Hillside Holidays

Book a Hotel + Flight or Car together to unlock savings

Where to stay in Hillside

Find the best Hillside areas and neighborhoods for the activities you enjoy most. Learn more about Hillside
Downtown skyline with Buildings along the Milwaukee River, in Milwaukee, Wisconsin.; Shutterstock ID 523595590

Downtown Milwaukee

Lake Michigan and Pabst Theater are a few top attractions in Downtown Milwaukee. Hop around the city on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop and check out the area's fantastic nightlife, stunning river views and acclaimed art galleries.

Find hotels in Downtown Milwaukee

Top hotels in Hillside

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 3.943.964 ₫ per night from 22 Jan to 23 Jan
3.943.964 ₫
4.649.934 ₫ total
22 Jan - 23 Jan
includes taxes & fees
9.4/10 Exceptional! (1,872 reviews)
The Pfister exceeded my expectations. The staff was exceptional. The entire hotel sparkled.

Reviewed on 11 Jan 2026

The Pfister Hotel
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 4.174.581 ₫ per night from 24 Jan to 25 Jan
4.174.581 ₫
4.921.829 ₫ total
24 Jan - 25 Jan
includes taxes & fees
9.6/10 Exceptional! (2,515 reviews)
Great hotel! So fun and unique. Very clean and personalized

Reviewed on 11 Jan 2026

Saint Kate - The Arts Hotel
The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
500 W Florida Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is 3.760.239 ₫ per night from 29 Jan to 30 Jan
3.760.239 ₫
4.433.321 ₫ total
29 Jan - 30 Jan
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
Wonderful stay!

Reviewed on 9 Jan 2026

The Iron Horse Hotel
See all 1,112 properties in Hillside
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.

Popular places to visit

Outfield sign at miller park

American Family Field

Catch an event at American Family Field during your trip to Milwaukee. Attend a baseball game or simply enjoy the lively breweries while you're in the area.

American Family Field
Harley-Davidson Museum showing interior views

Harley-Davidson Museum

You can spend an afternoon browsing the exhibits at Harley-Davidson Museum in Milwaukee. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Harley-Davidson Museum
Downtown, Milwaukee

Marquette University

Explore the campus of Marquette University during your visit to Milwaukee. Attend a sporting event or simply enjoy the lively breweries while you're in the area.

Marquette University