Bayside Vacations from $579

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.
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

4 out of 5
Marquette
Price was $687, price is now $579 per person
$579
per person
Dec 28 - Jan 1
found 8 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Milwaukee (MKE)
9/10 Wonderful! (1,417 reviews)
beds were comfortable and the hotel decor was awesome, inside & outside the building. I was not aware there was no free parking, the cost is $30 as well as a $50 deposit. They also try to get you to join Wyndam rewards or pay for WiFi until you complain to the front desk and they give you an access code to use for free WiFi. Hotel staff is not helpful if you are looking for local things to do or a local map of areas of interest. Michael's restaurant on the next block has very good food at a reasonable price. The decorative elevator doors ae not automatic so it is challenging to get the luggage cart through the door while holding it open. It is nice they have a free shuttle service within 3 miles.

Reviewed on Oct 27, 2026

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was $816, price is now $617 per person
$617
per person
Dec 28 - Jan 1
found 8 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Milwaukee (MKE)
9.2/10 Wonderful! (1,378 reviews)

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was $889, price is now $674 per person
$674
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
San Jose (SJC) to Milwaukee (MKE)
9.6/10 Exceptional! (2,299 reviews)
Clean rooms, top floor pool, easy in/out parking, great gym, helpful staff & beautiful architecture.

Reviewed on Oct 26, 2026

Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Downtown Milwaukee
Price was $1,364, price is now $1,054 per person
$1,054
per person
Dec 28 - Jan 1
found 8 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Milwaukee (MKE)
9.4/10 Exceptional! (444 reviews)
great staff

Reviewed on Oct 27, 2026

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was $796, price is now $650 per person
$650
per person
Dec 28 - Jan 1
found 8 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Milwaukee (MKE)
9.4/10 Exceptional! (508 reviews)

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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

Grohmann Museum

Skip the Line: Museum Admission Ticket - Grohmann Museum

$5
per adult
Skip the Line: Museum Admission Ticket - Grohmann Museum
Milwaukee Morbid Mirrorlight Ghost Tours

Milwaukee Morbid Mirrorlight Ghost Tours

$26
per adult
Milwaukee Morbid Mirrorlight Ghost Tours
View of E. Wisconsin Ave. looking towards Lake Michigan

Downtown Milwaukee Walking Tour

$16
per adult
Downtown Milwaukee Walking Tour
See all activities in Bayside

Bayside Hotel Deals

Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

4 out of 5
333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is $99 total per night from Nov 9 to Nov 10
$99 total
per night
Nov 9 - Nov 10
Hyatt Regency Milwaukee
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 $100 total per night from Nov 8 to Nov 9
$100 total
per night
Nov 8 - Nov 9
Sheraton Milwaukee Brookfield Hotel
Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

4 out of 5
700 N. Water Street Milwaukee WI
The price is $137 total per night from Nov 15 to Nov 16
$137 total
per night
Nov 15 - Nov 16
9.6/10 Exceptional! (2,429 reviews)
"Was a fantastic place in a great location. Would stay again without question!"

Reviewed on Oct 27, 2026

Drury Plaza Hotel Milwaukee Downtown
See all 1,150 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 $579 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.