Yankee Hill Vacation Packages

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

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Top Holiday Package Deals in Yankee Hill

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Milwaukee Brookfield

Embassy Suites by Hilton Milwaukee Brookfield

3.5 out of 5
Price was CA $998, price is now CA $889 per person
CA $889
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9/10 Wonderful! (1,320 reviews)
Love this hotel. Very clean and great staff and great amenities. Stay here whenever I come to Brookfield.

Reviewed on Jul 28, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was CA $1,644, price is now CA $1,092 per person
CA $1,092
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Milwaukee (MKE)
9.6/10 Exceptional! (2,164 reviews)

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was CA $1,294, price is now CA $1,066 per person
CA $1,066
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.2/10 Wonderful! (1,226 reviews)

Kinn Guesthouse Downtown

Kinn Guesthouse Downtown

4.5 out of 5
Downtown Milwaukee
Price was CA $1,612, price is now CA $1,397 per person
CA $1,397
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.4/10 Exceptional! (387 reviews)
Great place, first impression I wasn’t sure if I was in the right place since it was booked for me. Beautiful building, built in the 1800s. Rooms are amazing. Since it is in downtown Milwaukee, it does get a little loud but it’s to be expected. We’ll definitely stay here again.

Reviewed on Jul 30, 2026

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Menomonee River Valley
Price was CA $1,588, price is now CA $1,402 per person
CA $1,402
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.2/10 Wonderful! (1,682 reviews)
Overall good experience. Seamless check in & check out.

Reviewed on Jul 31, 2026

Where to stay in Yankee Hill

Find the best Yankee Hill areas and neighborhoods for the activities you enjoy most. Learn more about Yankee Hill
A river with a city skyline, including a tall building with a pointed roof, and a park with yellow trees.

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

Yankee Hill Hotel Deals

The Knickerbocker on the Lake

The Knickerbocker on the Lake

3 out of 5
1028 East Juneau Avenue Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Aug 30 to Aug 31
CA $154
CA $181 total
Aug 30 - Aug 31
includes taxes & fees
8.8/10 Excellent! (1,025 reviews)
"The room was clean and very comfortable, but the online check in was unnecessarily detailed, lengthy and complicated. That experience might discourage me from staying there again."

Reviewed on Jul 30, 2026

The Knickerbocker on the Lake
The Plaza Hotel

The Plaza Hotel

3 out of 5
1007 N Cass Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from Aug 17 to Aug 18
CA $225
CA $265 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (1,216 reviews)
"This is a beautifully updated historic building that holds on to and respects the deco details and charm. Hotel rooms sfeel modern and are clean ( seems updated since the last time we stayed here a couple of years ago) and the location can't be beat on the East Side of Milwaukee. The cafe/ restaurant ..."

Reviewed on Jul 30, 2026

The Plaza Hotel
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 $340 per night from Aug 9 to Aug 10
CA $340
CA $401 total
Aug 9 - Aug 10
includes taxes & fees
The Pfister Hotel
See all 1,156 properties in Yankee Hill
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
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Frequently asked questions

How much does a Yankee Hill vacation package cost?
Starting from only CA $889, a package is your gateway to inexpensive travel. Put together your Yankee Hill escape by picking from our huge range of hotels, airfares and rental cars.
How do I get a cheap travel package to Yankee Hill?
Bundle your hotels and flights with Expedia to save big bucks on your next trip. With over 550 airlines and 1,000,000 properties around the globe, your Yankee Hill vacation package can be customized exactly to suit your budget. With all that extra money, why not include one or more awesome experiences and tours? It's an easy way to unlock even more discounts. Your dream vacation in Yankee Hill is closer than you thought!
Where should I stay in Yankee Hill?
Vacationers come from all over the world to experience Milwaukee Art Museum and American Family Field in Yankee Hill. Stay within a stone's throw of these popular attractions to make sightseeing easy.
What are the top hotels in Yankee Hill?
Book a stay at County Clare Irish Hotel & Pub. It's one of this neighborhood's most in-demand hotels. Another highly rated option in Yankee Hill is Park East Hotel.
How far in advance should I book my Yankee Hill vacation?
Reserving your seat early with Expedia means one less thing to worry about. Most air carriers advertise prices up to 12 months in advance. This is typically the cheapest time to book. If circumstances have left you booking late, incredible deals to Yankee Hill sometimes emerge just weeks before departure.
What does an Expedia Yankee Hill travel package include?
Much of that depends on you. You can choose from a range of Yankee Hill bundles, such as a hotel, flight and rental car. You can also book a flight with a hotel, or a rental car with a flight. Once you've made your booking, you can add on the fun stuff like experiences and activities. Whatever your Yankee Hill escape looks like, get set to save!
What should I know before booking a Yankee Hill travel package?
You can save a tidy sum by combining your hotels, flights and rental cars. Once you've made your booking, you can add on things like day tours or experiences. Your next awesome vacation is only a couple of clicks away.
Can I choose my airline with a Yankee Hill Expedia vacation package?
Yes, you're in charge. We have access to over 550 partner airlines around the world, so you can tailor your Yankee Hill trip according to your travel preferences.
If I'm not able to travel, can I cancel my Yankee Hill vacation package?
You can. We realize life doesn't always go to plan, so we're happy to help if you need to make changes to your Yankee Hill vacation package. You may be able to amend or cancel your itinerary at no cost if you've booked in the last 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Take a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the nitty-gritty on change fees.

Things to do

View of E. Wisconsin Ave. looking towards Lake Michigan

Downtown Milwaukee Walking Tour

CA $23
per adult
Downtown Milwaukee Walking Tour
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
Haunting Histories: An Audio Tour of Milwaukee‘s Wicked Westown

Haunting Histories: An Audio Tour of Milwaukee‘s Wicked Westown

CA $13
per adult
Haunting Histories: An Audio Tour of Milwaukee‘s Wicked Westown
See all activities in Milwaukee
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.