Bayside Vacations from $340

Book a Hotel + Flight or Car together to unlock savings

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.
Super 8 by Wyndham Sturtevant/Racine

Super 8 by Wyndham Sturtevant/Racine

2 out of 5
Price was $410, price is now $340 per person
$340
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Milwaukee (MKE)
7.6/10 Good! (654 reviews)
There was a couple stains on towels and the staff was great.

Reviewed on Dec 31, 2025

The Stella Hotel & Ballroom

The Stella Hotel & Ballroom

3.5 out of 5
Downtown Kenosha
Price was $527, price is now $427 per person
$427
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Milwaukee (MKE)
9.4/10 Exceptional! (1,001 reviews)
Bed sucked ass and no alarm clock.

Reviewed on Dec 31, 2025

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was $1,008, price is now $826 per person
$826
per person
Mar 19 - Mar 22
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
9.2/10 Wonderful! (1,008 reviews)
Friendly staff. Shay was so helpful. Max, the bartender, was super cool and makes awesome drinks. Clean room. Comfy bed and pillows. Spacious fridge. Nice views of downtown. Valet staff was efficient. Recommend 100%!!! .

Reviewed on Jan 13, 2026

Lake Lawn Resort

Lake Lawn Resort

3.5 out of 5
Price was $465, price is now $385 per person
$385
per person
Mar 26 - Mar 29
found 10 hours ago
Roundtrip flight included
Philadelphia (PHL) to Milwaukee (MKE)
9/10 Wonderful! (1,002 reviews)
Beautiful rooms, friendly staff. Only small complaint is that the hot tub still has sand on the bottom from summer- our visit was in January. Other than that, it was great!

Reviewed on Jan 8, 2026

Comfort Inn & Suites Kenosha-Pleasant Prairie

Comfort Inn & Suites Kenosha-Pleasant Prairie

3 out of 5
Price was $488, price is now $407 per person
$407
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Milwaukee (MKE)
8.4/10 Very Good! (1,005 reviews)
The room was great - loved the separate office space where one of could read without the light disturbing the other person sleeping. Also, the location is very convenient.

Reviewed on Jan 12, 2026

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Discover the most popular places to visit in Bayside

Outfield sign at miller park

American Family Field

Catch an event at American Family Field during your trip to Milwaukee. Attend a baseball game or simply enjoy the lively breweries while you're in the area.

American Family Field
Harley-Davidson Museum showing 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 County Zoo featuring interior views and zoo animals as well as a small group of people

Milwaukee County Zoo

This sprawling animal park houses a wide array of exotic wildlife, and is acclaimed for its conservation programs and educational resources.

Milwaukee County Zoo

What to do in Bayside

The Grand Walk: A Self-Guided Audio Tour through Milwaukee

The Grand Walk: A Self-Guided Audio Tour through Milwaukee

$9
per adult
80% of travellers recommend
The Grand Walk: A Self-Guided Audio Tour through Milwaukee
At the Pabst, Captain Frederick Pabst can been seen smoking backstage on a ghost tour of Milwaukee with Brew City Ghosts

Milwaukee Morbid Mirrorlight Ghost Tours

$32
per adult
Milwaukee Morbid Mirrorlight Ghost Tours
Milwaukee : Best Street Food Private Tour With A Local Guide

Milwaukee Best Street Food Tour With A Local Guide

$109
per adult
Milwaukee Best Street Food Tour With A Local Guide
See all activities in Bayside

Bayside Hotel Deals

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$150 nightly
The price is $177 total per night from Feb 5 to Feb 6
$177 total
Feb 5 - Feb 6
Total with taxes and fees
9.4/10 Exceptional! (1,876 reviews)
Mia at front desk was super sweet and helpful. Room was great as well.

Reviewed on Jan 12, 2026

The Pfister Hotel
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $128 total per night from Jan 28 to Jan 29
$128 total
Jan 28 - Jan 29
Total with taxes and fees
9.6/10 Exceptional! (2,515 reviews)
Great hotel! So fun and unique. Very clean and personalized

Reviewed on Jan 11, 2026

Saint Kate - The Arts Hotel
The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
500 W Florida Street Milwaukee WI
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $169 total per night from Jan 28 to Jan 29
$169 total
Jan 28 - Jan 29
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
Friendly staff. Shay was so helpful. Max, the bartender, was super cool and makes awesome drinks. Clean room. Comfy bed and pillows. Spacious fridge. Nice views of downtown. Valet staff was efficient. Recommend 100%!!! .

Reviewed on Jan 13, 2026

The Iron Horse Hotel
See all 1,116 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.

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

How much does a Bayside vacation package cost?
You'll find cheap prices from $340 on Expedia for your Bayside escape. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Bayside costs.
What are the cheapest months to go to Bayside?
If you're looking to book a cheap Bayside vacation package, consider visiting in January, October and December. You'll generally find better rates on airfares and hotels during these months — ideal for travelers wishing to save money.
How many days is enough for Bayside?
The ideal length for your Bayside vacation depends on what you'd like to do. Typically, a handful of days to a week will give you enough time to hit all the main attractions and discover some hidden spots along the way.
Is it worth booking a vacation package to Bayside?
It's easy to see why a Bayside vacation is on the to-do list of many travelers. Well-known attractions like Schlitz Audubon Nature Center are just the beginning of things to keep you busy here.
How to find the best Bayside package deals?
Bagging a cheap Bayside package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Bayside package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Bayside vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component separately. And you'll still enjoy the freedom to create a customized Bayside vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Bayside?
If you're considering a spontaneous Bayside adventure, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land incredible deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Bayside vacation packages?
Your Bayside trip is meant to be an escape from your busy life, not a reason for money worries. So to allow you extra flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.