
Bayside Vacations from $568
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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.
The Latest Bayside vacation packages
Price found within the past 48 hours. Click for updated prices.

The Pfister Hotel
Downtown Milwaukee
Save 100% on your flight
Price was $947, price is now $568 per person
$568
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
9.6/10 Exceptional! (2,145 reviews)
Beautiful and wonderful staff
Reviewed on Jun 24, 2026

Saint Kate - The Arts Hotel
Downtown Milwaukee
Save 100% on your flight
Price was $865, price is now $604 per person
$604
per person
Jul 28 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
9.8/10 Exceptional! (2,669 reviews)
Honestly, one of the nicest cleanest hotels I ’ve ever stayed at. Everything was perfect !
Reviewed on Jun 25, 2026

Dubbel Dutch
Downtown Milwaukee
Save 100% on your flight
Price was $831, price is now $610 per person
$610
per person
Jul 28 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
9.2/10 Wonderful! (148 reviews)
The beds were incredibly comfortable.
I sat up with my friend talking for a couple hours, and we would’ve loved an ottoman between the two chairs to rest our feet on.
Reviewed on Jun 25, 2026

Kinn Guesthouse Bay View
Bay View
Save 100% on your flight
Price was $961, price is now $757 per person
$757
per person
Sep 8 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
9.4/10 Exceptional! (472 reviews)
We stayed in suite #8. It was beautiful and very roomy. It had all the amenities one could need and it was quiet and comfortable despite being right next to the hotel’s restaurant (which was delicious). There are just a few small things that needed tending to and the customer service response to help us with those were very quick. The #3 does not work on the inner keypad to enter the room and our code contained a 3. This has apparently been a problem for a little while. When we called, the gal gave us a new number right away. Also, there was no WiFi passcode in the room or in the communication prior to checkin. We had to call again for that. Service was wonderful again. The lights in the bathroom were partially out and there were no replacement bulbs in the room. We didn’t call about this but were hopeful the housekeepers would resolve the issue for the next guests. We will definitely stay again as these were very minor issues.
Reviewed on Jun 17, 2026

The Iron Horse Hotel
Fifth Ward
Price was $748, price is now $591 per person
$591
per person
Jul 28 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
9.2/10 Wonderful! (1,162 reviews)
Cool decor and hotel theme. Room was generous size. Helpful and friendly staff.
We had a room on the 6 floor with a city view. We could hear the guests in the next room watching tv and talking (clear enough to hear every word).. however this may be due to the old building/windows.
Reviewed on Jun 25, 2026
Stay near popular Bayside attractions
What to do in Bayside

Small Group Kayak Tour of Skyline in Milwaukee
$83
per adult

City of Neighborhoods: A Self-Guided Audio Tour in Milwaukee
$8
per adult
Bayside Hotel Deals

Potawatomi Hotel & Casino
1611 West Canal Street Milwaukee WI
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $201 total per night from Jul 5 to Jul 6
$201 total
Jul 5 - Jul 6
Total with taxes and fees
9.2/10 Wonderful! (1,570 reviews)
"Rooms very clean. Good security & sports book area is Awesome. People friendly and very nice cafe."
Reviewed on Jun 25, 2026

The Pfister Hotel
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $205 total per night from Jul 26 to Jul 27
$205 total
Jul 26 - Jul 27
Total with taxes and fees
9.6/10 Exceptional! (2,145 reviews)
"Hotel, staff and amenities were amazing. The only thing I could call out to be added was Pfister themed merchandise for sale"
Reviewed on Jun 25, 2026

Sheraton Milwaukee Brookfield Hotel
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $119 total per night from Jun 29 to Jun 30
$119 total
Jun 29 - Jun 30
Total with taxes and fees
8.4/10 Very Good! (916 reviews)
"The hotel was good. It was a little noisy in my room, but they put me on the top floor which apparently for club members and I’m not a club member so that was interesting. There’s no breakfast and the price was a little more than I wanted to pay but I couldn’t find anything better in the area."
Reviewed on Jun 24, 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.
Find the Best Bayside Vacation Packages
Bayside Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | General Mitchell Intl. Airport (MKE) |
Population | 4,400 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Harley-Davidson Museum, Milwaukee Art Museum and Riverside Theater |
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Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.




















