Hillside Vacation Packages
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Top Holiday Package Deals in Hillside
Price found within the past 48 hours. Click for updated prices.
Kinn Guesthouse Bay View
Bay View
Price was CA $1,551, price is now CA $1,259 per person
CA $1,259
per person
Jul 2 - Jul 5
found 21 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Milwaukee (MKE)
9.4/10 Exceptional! (459 reviews)
Great place! Perfect myself and one child traveling for work.
Reviewed on May 1, 2026
Lake Lawn Resort
Price was CA $2,064, price is now CA $1,749 per person
CA $1,749
per person
Jun 24 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Milwaukee (MKE)
9.2/10 Wonderful! (1,008 reviews)
Beautiful resort. Gorgeous setting and rooms. Especially enjoyed 1878 restaurant and bar setting looking out over the lake. Observed outdoor wedding and indoor venues…lovely.
Reviewed on Apr 26, 2026
The Pfister Hotel
Downtown Milwaukee
Price was CA $2,115, price is now CA $1,496 per person
CA $1,496
per person
Jul 2 - Jul 5
found 21 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Milwaukee (MKE)
9.6/10 Exceptional! (2,080 reviews)
I had a wonderful stay at The Pfister Hotel. The hotel itself is beautiful, the accommodations were comfortable, and the overall service was excellent. I also had the opportunity to dine at the steakhouse, which was a great experience — the food and atmosphere were both outstanding. One of the highlights of the stay was the pool, which really stood out as a very nice amenity and added to the overall enjoyment of the weekend. I appreciated the hospitality and would gladly return for another stay.
Reviewed on May 7, 2026
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
Potawatomi Hotel & Casino
1611 West Canal Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $202 per night from May 11 to May 12
CA $202
CA $239 total
May 11 - May 12
includes taxes & fees
9.2/10 Wonderful! (1,457 reviews)
Great big rooms at a great price. Totally recommended.
Reviewed on May 7, 2026
The Iron Horse Hotel
500 W Florida Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $244 per night from May 28 to May 29
CA $244
CA $288 total
May 28 - May 29
includes taxes & fees
9.2/10 Wonderful! (1,101 reviews)
Nicely located and easy to get to
Reviewed on May 6, 2026
Drury Plaza Hotel Milwaukee Downtown
700 N. Water Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $177 per night from May 25 to May 26
CA $177
CA $209 total
May 25 - May 26
includes taxes & fees
9.6/10 Exceptional! (2,197 reviews)
Great stay! I knew we were getting a complimentary breakfast but I did not know we also got a complimentary dinner! Nice perks.
Reviewed on May 7, 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.
Discover the most popular places to visit in Hillside
Harley-Davidson Museum
5/5(13 reviews)
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 Art Museum
5/5(12 reviews)
Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.
Potawatomi Bingo Casino
Why not roll the dice with a visit to Potawatomi Bingo Casino during your time in Milwaukee? Attend a sporting event or simply enjoy the lively breweries while you're in the area.
Things to do
Small Group Kayak Tour of Skyline in Milwaukee
CA $114
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.