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Milwaukee County Holiday Rentals

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Featured Milwaukee County Holiday Rentals

Iron/ironing board, free WiFi, bed sheets
The Plaza Hotel

The Plaza Hotel

3.0 star property
Downtown Milwaukee
8.8 out of 10, Excellent, (1153)
"Loved this hotel! Clean friendly and cute!!"
United States
Sharon H
The price is HK$1,120
HK$1,320 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Plaza Hotel
Fireplace
Kasa Westown Milwaukee

Kasa Westown Milwaukee

4.0 star property
Westown
9.0 out of 10, Wonderful, (118)
"Hosts get 5 stars for excellent communication. They checked in with me multiple times on my day of arrival to make sure everything was good and they gave very thorough instructions."
United States
Melissa
Kasa Westown Milwaukee
Billiards
ROVE LIVING/KL - Malt House

ROVE LIVING/KL - Malt House

4.0 star property
Westown
8.8 out of 10, Excellent, (10)
"Loved the uniqueness, location and cleanliness of the unit."
United States
Teresa
The price is HK$452
HK$1,280 total
includes taxes & fees
9 Dec - 10 Dec
ROVE LIVING/KL - Malt House
Dining room
ROVE LIVING/KB - Prospect

ROVE LIVING/KB - Prospect

3.0 star property
Lower East Side
7.6 out of 10, Good, (7)
"Our stay was great. The property was at it was described and expected. The owner was available via text and communicated with me when I had questions. We would stay again!"
United States
Vera
ROVE LIVING/KB - Prospect
Exterior
Downtown Eastside gem near Fiserv Forum Water St Brady St

Downtown Eastside gem near Fiserv Forum Water St Brady St

Downtown Milwaukee
9.0 out of 10, Wonderful, (46)
"The check in instructions were perfect and not sure he could have laid that out any better. It's a nice place close to everything. We'd stay there again. "
United States
Chad-Tara A.
The price is HK$1,752
HK$2,588 total
includes taxes & fees
9 Dec - 10 Dec
Downtown Eastside gem near Fiserv Forum Water St Brady St
Dining
Three bedrooms upstairs

Three bedrooms upstairs

Riverwest
9.6 out of 10, Exceptional, (77)
"He was very kind!"
United States
Hope
The price is HK$1,366
HK$1,822 total
includes taxes & fees
15 Dec - 16 Dec
Three bedrooms upstairs
Dining
Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers

Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers

Bay View
9.6 out of 10, Exceptional, (8)
"Great place!"
United States
Kathy R.
The price is HK$1,853
HK$3,607 total
includes taxes & fees
15 Dec - 16 Dec
Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers
Fridge, microwave, oven, stovetop
Stunning Upscale Retreat - Steps From Everything

Stunning Upscale Retreat - Steps From Everything

Lower East Side
9.8 out of 10, Exceptional, (31)
"It was a great place and close to Brady street! Definitely recommend. "
United States
Hugh L.
The price is HK$1,576
HK$4,199 total
includes taxes & fees
9 Dec - 10 Dec
Stunning Upscale Retreat - Steps From Everything
Outdoor dining
MKE Mansion - Both Wings

MKE Mansion - Both Wings

Downtown Milwaukee
9.6 out of 10, Exceptional, (23)
"Great house - big group I stayed with loved it and tons of places to sleep and hang out. Fantastic location by the water and near some good restaurants. Hosts were super responsive. "
United States
Henri E.
The price is HK$7,777
HK$13,024 total
includes taxes & fees
4 Jan - 5 Jan 2026
MKE Mansion - Both Wings
Exterior
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

Johnson Woods
9.8 out of 10, Exceptional, (26)
"We stayed while attending the WI state fair. Quiet and safe neighborhood and really close to the fairgrounds. House was clean and easy to get to. We enjoyed our stay and the fenced in backyard was perfect for our Frenchie. "
United States
Roy W.
The price is HK$1,238
HK$2,597 total
includes taxes & fees
9 Dec - 10 Dec
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!
Dining
Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10

Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10

Burnham Park
9.6 out of 10, Exceptional, (252)
"This spacious house is a true gem, lovingly preserved. Really enjoyed our stay!!!!"
United States
Lynne W.
Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10
Interior
Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!

Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!

River Hills
8.0 out of 10, Very good, (4)
"Love the indoor pool and the movie room!"
United States
JOE C.
Spacious 5-bedroom house in awesome River Hills with an INDOOR POOL!
Interior
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms

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

2.0 star property
Lower East Side
9.8 out of 10, Exceptional, (19)
"Great property for our family group for a long weekend in Milwaukee. "
United States
Karl S.
The price is HK$1,023
HK$3,280 total
includes taxes & fees
16 Dec - 17 Dec
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms
Fridge, microwave, oven, stovetop
Remodeled Home - Steps from Brady Street!

Remodeled Home - Steps from Brady Street!

Downtown Milwaukee
10.0 out of 10, Exceptional, (5)
"Enjoyed stay at this nice home "
United States
Eduardo P.
The price is HK$381
HK$2,083 total
includes taxes & fees
9 Dec - 10 Dec
Remodeled Home - Steps from Brady Street!
Property grounds
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
9.6 out of 10, Exceptional, (66)
"Dustin was a great host! Very easy to communicate with and the house was great as well, thanks much!"
United States
Lisa M.
The price is HK$1,415
HK$3,257 total
includes taxes & fees
9 Dec - 10 Dec
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
Interior
Cozy 2 Bedroom Downtown Milwaukee Apartment

Cozy 2 Bedroom Downtown Milwaukee Apartment

Downtown Milwaukee
9.8 out of 10, Exceptional, (13)
"Great little upper apartment. Had everything we needed. You could not beat the location for access to the lake, veterans Park, and downtown."
United States
NE B.
Cozy 2 Bedroom Downtown Milwaukee Apartment
Outdoor dining
Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer

Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer

2.0 star property
Bay View
10.0 out of 10, Exceptional, (26)
"Very comfortable and convenient to everything downtown."
United States
Reddemann R.
The price is HK$1,121
HK$3,084 total
includes taxes & fees
15 Dec - 16 Dec
Charming Bungalow / ❤️ of Bay View / Parking - Central Air - Deck - Washer/Dryer
Fridge, microwave, oven, stovetop
Style and Luxury - Unbeatable Location

Style and Luxury - Unbeatable Location

Lower East Side
9.6 out of 10, Exceptional, (13)
"Great location!"
United States
Mike G.
The price is HK$1,717
HK$4,126 total
includes taxes & fees
9 Dec - 10 Dec
Style and Luxury - Unbeatable Location
Fridge, microwave, stovetop, dishwasher
Deluxe Dwelling 4Br, 2Ba| Sunlit, Spacious, Serine

Deluxe Dwelling 4Br, 2Ba| Sunlit, Spacious, Serine

Downtown Milwaukee
9.8 out of 10, Exceptional, (19)
"Great neighborhood to stay. "
United States
Alex N.
The price is HK$2,203
HK$4,329 total
includes taxes & fees
12 Dec - 13 Dec
Deluxe Dwelling 4Br, 2Ba| Sunlit, Spacious, Serine
Fridge, microwave, oven, stovetop
Renovated Brady St. Classic

Renovated Brady St. Classic

Downtown Milwaukee
8.4 out of 10, Very good, (10)
"Comfortable property in a great location. Liked that my adult children could walk to nearby restaurants, shops and bars. Neighborhood parking is limited, but not unusual for downtown-type stays."
United States
Mike F.
Renovated Brady St. Classic
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 County Hotel Reviews

Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

10/10 Excellent
"The room was spotless. The shower was wonderful. We got hot water right away and plenty of towels. Amenities were readily available. The hot breakfast and the kickback at 5:30pm were also a wonderful addition to the stay. The food was delicious and the service was also great. Everything was also within walking distance and very convenient . We intend on coming back for a return visit in the future. "
Gail 3-night trip
Posted 3 days ago
Drury Plaza Hotel Milwaukee Downtown