ceiling fan, a sofa, a coffee table, and a dining area with a table and chairs.

12. Charming Bungalow / Heart of Bay View / Parking - Central Air - Deck

Charming Bungalow / Heart of Bay View / Parking - Central Air - Deck
Bay View
10.0 out of 10, Exceptional, (39 reviews)
"Great place to stay in Milwaukee! The house was clean and very well stocked with everything we could need! I didn’t realize someone lived upstairs, but there wasn’t any issues with it. The neighborhood was close to many great things to do We would definitely stay here again!"
United States
Jenna H.
The price is HK$1,413
HK$3,488 total
includes taxes & fees
12 Oct - 13 Oct
Charming Bungalow / Heart of Bay View / Parking - Central Air - Deck
A neatly made bed with white bedding, a vase with flowers, a tray with a cup and saucer, and a magazine on the bed.

13. Workspace • Fireplace • Coffee Bar • Sleeps 12

Workspace • Fireplace • Coffee Bar • Sleeps 12
Milwaukee
6.0 out of 10, (2 reviews)
"The house was nice and accommodated our travel greatly. Communication before and during the stay from the host, was spot on. Everything went smoothly."
United States
Chris B.
The price is HK$635
HK$4,132 total
includes taxes & fees
14 Oct - 15 Oct
Workspace • Fireplace • Coffee Bar • Sleeps 12
A courtyard with a wooden fence, a gravel path, and a variety of plants.

14. Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find

Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
Lower East Side
9.4 out of 10, Exceptional, (75 reviews)
"Clean, strong communication, great location. Thank you!"
United States
Jenna L.
The price is HK$1,406
HK$3,249 total
includes taxes & fees
12 Oct - 13 Oct
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
A room with a sofa, a glass coffee table, a lamp, and a door.

15. Entire Designer Building, Sleeps 13

Entire Designer Building, Sleeps 13
Lower East Side
The price is HK$1,648
HK$5,205 total
includes taxes & fees
12 Oct - 13 Oct
Entire Designer Building, Sleeps 13
A living room with a sofa, coffee table, TV, and a view of a green landscape.

16. King Bed • Vintage Urban Oasis • Near MKE Airport

King Bed • Vintage Urban Oasis • Near MKE Airport
Town of Lake
"Small place perfect for a solo traveler or a small family. Cute mix of old and new furnishings and decor. Updated fixtures and appliances. Had everything needed in the kitchen space to grocery shop and eat it. I was traveling for work and needed a home away from home without much fuss and this place checked at the boxes.."
United States
Rachel C.
The price is HK$1,093
HK$2,122 total
includes taxes & fees
12 Oct - 13 Oct
King Bed • Vintage Urban Oasis • Near MKE Airport
A living room with a flat-screen TV, two sofas, a coffee table, and a large window with wooden frames.

17. Sunny & Spacious 4BR East Side Stay ¦ Balcony ¦ Family-Friendly

Sunny & Spacious 4BR East Side Stay ¦ Balcony ¦ Family-Friendly
Upper East Side
9.2 out of 10, Wonderful, (13 reviews)
"Great stay!The house was perfect for us with an excellent location."
United States
Mike G.
The price is HK$1,166
HK$2,704 total
includes taxes & fees
28 Oct - 29 Oct
Sunny & Spacious 4BR East Side Stay ¦ Balcony ¦ Family-Friendly
A Victorian-style house with a prominent front staircase, multiple windows, and lush greenery.

18. Classic Victorian with modern amenities in the heart of Downtown Milwaukee

Classic Victorian with modern amenities in the heart of Downtown Milwaukee
Downtown Milwaukee
8.8 out of 10, Excellent, (11 reviews)
"Perfect location had a great time "
United States
Andrew H.
The price is HK$2,550
HK$4,969 total
includes taxes & fees
1 Nov - 2 Nov
Classic Victorian with modern amenities in the heart of Downtown Milwaukee
A deck with a table, chairs, and an umbrella.

19. Luxurious Craftsman Style Home in Famous Bay View with Hot Tub Oasis

Luxurious Craftsman Style Home in Famous Bay View with Hot Tub Oasis
Milwaukee
The price is HK$1,491
HK$4,811 total
includes taxes & fees
29 Oct - 30 Oct
Luxurious Craftsman Style Home in Famous Bay View with Hot Tub Oasis
A living room with a blue sofa, a round coffee table, and a view of a blue house through a large window.

20. Central location, newly remodeled, Backyard, Firepit, Hot Tub, A/C, Pet-Friendly

Central location, newly remodeled, Backyard, Firepit, Hot Tub, A/C, Pet-Friendly
Murray Hill
10.0 out of 10, Exceptional, (18 reviews)
"Beautiful house, excellent location, attentive host! It was a great stay! "
United States
Cary W.
The price is HK$1,540
HK$4,258 total
includes taxes & fees
11 Oct - 12 Oct
Central location, newly remodeled, Backyard, Firepit, Hot Tub, A/C, Pet-Friendly
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Milwaukee Hotel Reviews

Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

10/10 Excellent
"Friendly staff, clean rooms/amenities."
Thi Nga 1-night trip
Posted 3 hours ago
Hyatt Regency Milwaukee

Find out more about Milwaukee

Milwaukee Vacation Homes information

Number of reviews
259
Accommodation
345 Vacation Homes
Lowest Price
HK$1,322
Highest Price
HK$5,205

Explore a world of travel with Expedia