Hillside Vacations from $311
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The Latest Hillside Vacation Packages
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Milwaukee - Brookfield
Price was $455, price is now $311 per person
$311
per person
Feb 11 - Feb 15
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Milwaukee (MKE)
16.8/10 Exceptional! (1,001 reviews)
Clean room, most comfortable bed and pillows I’ve experienced in a hotel. There’s a bar and grill that offer food! Staff was very knowledgeable and pleasant.
Reviewed on Nov 17, 2025
Dubbel Dutch
Downtown Milwaukee
Save 100% on your flight
Price was $791, price is now $512 per person
$512
per person
Feb 11 - Feb 15
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Milwaukee (MKE)
18.4/10 Exceptional! (146 reviews)
There is a bar in the building that is loud until midnight. The parking fee was higher than the site warranted. The sofa couch was not suitable for any over 5' tall. It all depends on the room you get in terms of the experience. I would not stay there again, as it was more costly and had little to recommend it. No microwave in the room. Fridge froze my food overnight, making it useless and uneatable. NOT appropriate if you cannot walk up steps easily. I think a regular hotel room would have offered better service at a more reasonable price.
Reviewed on Oct 28, 2025
Holiday Inn Express Milwaukee Downtown by IHG
Downtown Milwaukee
Price was $634, price is now $424 per person
$424
per person
Feb 11 - Feb 15
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Milwaukee (MKE)
18/10 Exceptional! (1,002 reviews)
Le daría un 5 estrellas. Pero como es general le quito la estrella que falta por no tener el agua caliente de la ducha. Está tibia ni caliente. Recuerdan donde vivimos y el frío que hace para no tener un ma ducha caliente que darte. Por todo lo demás me encantó
Reviewed on Nov 14, 2025
Saint Kate - The Arts Hotel
Downtown Milwaukee
Price was $693, price is now $477 per person
$477
per person
Feb 11 - Feb 15
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Milwaukee (MKE)
19.6/10 Exceptional! (2,425 reviews)
What a beautiful hotel! And definitely a notch above the rest in hospitality.
Reviewed on Nov 17, 2025
Potawatomi Hotel & Casino
Menomonee River Valley
Save 100% on your flight
Price was $902, price is now $632 per person
$632
per person
Feb 11 - Feb 15
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Milwaukee (MKE)
18/10 Exceptional! (1,357 reviews)
Would definitely recommend
Reviewed on Nov 18, 2025
Where to stay in Hillside
Find the best Hillside areas and neighborhoods for the activities you enjoy most. Learn more about Hillside
Downtown Milwaukee
Central business district with cultural, financial, and historical landmarks, Downtown Milwaukee offers shopping at The Shops of Grand Avenue, art galleries in the Historic Third Ward, high-end dining, and vibrant nightlife. Explore the Milwaukee Public Market and Riverwalk, or hop on the free streetcar system.
Hillside Hotel Deals
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $140 total per night from Dec 10 to Dec 11
$140 total
Dec 10 - Dec 11
Total with taxes and fees
9.4/10 Exceptional! (1,782 reviews)
We had an amazing stay! The staff were warm and welcoming, the room was large and spotless, and the entire hotel felt luxurious. The lobby alone was breathtaking—truly an unforgettable experience!
Reviewed on Nov 17, 2025
Hilton Milwaukee
509 W Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $125 total per night from Dec 14 to Dec 15
$125 total
Dec 14 - Dec 15
Total with taxes and fees
8.2/10 Very Good! (1,079 reviews)
Clean room… friendly staff
Reviewed on Nov 18, 2025
Hyatt Regency Milwaukee
333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $109 total per night from Nov 23 to Nov 24
$109 total
Nov 23 - Nov 24
Total with taxes and fees
8.4/10 Very Good! (1,201 reviews)
The staff was really nice and helpful. The room was clean and it’s in a great location.
Reviewed on Nov 18, 2025
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.
Discover the most popular places to visit in Hillside
Harley-Davidson Museum
Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours.
Milwaukee County Zoo
This sprawling animal park houses a wide array of exotic wildlife, and is acclaimed for its conservation programs and educational resources.
Milwaukee Art Museum
Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.
Things to do
The Grand Walk: A Self-Guided Audio Tour through Milwaukee
$9
per adult
80% of travellers recommend
Milwaukee Best Street Food Tour With A Local Guide
$108
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.