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Milwaukee Holiday Rentals

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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 rentals

A bedroom with a bed, bedside table, nightstand, ceiling fan, potted plant, window with blinds, and artwork on the wall.

1. The Plaza Hotel

The Plaza Hotel
3.0 star property
Downtown Milwaukee
8.8 out of 10, Excellent, (1,256 reviews)
"Parking was reasonable and close by"
United States
Danita
The price is HK$1,129
HK$1,331 total
includes taxes & fees
2 Nov - 3 Nov
The Plaza Hotel
A multi-story building with a prominent entrance, large windows, and a flag.

2. Luxury Downtown Apt with Parking, Gym, and Lap Pool · Sleeps 4-5

Luxury Downtown Apt with Parking, Gym, and Lap Pool · Sleeps 4-5
Downtown Milwaukee
10.0 out of 10, Exceptional, (13 reviews)
"Great place and location. Loved that underground secured parking was included in the price. Excellent communication and easy check in/out instructions. She was very responsive. The bed was very comfortable and the sheets were very soft. Overall a great stay. Would definitely stay again!"
United States
Sara A.
The price is HK$588
HK$1,403 total
includes taxes & fees
18 Oct - 19 Oct
Luxury Downtown Apt with Parking, Gym, and Lap Pool · Sleeps 4-5
A modern living room with a sofa, armchair, and a TV.

3. Westown Studio Apt Near Fiserv, Baird, and Theater District

Westown Studio Apt Near Fiserv, Baird, and Theater District
Westown
9.6 out of 10, Exceptional, (5 reviews)
"This was a perfect location for a work conference in Downtown Milwaukee. Most everything I needed was within walking distance. The space was clean and welcoming, with a great view."
United States
Jess
The price is HK$431
HK$997 total
includes taxes & fees
12 Oct - 13 Oct
Westown Studio Apt Near Fiserv, Baird, and Theater District
A modern kitchen with a large island, dark cabinetry, stainless steel appliances, and a city view through large windows.

4. Modern Luxury 1BR Apt with Rooftop, Gym, and Parking

Modern Luxury 1BR Apt with Rooftop, Gym, and Parking
Westown
9.4 out of 10, Exceptional, (31 reviews)
"Beautiful view, bright and clean, great location "
Canada
Breanna
The price is HK$468
HK$1,176 total
includes taxes & fees
2 Nov - 3 Nov
Modern Luxury 1BR Apt with Rooftop, Gym, and Parking
A room with a large window overlooking a city street, a brown leather sofa, and a small wooden table.

5. Deer District Studio Apt - One Block from Fiserv and Baird

Deer District Studio Apt - One Block from Fiserv and Baird
Westown
9.6 out of 10, Exceptional, (7 reviews)
"I was in town for a conference at Baird Center. It was perfect location and a great place to stay for one to two people (couple). Will definitely book again if I come back."
Canada
William
The price is HK$450
HK$1,155 total
includes taxes & fees
2 Nov - 3 Nov
Deer District Studio Apt - One Block from Fiserv and Baird
A modern bedroom with a large bed, a desk, and a balcony with chairs.

6. Brady St Oasis - Walkable & Quiet Neighborhood + Private Balcony | Sleeps 5

Brady St Oasis - Walkable & Quiet Neighborhood + Private Balcony | Sleeps 5
Downtown Milwaukee
9.6 out of 10, Exceptional, (8 reviews)
"Great "
United States
Chelsea K.
The price is HK$413
HK$977 total
includes taxes & fees
12 Oct - 13 Oct
Brady St Oasis - Walkable & Quiet Neighborhood + Private Balcony | Sleeps 5
A modern kitchen with a central island, bar stools, and pendant lighting.

7. Downtown Luxe 2BR Loft Apt | Sleeps 8 | Walkable

Downtown Luxe 2BR Loft Apt | Sleeps 8 | Walkable
Downtown Milwaukee
10.0 out of 10, Exceptional, (6 reviews)
"Easy entry and check out. The unit has great light and open with high ceilings. The bed was comfortable- which is important for this tall body with a sensitive back. I highly recommend!"
United States
Marissa G.
The price is HK$505
HK$1,263 total
includes taxes & fees
12 Oct - 13 Oct
Downtown Luxe 2BR Loft Apt | Sleeps 8 | Walkable
A modern kitchen with a large island, built-in appliances, and ample natural light.

8. East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge | Sleeps 4

East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge | Sleeps 4
Downtown Milwaukee
10.0 out of 10, Exceptional, (3 reviews)
"We enjoyed our stay at East Side Luxury apartments. Everything was as advertised and it was great staying close to Brady St. We would definitely stay here again."
United States
Greg W.
The price is HK$546
HK$1,130 total
includes taxes & fees
15 Oct - 16 Oct
East Side Luxury 1BR Apt - Near Brady St with Balcony and Lounge | Sleeps 4
A spacious indoor area with a high ceiling, metal beams, and a central seating area with sofas.

9. Cream City Industrial Loft Near Fiserv with Parking | Suite 4 | Sleeps 8

Cream City Industrial Loft Near Fiserv with Parking | Suite 4 | Sleeps 8
Westown
9.4 out of 10, Exceptional, (6 reviews)
"Great location & would stay again next in town!"
United States
Mary W.
The price is HK$422
HK$1,122 total
includes taxes & fees
12 Oct - 13 Oct
Cream City Industrial Loft Near Fiserv with Parking | Suite 4 | Sleeps 8
A modern living room with leather sofas, a round coffee table, and a large potted plant.

10. Third Ward Apt Near Summerfest with Gym and Balcony | Sleeps 4

Third Ward Apt Near Summerfest with Gym and Balcony | Sleeps 4
Downtown Milwaukee
8.4 out of 10, Very good, (6 reviews)
"Well located and convenient. Great communication! Relaxing and easy!"
United States
Tanya
The price is HK$439
HK$1,007 total
includes taxes & fees
9 Nov - 10 Nov
Third Ward Apt Near Summerfest with Gym and Balcony | Sleeps 4
A hotel room with a bed, a sofa, a chair, a TV, a desk, and a balcony with a view of buildings.

11. Walker`s Point Designer 2BR · Prime Location with Balcony and Gym · Sleeps 6

Walker`s Point Designer 2BR · Prime Location with Balcony and Gym · Sleeps 6
Fifth Ward
10.0 out of 10, Exceptional, (7 reviews)
"Great space! Clean and up to date. We got lucky and found a parking spot right in front sometime around 4:15pm. Instructions were clear on how to get in. Getting an Uber was fast and easy in the area. We plan to return next year to this same listing. Very happy we tried this out when we normally stay at a hotel. Highly recommend."
United States
Jennifer
The price is HK$554
HK$1,319 total
includes taxes & fees
9 Nov - 10 Nov
Walker`s Point Designer 2BR · Prime Location with Balcony and Gym · Sleeps 6
A living room with a sofa, a coffee table, a fireplace, a TV, and a bar area with a chair.

12. Cozy Modern Apartment w/ Parking – Close to Downtown

Cozy Modern Apartment w/ Parking – Close to Downtown
Marquette
8.8 out of 10, Excellent, (3 reviews)
"Very cozy, gave me homie vibes."
United States
Mireya
The price is HK$855
HK$1,425 total
includes taxes & fees
28 Oct - 29 Oct
Cozy Modern Apartment w/ Parking – Close to Downtown
A wooden structure with a black latch, partially covered in snow, against a brick wall.

13. Spacious Studio near Brady St

Spacious Studio near Brady St
Lower East Side
10.0 out of 10, Exceptional, (1 review)
"It was fine"
United States
M E.
The price is HK$466
HK$1,587 total
includes taxes & fees
3 Nov - 4 Nov
Spacious Studio near Brady St
A modern kitchen with a central island, stainless steel appliances, and bar stools.

14. Bay View Designer 1BR · Best Location with Balcony, Gym, and Terrace · Sleeps 4

Bay View Designer 1BR · Best Location with Balcony, Gym, and Terrace · Sleeps 4
Bay View
10.0 out of 10, Exceptional, (2 reviews)
"We adored this property. The area was great."
United States
Nicole W.
The price is HK$496
HK$1,117 total
includes taxes & fees
12 Oct - 13 Oct
Bay View Designer 1BR · Best Location with Balcony, Gym, and Terrace · Sleeps 4
A modern kitchen with white cabinets, a stainless steel stove, and a wooden countertop.

15. Remodeled Home - Steps from Brady Street!

Remodeled Home - Steps from Brady Street!
Downtown Milwaukee
10.0 out of 10, Exceptional, (12 reviews)
"Nice place, close to Brady Street."
United States
Kevin M.
The price is HK$541
HK$2,304 total
includes taxes & fees
19 Oct - 20 Oct
Remodeled Home - Steps from Brady Street!
A dining area with a round table, four chairs, a wooden floor, a door, and a lamp.

16. 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 bedroom with a bed, a desk, a chair, a lamp, a ceiling fan, and a window with a sign.

17. The Nohl | A Lake Effect Stay Near Brady Street

The Nohl | A Lake Effect Stay Near Brady Street
Lower East Side
The price is HK$659
HK$2,047 total
includes taxes & fees
12 Oct - 13 Oct
The Nohl | A Lake Effect Stay Near Brady Street
A spacious living room with a large window, a sofa, a coffee table, and a hanging plant.

18. Cozy 1BD w/ View in Walker's Point, Free Parking

Cozy 1BD w/ View in Walker's Point, Free Parking
Fifth Ward
10.0 out of 10, Exceptional, (19 reviews)
"Perfect stay. The apartment was clean, beautiful, and comfortable. We would stay there again. "
United States
Dena
The price is HK$1,154
HK$2,230 total
includes taxes & fees
13 Oct - 14 Oct
Cozy 1BD w/ View in Walker's Point, Free Parking
A modern hotel room with a large bed, a sofa, a desk, and a view of the beach.

19. Luxury Penthouse Apt Near Brady St with Balcony and Lake View

Luxury Penthouse Apt Near Brady St with Balcony and Lake View
Lower East Side
The price is HK$689
HK$1,294 total
includes taxes & fees
20 Oct - 21 Oct
Luxury Penthouse Apt Near Brady St with Balcony and Lake View
A bar area with a vintage cash register, a wooden counter, and a menu board.

20. Kegel`s Inn - Studio - Classic Apartment #3

Kegel`s Inn - Studio - Classic Apartment #3
West Allis
9.0 out of 10, Wonderful, (7 reviews)
"Great place"
Canada
Zachary
The price is HK$767
HK$1,473 total
includes taxes & fees
13 Oct - 14 Oct
Kegel`s Inn - Studio - Classic Apartment #3
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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Top Milwaukee Hotel Reviews

The Iron Horse Hotel

The Iron Horse Hotel

10/10 Excellent
"I had to check in early due to an upcoming event and the front desk staff person couldn’t have been more helpful. The room was perfect and fit the vibe of the hotel. The staff at the bar outside were attentive. I’ll definitely be back!"
Catherine 1-night trip
Posted 11 hours ago
The Iron Horse Hotel

Find out more about Milwaukee

Search for holiday rentals in Milwaukee on Expedia! You can easily find your home rentals, villas, holiday apartments in Milwaukee using one of the methods below:

  • View our selection of featured holiday rentals in Milwaukee
  • Use the map to find apartments and other holiday homes in the Milwaukee neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Milwaukee while they last

Look no further and take a look at our great range of rental properties in Milwaukee!

Frequently asked questions

Are there holiday rentals in Milwaukee?

Yes, there are holiday rentals in Milwaukee close to Marcus Performing Arts Center, or you can select a more secluded option if you're looking for a relaxing stay. Travellers who like culture and the arts give Milwaukee high marks for its acclaimed theatre scene and fascinating museums. The great live music and lively festivals are some other things you might like to check out during your trip.

What are some of the best holiday rentals that Milwaukee has to offer?

Three Bedroom Upper: This highly rated holiday home rental in Milwaukee is located near the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind. Some other top choices in Milwaukee are Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10 and Remodeled Luxury 3BR - Walk to Cedarburg Downtown.

How many holiday rentals are there in Milwaukee?

Choose from 545 Expedia holiday rentals in Milwaukee for a memorable holiday.

What can I see and do in Milwaukee?

Cultural attractions include Riverside Theater and Pabst Theater, whereas Lake Michigan and Cathedral Square are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Milwaukee City Hall and Milwaukee Repertory Theater.

What’s a holiday rental in Milwaukee like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Milwaukee. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.