Whitefish Bay Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Whitefish Bay Vacation

Book a tailored Whitefish Bay vacation package that has only the things you need and nothing you don't. Great for families, nightlife and dining, think about staying in the neighborhood of East Town. If sightseeing is part of the program during your trip to Whitefish Bay, look around top attractions like Milwaukee Art Museum, Discovery World and Charles Allis Art Museum. Whatever your travel plans or budget, putting together the ultimate tailored Whitefish Bay vacation is a breeze with Expedia.

Top Holiday Package Deals in Whitefish Bay

Price found within the past 48 hours. Click for updated prices.
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,320, price is now CA $1,104 per person
CA $1,104
per person
Aug 29 - Aug 31
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.8/10 Exceptional! (2,655 reviews)
Beautiful room. The entry is dominated by a central bar. On night we stayed the bar was crowded and noisy. Did not bother room silenced but was jarring when entering hotspot and no way to get a seat or drink at bar. Great art but felt like NYC on Friday date nights.

Reviewed on Jun 14, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $1,611, price is now CA $1,164 per person
CA $1,164
per person
Aug 29 - Aug 31
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.6/10 Exceptional! (2,134 reviews)
Beautiful, historic hotel in downtown Milwaukee. Excellent location, allowing us to walk to various attractions. The staff was always friendly and helpful.

Reviewed on Jun 17, 2026

Dubbel Dutch

Dubbel Dutch

3 out of 5
Downtown Milwaukee
Price was CA $1,451, price is now CA $1,134 per person
CA $1,134
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.2/10 Wonderful! (148 reviews)
There is a bar in the building that is loud until midnight. The parking fee was higher than the site warranted. The sofa couch was not suitable for any over 5' tall. It all depends on the room you get in terms of the experience. I would not stay there again, as it was more costly and had little to recommend it. No microwave in the room. Fridge froze my food overnight, making it useless and uneatable. NOT appropriate if you cannot walk up steps easily. I think a regular hotel room would have offered better service at a more reasonable price.

Reviewed on Oct 28, 2025

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $1,800, price is now CA $1,449 per person
CA $1,449
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.2/10 Wonderful! (1,166 reviews)
Unique experience, neat place.

Reviewed on Jun 11, 2026

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was CA $1,606, price is now CA $1,352 per person
CA $1,352
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Milwaukee (MKE)
9.4/10 Exceptional! (471 reviews)
Great location! Steps away from all the charm and quirkiness that is Bayview. We had a beautiful room with a very comfy bed and a lovely bathroom. My husband and I enjoyed our stay here and had a delicious dinner at the restaurant downstairs (Sorella) on their patio. Would definitely recommend and come back again. (One small note- the walls are thin and you can hear people in the hallways and communal kitchen. So just make sure to pack some ear plugs)

Reviewed on Jun 16, 2026

Where to stay in Whitefish Bay

Find the best Whitefish Bay areas and neighborhoods for the activities you enjoy most. Learn more about Whitefish Bay
Downtown skyline with Buildings along the Milwaukee River, in Milwaukee, Wisconsin.; Shutterstock ID 523595590

Downtown Milwaukee

Central business district with cultural, financial, and historical landmarks, Downtown Milwaukee offers shopping at The Shops of Grand Avenue, art galleries in the Historic Third Ward, high-end dining, and vibrant nightlife. Explore the Milwaukee Public Market and Riverwalk, or hop on the free streetcar system.

Find hotels in Downtown Milwaukee

Whitefish Bay Hotel Deals

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
1611 West Canal Street Milwaukee WI
The price is CA $220 per night from Jun 29 to Jun 30
CA $220
CA $260 total
Jun 29 - Jun 30
includes taxes & fees
9.2/10 Wonderful! (1,555 reviews)
"The stay was okay. No one ever cleaned our room. We found out the day before we left that we had to request it. Also, I found out that I could have used the VIP parking but, I didn’t find out until the last day. The security was in overkill with my wife’s purse too. Always harassing her."

Reviewed on Jun 17, 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 $309 per night from Jun 29 to Jun 30
CA $309
CA $364 total
Jun 29 - Jun 30
includes taxes & fees
9.6/10 Exceptional! (2,130 reviews)
"Beautiful, historic hotel in downtown Milwaukee. Excellent location, allowing us to walk to various attractions. The staff was always friendly and helpful."

Reviewed on Jun 17, 2026

The Pfister Hotel
Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
375 S Moorland Rd Brookfield WI
The price is CA $148 per night from Jun 28 to Jun 29
CA $148
CA $171 total
Jun 28 - Jun 29
includes taxes & fees
8.4/10 Very Good! (894 reviews)
"Upgrading to the Club Lounge was the best decision! This hotel has a great location with lots nearby. Regretting not staying longer. The building is clearly older but they've done a nice job updating the decor."

Reviewed on Jun 16, 2026

Sheraton Milwaukee Brookfield Hotel
See all 1,161 properties in Whitefish Bay
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

Frequently asked questions

How much does a Whitefish Bay vacation package cost?
You can snap up a vacation package to this destination from CA $1,104 on Expedia. However, how much your vacation to Whitefish Bay costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Whitefish Bay?
January, February and November are great times to search for cheap Whitefish Bay vacation packages. Choosing to travel in quieter periods means you'll typically find lower prices on flights and hotels.
How many days is enough for Whitefish Bay?
We'd suggest booking a Whitefish Bay vacation for around 2 days. This will allow you enough time to visit top attractions including Milwaukee River Walk and Riverside Theatre, and also explore neighbourhoods like Downtown Milwaukee and East Town. You could even make time for one or two day trips from Whitefish Bay.
How to find the best Whitefish Bay package deals?
Start your search for a Whitefish Bay package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Whitefish Bay package deal right away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Whitefish Bay getaway off to a flying start.
Is it cheaper to book a Whitefish Bay vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking stays and flights separately. Better still, you can tailor your Whitefish Bay escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Whitefish Bay?
Score amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Whitefish Bay escape.
How to plan a trip to Whitefish Bay?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Whitefish Bay.
  2. Plan your budget wisely: In addition to the price of your accommodations, you should consider other expenses. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that may arise during your trip to Whitefish Bay.
  3. Decide how long to go away for: Now that you know more about Whitefish Bay, you can figure out the right length of your break. Pull together a draft itinerary and allocate enough time to cover everything you want to see.
  4. Combine your airfare and accommodations: After you've nailed down your dates and duration, lock in the perfect Whitefish Bay vacation package for you.

Stay near popular Whitefish Bay attractions

Klode Park

After visiting Klode Park, make a plan to see the other sights and activities in Milwaukee. Attend a sporting event or simply enjoy the lively breweries while you're in the area.
See properties

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.