Bayside Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Elizabeth Baumann

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, 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.
DoubleTree by Hilton Milwaukee - Brookfield

DoubleTree by Hilton Milwaukee - Brookfield

4 out of 5
Price was CA $851, price is now CA $682 per person
CA $682
per person
Oct 3 - Oct 6
found 23 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
8.4/10 Very Good! (1,002 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 Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Downtown Milwaukee
Price was CA $1,266, price is now CA $1,022 per person
CA $1,022
per person
Oct 3 - Oct 6
found 23 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.4/10 Exceptional! (287 reviews)
The property was easy to check in to. Only bad thing was our shower water had only two option hot and scalding hot. I like that they offered discounted overnight parking from a parking garage nearby. All of the other guest were respectful.

Reviewed on Aug. 24, 2025

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,131, price is now CA $925 per person
CA $925
per person
Oct 3 - Oct 6
found 23 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.8/10 Exceptional! (2,385 reviews)
The hotel itself is unique and still the perfect room for comfort and cleanliness. Easy checkin with a glass of champagne. Loved the lobby bar with great bartenders. Great overall hotel close to many arts opportunities, but especially convenient when attending a show at Pabst Theater. Great experience!

Reviewed on Aug. 26, 2025

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Price was CA $1,089, price is now CA $909 per person
CA $909
per person
Oct 3 - Oct 6
found 23 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9/10 Wonderful! (1,340 reviews)
The rooms are very nice and clean. I liked that they had adjoining rooms for two families. Easy uber picked to go to Summerfest grounds.

Reviewed on Aug. 25, 2025

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was CA $1,105, price is now CA $924 per person
CA $924
per person
Oct 3 - Oct 6
found 22 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Milwaukee (MKE)
9.6/10 Exceptional! (406 reviews)
Beautiful room & great common area... I wish we had a bit more time to spend there!

Reviewed on Aug. 27, 2025

Ready to book your vacation to Bayside?

 

Choose your dates

Bayside Hotel Deals

Sonesta Milwaukee West Wauwatosa

Sonesta Milwaukee West Wauwatosa

3.5 out of 5
10499 W Innovation Dr, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is CA $116 per night from Sep 2 to Sep 3
CA $116
CA $134 total
Sep 2 - Sep 3
includes taxes & fees
7.4/10 Good! (1,594 reviews)
"Clean, convenient and kind staff."

Reviewed on Aug. 23, 2025

Sonesta Milwaukee West Wauwatosa
AmericInn by Wyndham Glendale/Milwaukee

AmericInn by Wyndham Glendale/Milwaukee

2.5 out of 5
5110 N Port Washington Rd, (772), Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is CA $97 per night from Sep 9 to Sep 10
CA $97
CA $113 total
Sep 9 - Sep 10
includes taxes & fees
7.6/10 Good! (1,011 reviews)
"Good breakfast. Convenient to where we were visiting."

Reviewed on Aug. 24, 2025

AmericInn by Wyndham Glendale/Milwaukee
Sonesta Select Milwaukee Brookfield

Sonesta Select Milwaukee Brookfield

3 out of 5
16865 W Bluemound Rd, Brookfield, WI
Fully refundableReserve now, pay when you stay
The price is CA $116 per night from Sep 15 to Sep 16
CA $116
CA $134 total
Sep 15 - Sep 16
includes taxes & fees
8/10 Very Good! (1,267 reviews)
"Nice and clean"

Reviewed on Aug. 25, 2025

Sonesta Select Milwaukee Brookfield
See all 1,223 properties in Bayside
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Bayside

Harley-Davidson Museum featuring interior views

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.

Harley-Davidson Museum
Milwaukee Art Museum

Milwaukee Art Museum

Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.

Milwaukee Art Museum

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.

Potawatomi Bingo Casino

What to do in Bayside

Grohmann Museum at Milwaukee School of Engineering

Skip the Line: Museum Admission Ticket - Grohmann Museum

CA $7
per adult
Skip the Line: Museum Admission Ticket - Grohmann Museum
A Romantic Journey Through Milwaukee

A Romantic Journey Through Milwaukee

CA $1,077
per adult
A Romantic Journey Through Milwaukee
At the Pabst, Captain Frederick Pabst can been seen smoking backstage on a ghost tour of Milwaukee with Brew City Ghosts

Brew City Ghosts: Macabre Milwaukee By US Ghost Adventures

CA $36
per adult
Brew City Ghosts: Macabre Milwaukee By US Ghost Adventures
See all activities in Bayside

Frequently asked questions

How much does a Bayside vacation package cost?
Offering great value package deals from CA $682 on Expedia, you'll be thrilled with how little a vacation to Bayside costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Bayside?
You're likely to find reduced prices and better availability in January, February and November. Take a look at our cheap Bayside vacation packages and you could score some excellent off-season deals.
How many days is enough for Bayside?
For a Bayside vacation, a handful of days will be enough to tour all the highlights. Make sure to stop by Schlitz Audubon Nature Centre — it's one of the leading attractions in this destination. If you're looking for more activities, consider basing yourself here and heading off on some day tours from Bayside.
How to find the best Bayside package deals?
Use Expedia's filters to help you find some unbeatable Bayside package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Bayside package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Bayside vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging hotels and flights individually. Better still, you can personalize your Bayside escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Bayside?
Enjoy incredible bargains by booking your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Bayside getaway.
How to plan a trip to Bayside?

  1. Choose your travel dates: What you plan to do in Bayside and your favourite season can help you decide when to travel.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and meals to flights and activities. Your hotel will probably be the biggest expense during your trip to Bayside.
  3. Decide how many days away: Start by listing all the attractions you'd like to experience in Bayside. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your accommodations and airfare: After you've settled on your dates and duration, lock in the perfect Bayside vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.