Hillside Vacation Packages

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Top Holiday Package Deals in Hillside

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Milwaukee - Brookfield
Kinn Guesthouse Bay View
The Brewhouse Inn & Suites
SpringHill Suites by Marriott Milwaukee West/Wauwatosa
Wildwood Lodge

Where to stay in Hillside

Find the best Hillside areas and neighborhoods for the activities you enjoy most. Learn more about Hillside

Hillside Hotel Deals

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 CA $261 per night from Sep 21 to Sep 22
CA $261
CA $308 total
Sep 21 - Sep 22
includes taxes & fees
9.4/10 Exceptional! (1,727 reviews)
"Excellent hotel."

Reviewed on Sep. 9, 2025

The Pfister Hotel
Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

3 out of 5
700 N. Water Street, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is CA $177 per night from Sep 21 to Sep 22
CA $177
CA $208 total
Sep 21 - Sep 22
includes taxes & fees
9.6/10 Exceptional! (1,879 reviews)
"Absolutly love the 530 kickback! And the breakfast buffet, something for everyone! Rooms very nice, clean, spacious and comfy! Great amenities in the rooms. Pool isnt to cold, and the hot tub is fantastic! Very nice and hot like a hot tub should be, and the jets work great as well. Staff are pleasant ..."

Reviewed on Sep. 9, 2025

Drury Plaza Hotel Milwaukee Downtown
Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
1611 West Canal Street, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from Sep 22 to Sep 23
CA $204
CA $240 total
Sep 22 - Sep 23
includes taxes & fees
9/10 Wonderful! (1,343 reviews)
"Nice room. Good stay."

Reviewed on Sep. 10, 2025

Potawatomi Hotel & Casino
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

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.