Downtown Pewaukee Vacation Packages
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Top Holiday Package Deals in Downtown Pewaukee
Price found within the past 48 hours. Click for updated prices.
Sheraton Milwaukee Brookfield Hotel
Price was CA $1,205, price is now CA $1,041 per person
CA $1,041
per person
Jun 15 - Jun 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
8.4/10 Very Good! (738 reviews)
Our room was VERY loud by the elevators. Breakfast was expensive for the quality of food and only 2 GF options - fruit and bacon.
Reviewed on Apr 27, 2026
Kinn Guesthouse Bay View
Bay View
Price was CA $1,721, price is now CA $1,422 per person
CA $1,422
per person
Jun 15 - Jun 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.4/10 Exceptional! (459 reviews)
The room was very spacious and clean. We loved the convenience of the area and the many amenities es provided on site. The team did an amazing job of communicating with rapid speed.
Reviewed on Mar 23, 2026
Potawatomi Hotel & Casino
Menomonee River Valley
Price was CA $1,914, price is now CA $1,606 per person
CA $1,606
per person
Jun 15 - Jun 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.2/10 Wonderful! (1,431 reviews)
The room was so big and clean and the best bathroom I’ve ever stayed in
Reviewed on Apr 28, 2026
Homewood Suites by Hilton Wauwatosa Milwaukee
Wauwatosa
Price was CA $1,648, price is now CA $1,453 per person
CA $1,453
per person
Jun 15 - Jun 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
8.8/10 Excellent! (846 reviews)
Staff was friendly and helpful, breakfast hot and fresh. The evening mixer was very nice!
Reviewed on Apr 14, 2026
Where to stay in Downtown Pewaukee
Find the best Downtown Pewaukee areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Pewaukee
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.
Downtown Pewaukee 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 10 to May 11
CA $202
CA $239 total
May 10 - May 11
includes taxes & fees
9.2/10 Wonderful! (1,443 reviews)
Will stay here again!
Reviewed on Apr 28, 2026
The Iron Horse Hotel
500 W Florida Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Apr 30 to May 1
CA $163
CA $192 total
Apr 30 - May 1
includes taxes & fees
9.2/10 Wonderful! (1,083 reviews)
Great location near a bunch of good places. Very nice and clean rooms and there was tons of food options and bars connected to the hotel.
Reviewed on Apr 28, 2026
Drury Plaza Hotel Milwaukee Downtown
700 N. Water Street Milwaukee WI
The price is CA $178 per night from May 25 to May 26
CA $178
CA $210 total
May 25 - May 26
includes taxes & fees
9.6/10 Exceptional! (2,186 reviews)
Clean. Quiet. Check in was quick. Parking was ready. Drinks in the bar were great. The staff is awesome. Have stayed here several times and stay again!
Reviewed on Apr 27, 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 Downtown Pewaukee
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
Milwaukee,Harley-Davidson Museum, Miller Brewery 1-Day Trip from Chicago
CA $172
per traveller
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.