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
Price was CA $1,104, price is now CA $826 per person
CA $826
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
8.4/10 Very Good! (1,004 reviews)
It was a wonderful experience. The staff was super friendly and kind. We found it kid friendly and felt safe.
Reviewed on Aug 15, 2025
Kinn Guesthouse Bay View
Bay View
Price was CA $1,302, price is now CA $937 per person
CA $937
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.6/10 Exceptional! (410 reviews)
The house was spacious and well equipped the downstairs restaurant was great. The stairs up to the guest rooms were reminiscent of Europe where elevators are scarce
Reviewed on Sep 10, 2025
The Brewhouse Inn & Suites
Westown
Price was CA $1,594, price is now CA $1,183 per person
CA $1,183
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.4/10 Exceptional! (1,025 reviews)
A wonderful experience, for travelers seeking an authentic experience...rooms are dated, but clean. Staff super friendly accommodating .... Bar onsite is wonderful with good food.
Reviewed on Sep 13, 2025
SpringHill Suites by Marriott Milwaukee West/Wauwatosa
Wauwatosa
Price was CA $1,291, price is now CA $971 per person
CA $971
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.2/10 Wonderful! (688 reviews)
They really need a restaurant. The breakfast adequate, quick, hot and two or three hot options, but I go there for business and after a long day I have to order in dinner and eat a cold meal in my room. The closest restaurant closes at 4pm. Without a rental car there’s no where to walk to. Even soup and sandwiches prepared off site and sold between 6 and 10 would be an improvement. Staff is friendly, hotel is quiet rooms are clean and well appointed.
Reviewed on Aug 29, 2025
Wildwood Lodge
Price was CA $1,168, price is now CA $891 per person
CA $891
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
8.4/10 Very Good! (1,009 reviews)
The friendly staff is what makes this place such a gem. You’ll feel right at home. The rooms are very arranged well. nice couch area so you aren’t confined to your bed. microwave, nice size mini fridge and coffee maker are also nice touches that are becoming hard to find in hotels these days. Very clean and comfy beds too! Nice quiet location. Only con is no elevator. but there are only 3 floors so it’s really not a big deal. Did i mention a free beer at check in? Noice.
Reviewed on Sep 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
The Pfister Hotel
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
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 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
Potawatomi Hotel & Casino
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
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
Brew City Ghosts: Macabre Milwaukee By US Ghost Adventures
CA $44
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.
