Hillside Vacation Packages
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Top Holiday Package Deals in Hillside
Price found within the past 48 hours. Click for updated prices.
Abbey Resort and Avani Spa
Price was CA $835, price is now CA $662 per person
CA $662
per person
Oct 24 - Oct 28
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Milwaukee (MKE)
8.6/10 Excellent! (1,429 reviews)
Bathroom was not cleaned properly. Hair on floor and around the bottom of toilet. Hallways have no ventilation (warm and musty). Room carpet needs a refresh.
Reviewed on Aug. 19, 2025
The Brewhouse Inn & Suites
Westown
Price was CA $1,279, price is now CA $1,110 per person
CA $1,110
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.4/10 Exceptional! (1,012 reviews)
The hotel was very historic and the rooms were large, well appointed and quiet.
Reviewed on Aug. 19, 2025
Kinn Guesthouse Bay View
Bay View
Price was CA $1,253, price is now CA $1,108 per person
CA $1,108
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.6/10 Exceptional! (402 reviews)
The beds are so comfortable and the decor is great! There is really no staff there to connect with, which is different. You go and leave like its an apartment- they just send codes and there is no service desk. I loved the place! Very steep stairs for older people to go up.
Reviewed on Aug. 10, 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
Sonesta Select Milwaukee Brookfield
16865 W Bluemound Rd, Brookfield, WI
Fully refundableReserve now, pay when you stay
The price is CA $120 per night from Aug 25 to Aug 26
CA $120
CA $139 total
Aug 25 - Aug 26
includes taxes & fees
8/10 Very Good! (1,255 reviews)
"Very nice weekend stay"
Reviewed on Aug. 18, 2025
Drury Plaza Hotel Milwaukee Downtown
700 N. Water Street, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Aug 27 to Aug 28
CA $176
CA $207 total
Aug 27 - Aug 28
includes taxes & fees
9.6/10 Exceptional! (1,842 reviews)
"Very nice property, easy parking!"
Reviewed on Aug. 19, 2025
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham
2308 W Wisconsin Ave, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from Aug 20 to Aug 21
CA $129
CA $152 total
Aug 20 - Aug 21
includes taxes & fees
8.8/10 Excellent! (1,148 reviews)
"Everyone was very nice and helpful."
Reviewed on Aug. 17, 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 Art Museum
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
Skip the Line: Museum Admission Ticket - Grohmann Museum
CA $7
per adult
The Grand Walk: A Self-Guided Audio Tour through Milwaukee
CA $12
per adult
80% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.