Hillside
Milwaukee
Visit Hillside
Things to do
Small Group Kayak Tour of Skyline in Milwaukee
CA $115
per adult
Haunting Histories: An Audio Tour of Milwaukee‘s Wicked Westown
CA $12
per adult
City of Neighborhoods: A Self-Guided Audio Tour in Milwaukee
CA $11
per adult
Hillside Hotel Deals
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
The price is CA $272 per night from Oct 4 to Oct 5
CA $272
CA $321 total
Oct 4 - Oct 5
includes taxes & fees
Book a stay at this luxury hotel in Milwaukee. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
9.6/10 Exceptional! (2,274 reviews)
"Clean, quiet, and convenient. Great to stay in a historic hotel that is so well maintained and used. The only flaw, the service in the hotel steak house was slow and inattentive. We sat for hours in the dinning area."
Reviewed on Sep 20, 2026
Hyatt Regency Milwaukee
333 W Kilbourn Ave Milwaukee WI
The price is CA $130 per night from Sep 29 to Sep 30
CA $130
CA $153 total
Sep 29 - Sep 30
includes taxes & fees
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,471 reviews)
"excellernts property"
Reviewed on Sep 19, 2026
AmericInn by Wyndham Brookfield
16865 W Bluemound Rd Brookfield WI
The price is CA $110 per night from Sep 27 to Sep 28
CA $110
CA $127 total
Sep 27 - Sep 28
includes taxes & fees
Book a stay at this business-friendly hotel in Brookfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very good! (1,609 reviews)
"The bed sheets were dirty."
Reviewed on Sep 20, 2026
Drury Plaza Hotel Milwaukee Downtown
700 N. Water Street Milwaukee WI
The price is CA $179 per night from Sep 29 to Sep 30
CA $179
CA $211 total
Sep 29 - Sep 30
includes taxes & fees
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
9.6/10 Exceptional! (2,384 reviews)
"We had a great stay. The bed was very comfortable and the breakfast was fantastic. We would definitely stay here again."
Reviewed on Sep 20, 2026
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham
2308 W Wisconsin Ave Milwaukee WI
The price is CA $117 per night from Oct 6 to Oct 7
CA $117
CA $137 total
Oct 6 - Oct 7
includes taxes & fees
Stay at this hotel in Milwaukee. Enjoy 2 restaurants, breakfast (surcharge), and a free area shuttle. Our guests praise the bar and the helpful staff in our ...
9/10 Wonderful! (1,392 reviews)
"Friendly staff food is great and hospitality"
Reviewed on Sep 20, 2026
The Iron Horse Hotel
500 W Florida Street Milwaukee WI
The price is CA $254 per night from Oct 11 to Oct 12
CA $254
CA $299 total
Oct 11 - Oct 12
includes taxes & fees
Book a stay at this boutique hotel in Milwaukee. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,336 reviews)
"Amazing food in the outdoor bar area we had lunch and dinner there and both meals were excellent also wait staff were great and super attentive we highly recommend eating there."
Reviewed on Sep 19, 2026
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.
Where to stay in Hillside
Find the best Hillside areas and neighborhoods for the activities you enjoy most. Learn more about Hillside
Learn more about Hillside
Downtown Milwaukee
Known for its fantastic nightlife, stunning river views, and acclaimed art galleries, there's plenty to explore in Downtown Milwaukee. Top attractions like Lake Michigan and Pabst Theater are major draws. Catch the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop to see more of the city.
Wauwatosa
Wauwatosa is known for its abundant dining options, and you can plan a trip to Mayfair Mall and The Mayfair Collection while you're in town.
West Allis
West Allis is noteworthy for its restaurants, and you can make a stop at top attractions like Milwaukee Mile Speedway and Wisconsin State Fair Park.
Historic Third Ward
Unique features of Historic Third Ward include the bars and shopping. Make a stop by Lake Michigan or Milwaukee Public Market while you're exploring the area.
East Town
East Town is highly notable for its fantastic nightlife, and you might want to visit top sights like Lake Michigan and Veteran's Park. See more of Milwaukee by jumping on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop.
Hillside
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