Bayside Vacation Packages

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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.

Top Bayside Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $1,786, price is now CA $1,407 per person
CA $1,407
per person
Aug 28 - Aug 31
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.2/10 Wonderful! (1,192 reviews)
.

Reviewed on Jul 15, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $2,231, price is now CA $1,491 per person
CA $1,491
per person
Aug 28 - Aug 31
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.6/10 Exceptional! (2,139 reviews)
We were in Milwaukee for our son’s engagement. I had scheduled some special deserts to be shipped from NewJersey. I had called the hotel and advised them to refrigerate the box immediately when received. I was assured that they would take care of it. However when we arrived, and were ready to leave for the engagement we were informed that they had put the box in the freezer instead of the refrigerator. Also the management did not make any attempt to apologize for messing this up for us. Extremely bad customer service.

Reviewed on Jul 14, 2026

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,839, price is now CA $1,567 per person
CA $1,567
per person
Aug 28 - Aug 31
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.8/10 Exceptional! (2,652 reviews)
Wonderful stay at a great location! Walking distance to a lot of places and restaurants. Amazing and friendly staff. Will definitely stay here again.

Reviewed on Jul 13, 2026

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Menomonee River Valley
Price was CA $1,602, price is now CA $1,438 per person
CA $1,438
per person
Aug 28 - Aug 31
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.2/10 Wonderful! (1,592 reviews)
I really enjoyed my stay here. The room had a casino, and that was part of the reason for my stay.

Reviewed on Jul 15, 2026

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

4 out of 5
Marquette
Price was CA $1,586, price is now CA $1,440 per person
CA $1,440
per person
Aug 28 - Aug 31
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9/10 Wonderful! (1,342 reviews)
Great spot!!

Reviewed on Jul 14, 2026

Ready to book your vacation to Bayside?

 

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Bayside Hotel Deals

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
1611 West Canal Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $221 per night from Jul 28 to Jul 29
CA $221
CA $261 total
Jul 28 - Jul 29
includes taxes & fees
9.2/10 Wonderful! (1,666 reviews)
"I really enjoyed my stay here. The room had a casino, and that was part of the reason for my stay."

Reviewed on Jul 15, 2026

Potawatomi Hotel & Casino
The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $280 per night from Jul 29 to Jul 30
CA $280
CA $330 total
Jul 29 - Jul 30
includes taxes & fees
9.6/10 Exceptional! (2,154 reviews)
"We were in Milwaukee for our son’s engagement. I had scheduled some special deserts to be shipped from NewJersey. I had called the hotel and advised them to refrigerate the box immediately when received. I was assured that they would take care of it. However when we arrived, and were ready to leave ..."

Reviewed on Jul 14, 2026

The Pfister Hotel
Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Jul 19 to Jul 20
CA $149
CA $172 total
Jul 19 - Jul 20
includes taxes & fees
8.4/10 Very good! (974 reviews)
"Outdoor pool was not opened and was drained. Very disappointing since that’s one of the reasons why we chose Sheraton."

Reviewed on Jul 14, 2026

Sheraton Milwaukee Brookfield Hotel
See all 1,183 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
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Stay near popular Bayside attractions

Lynden Sculpture Garden

Explore the great outdoors at Lynden Sculpture Garden, a lovely green space in River Hills. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
See properties

What to do in Bayside

Milwaukee Food Tour with 5 Local Favorites Tastings & Secret Dish

Milwaukee Food Tour with 5 Local Favorites Tastings & Secret Dish

CA $145
per adult
Milwaukee Food Tour with 5 Local Favorites Tastings & Secret Dish
City of Neighborhoods: A Self-Guided Audio Tour in Milwaukee

City of Neighborhoods: A Self-Guided Audio Tour in Milwaukee

CA $11
per adult
City of Neighborhoods: A Self-Guided Audio Tour in Milwaukee
Small Group Kayak Tour of Skyline in Milwaukee

Small Group Kayak Tour of Skyline in Milwaukee

CA $118
per adult
Small Group Kayak Tour of Skyline in Milwaukee
See all activities in Bayside

Frequently asked questions

How much does a Bayside vacation package cost?
Offering great value package deals from CA $1,407 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.

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.