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Discover Hillside hotels and places to stay, with room rates, reviews, and availability. Most hotels are fully refundable.

Lobby
The Pfister Hotel

The Pfister Hotel

4.5 star property
Downtown Milwaukee, 1.2 mi from Hillside
9.6 out of 10, Exceptional, (1785)
"Ive stayed here many times, never disappointed."
United States
WILLIAM NEIL
$169 nightly
The price is $199
Dec 25 - Dec 26
Total with taxes and fees
The Pfister Hotel
Exterior
Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

3.0 star property
Downtown Milwaukee, 1.2 mi from Hillside
9.6 out of 10, Exceptional, (1999)
" Loved our stay!!"
United States
Morgan
$100 nightly
The price is $118
Jan 1 - Jan 2, 2026
Total with taxes and fees
Drury Plaza Hotel Milwaukee Downtown
The Parlor | Premium bedding, down comforters, in-room safe, blackout drapes
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4.0 star property
Downtown Milwaukee, 0.9 mi from Hillside
9.8 out of 10, Exceptional, (2450)
"Friendly staff, clean room, good food."
United States
Nathan
$148 nightly
The price is $174
Dec 28 - Dec 29
Total with taxes and fees
Saint Kate - The Arts Hotel
Front of property - evening/night
Hyatt Place Milwaukee/Downtown

Hyatt Place Milwaukee/Downtown

3.0 star property
Westown, 0.5 mi from Hillside
9.4 out of 10, Exceptional, (1001)
"Staff is awesome and the rooms are clean. "
United States
Maria Concepcion
$113 nightly
The price is $133
Dec 8 - Dec 9
Total with taxes and fees
Hyatt Place Milwaukee/Downtown
Exterior
DoubleTree by Hilton Milwaukee Downtown

DoubleTree by Hilton Milwaukee Downtown

4.0 star property
Westown, 1 mi from Hillside
9.2 out of 10, Wonderful, (1001)
"Staff are super friendly & accommodating!"
United States
MAUREEN
$89 nightly
The price is $105
Dec 11 - Dec 12
Total with taxes and fees
DoubleTree by Hilton Milwaukee Downtown
Exterior
Tru By Hilton Milwaukee Downtown, WI

Tru By Hilton Milwaukee Downtown, WI

2.5 star property
Downtown Milwaukee, 1.4 mi from Hillside
8.2 out of 10, Very Good, (1000)
"Room, staff, amenities, breakfast, parking was spot on! "
United States
Donni Lai Ying
$79 nightly
The price is $93
Dec 21 - Dec 22
Total with taxes and fees
Tru By Hilton Milwaukee Downtown, WI
Indoor pool
Aloft Milwaukee Downtown

Aloft Milwaukee Downtown

3.0 star property
Westown, 0.6 mi from Hillside
8.6 out of 10, Excellent, (1004)
"Great location and amenities for the price. "
United States
Nichole
$93 nightly
The price is $109
Dec 14 - Dec 15
Total with taxes and fees
Aloft Milwaukee Downtown
Front of property - evening/night
Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

4.0 star property
Westown, 0.9 mi from Hillside
8.4 out of 10, Very Good, (1209)
"Great hotel. Ideal location "
United States
Roger
$93 nightly
The price is $109
Dec 7 - Dec 8
Total with taxes and fees
Hyatt Regency Milwaukee
3 restaurants, breakfast, lunch, dinner served; American cuisine
The Trade, Autograph Collection

The Trade, Autograph Collection

4.0 star property
Westown, 0.5 mi from Hillside
9.4 out of 10, Exceptional, (502)
"Clean room, and great front desk staff."
United States
Jason
$139 nightly
The price is $164
Dec 21 - Dec 22
Total with taxes and fees
The Trade, Autograph Collection
Exterior
The Westin Milwaukee

The Westin Milwaukee

4.0 star property
Downtown Milwaukee, 1.5 mi from Hillside
9.0 out of 10, Wonderful, (845)
"Clean room, great staff"
United States
Steven
$127 nightly
The price is $149
Dec 19 - Dec 20
Total with taxes and fees
The Westin Milwaukee
Exterior
Marriott Milwaukee Downtown

Marriott Milwaukee Downtown

4.0 star property
Downtown Milwaukee, 1.2 mi from Hillside
9.2 out of 10, Wonderful, (703)
"Excellent location "
United States
Thomas
$119 nightly
The price is $141
Dec 21 - Dec 22
Total with taxes and fees
Marriott Milwaukee Downtown
Hallway
The Iron Horse Hotel

The Iron Horse Hotel

4.0 star property
Fifth Ward, 1.8 mi from Hillside
9.2 out of 10, Wonderful, (1003)
"Great place to stay! "
United States
Donna
$129 nightly
The price is $152
Dec 24 - Dec 25
Total with taxes and fees
The Iron Horse Hotel
Exterior
The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 star property
Westown, 0.5 mi from Hillside
9.4 out of 10, Exceptional, (1024)
"Enjoy the stay very much"
United States
Gabriel
$127 nightly
The price is $149
Dec 14 - Dec 15
Total with taxes and fees
The Brewhouse Inn & Suites
Exterior
Courtyard by Marriott Milwaukee Downtown

Courtyard by Marriott Milwaukee Downtown

3.0 star property
Westown, 1.1 mi from Hillside
8.8 out of 10, Excellent, (1003)
"Friendly staff, clean room"
United States
Derek
$101 nightly
The price is $119
Dec 21 - Dec 22
Total with taxes and fees
Courtyard by Marriott Milwaukee Downtown
Interior entrance
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

4.0 star property
Marquette, 1.4 mi from Hillside
9.0 out of 10, Wonderful, (1252)
"Wonderful time Wonderful place"
United States
Darrin
$71 nightly
The price is $83
Dec 21 - Dec 22
Total with taxes and fees
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham
Property amenity
Holiday Inn Express & Suites Milwaukee - Brookfield by IHG

Holiday Inn Express & Suites Milwaukee - Brookfield by IHG

2.5 star property
10.7 mi from Hillside
9.4 out of 10, Exceptional, (901)
"Staff was awesome and the room was great too! Would highly recommend!! "
United States
Janice
$91 nightly
The price is $105
Jan 1 - Jan 2, 2026
Total with taxes and fees
Holiday Inn Express & Suites Milwaukee - Brookfield by IHG
Free daily buffet breakfast
SpringHill Suites by Marriott Milwaukee Downtown

SpringHill Suites by Marriott Milwaukee Downtown

3.0 star property
Westown, 0.9 mi from Hillside
9.0 out of 10, Wonderful, (1001)
"Room was clean and staff was attentive and welcoming! "
United States
Flor
$93 nightly
The price is $109
Dec 14 - Dec 15
Total with taxes and fees
SpringHill Suites by Marriott Milwaukee Downtown
Breakfast, lunch, dinner served; local and international cuisine
Renaissance Milwaukee West Hotel

Renaissance Milwaukee West Hotel

4.0 star property
Wauwatosa, 6.3 mi from Hillside
9.0 out of 10, Wonderful, (826)
"Quite....safe...excellent accommodations...nearby shopping and dining "
United States
Willie
$126 nightly
The price is $146
Dec 14 - Dec 15
Total with taxes and fees
Renaissance Milwaukee West Hotel
Indoor pool
Hyatt Place Milwaukee Airport

Hyatt Place Milwaukee Airport

3.0 star property
7.3 mi from Hillside
8.8 out of 10, Excellent, (1227)
"Very good for what it is - namely an airport hotel. I would stay there again."
United States
Karl
$88 nightly
The price is $104
Dec 8 - Dec 9
Total with taxes and fees
Hyatt Place Milwaukee Airport
Terrace/patio
Kimpton Journeyman Hotel by IHG

Kimpton Journeyman Hotel by IHG

4.5 star property
Historic Third Ward, 1.6 mi from Hillside
9.4 out of 10, Exceptional, (930)
"We had a great time here. It is walkable to many great places. The rooftop bar is fun."
United States
Michael
$155 nightly
The price is $183
Dec 29 - Dec 30
Total with taxes and fees
Kimpton Journeyman Hotel by IHG
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

Top Hillside Hotel Reviews

The Iron Horse Hotel

The Iron Horse Hotel

10/10 Excellent
"Walking in the place has a real warm feel. The folks that greeted me at the front desk were genuine, warm, and very kind. You can tell they love their work place. Customer Service was amazing!!! I had my dog and they had so many wonderful amenities for her from bowls, treats, a name board, a plush squeaky toy, and best of all a pink bandana! Spoiled rotten as was I. The food was good. The room was very clean and decorated beautifully. I loved the two days I stayed there and highly recommend it!"
Mary 1-night trip
Posted 11 hours ago
The Iron Horse Hotel

Frequently asked questions

What is Hillside like?
Travelers will be sure to enjoy their time in Milwaukee's Hillside neighborhood.
If I need to cancel my hotel reservation in Hillside, will I receive a refund?
Yes, most room reservations are fully refundable provided that you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you have a reservation that's non-refundable, you might be able to cancel it and be given a refund within 24 hours of booking. Plug in your dates, click on "Search", then use the "fully refundable" filter to review the best deals in Hillside.
Where can I learn more about changing or cancelling my trip to Hillside?
For additional details about rescheduling or cancelling your trip to Hillside, head over to our customer service page.
What are the top things to see and do in Hillside?
A few places to visit in the area around Hillside include Milwaukee Youth Arts Center, Best Place at the Historic Pabst Brewery, and Fiserv Forum. While you're out sightseeing, Turner Hall and the Milwaukee Turners and Miller High Life Theatre are a couple of additional sights to visit in Milwaukee.

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