Bayside Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Bayside Vacation
Lock in a Bayside vacation package and get set to experience all this city has to offer. Think about staying in the neighborhood of East Town, which is good for families, nightlife and dining. If a sightseeing tour is on the to-do list during your trip to Bayside, stop by popular attractions like Milwaukee River Walk, Concordia University Wisconsin and Rays MTB Indoor Mountain Bike Park. Whoever you're traveling with and whatever the size of your budget, your ultimate Bayside vacation is just a few clicks away with Expedia.
Top Bayside Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Kinn Guesthouse Bay View
Bay View
Price was CA $1,298, price is now CA $948 per person
CA $948
per person
Mar 26 - Mar 31
found 2 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9.6/10 Exceptional! (428 reviews)
The room was great, location was perfect. I loved the loft vibe and exposed brick. It would have been a 5 star review if the TV was working. We couldn't get the TV to turn on.
Reviewed on Nov 5, 2025
The Iron Horse Hotel
Fifth Ward
Price was CA $1,721, price is now CA $1,236 per person
CA $1,236
per person
Mar 26 - Mar 31
found 2 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9.2/10 Wonderful! (1,008 reviews)
Check in with Deb was not good-she was rude and didn’t offer an upgrade when we asked as Expedia Gold members. Met Shy later at desk-very nice and bartenders and breakfast server nice. Valet attendants also good. Very warm in gym and no water or hand sanitizer available.
Reviewed on Feb 1, 2026
Holiday Inn Express Milwaukee Downtown by IHG
Downtown Milwaukee
Price was CA $1,424, price is now CA $1,038 per person
CA $1,038
per person
Mar 26 - Mar 31
found 2 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9/10 Wonderful! (1,002 reviews)
Room was good for the price however housecleaning was hit or miss and they did not clean the bathroom floor once in the 5 days we were there and on the days they did clean the room, they would forget to empty out the trash cans or left the bathroom sink dirty. Breakfast was just ok, nothing to rave about. The staff day staff was much more helpful than the night staff but both were friendly. The hotel itself is nice and centrally located. We walked almost everywhere.
Reviewed on Jan 27, 2026
Potawatomi Hotel & Casino
Menomonee River Valley
Price was CA $1,399, price is now CA $1,033 per person
CA $1,033
per person
Mar 26 - Mar 31
found 2 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9/10 Wonderful! (1,357 reviews)
Room was clean and beautiful!! Front desk staff was helpful and has one of the best selections of slot machines in the casino will definitely be going back!!!
Reviewed on Feb 7, 2026
The Brewhouse Inn & Suites
Westown
Price was CA $1,747, price is now CA $1,315 per person
CA $1,315
per person
Mar 26 - Mar 31
found 2 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9.4/10 Exceptional! (1,001 reviews)
The room was cute, the staff was amazing, and the restaurant was top notch!
Reviewed on Feb 5, 2026
Bayside Hotel Deals
The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Mar 1 to Mar 2
CA $172
CA $203 total
Mar 1 - Mar 2
includes taxes & fees
9.4/10 Exceptional! (1,936 reviews)
Yes, the room was spotless. The staff members went out of their way to make us feel welcome.
Reviewed on Feb 6, 2026
Saint Kate - The Arts Hotel
139 E Kilbourn Ave Milwaukee WI
The price is CA $165 per night from Feb 22 to Feb 23
CA $165
CA $195 total
Feb 22 - Feb 23
includes taxes & fees
9.6/10 Exceptional! (2,550 reviews)
Everything about our stay deserves 5 Stars....from the moment we walked in to the moment we left and everything in between. The staff people we interacted with were nothing short of pleasant & eager to help, the room was not only comfortable, but fun & unique and the art galleries added a special ...
Reviewed on Feb 6, 2026
Drury Plaza Hotel Milwaukee Downtown
700 N. Water Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Feb 12 to Feb 13
CA $137
CA $161 total
Feb 12 - Feb 13
includes taxes & fees
9.6/10 Exceptional! (2,042 reviews)
GREAT HOTEL. You can tell its family owned. Clean. Luxury. The amenities are above and beyond....for instance the complimentary happy hour and light food bites...more like a meal. Staff was super friendly and knowledgeable. After our stay we looked at their other locations so we can be sure to stay ...
Reviewed on Feb 6, 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 Bayside
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.
What to do in Bayside
Milwaukee Scavenger Hunt Walking Tour and Game
CA $67
per adult
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
