Upper East Side Vacation Packages

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Where to stay in Upper East Side

Find the best Upper East Side areas and neighborhoods for the activities you enjoy most. Learn more about Upper East Side
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

Upper East Side 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 $204 per night from May 20 to May 21
CA $204
CA $241 total
May 20 - May 21
includes taxes & fees
9.2/10 Wonderful! (1,486 reviews)
"The location is prime near many Of Milwaukee's sights. It's located in the heart of downtown Milwaukee and not far from many things. The staff from check in to check out, were exceptional, the property well maintained and cleaned. I requested a room overlooking the downtown area and lake michigan.East ..."

Reviewed on May 16, 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 $234 per night from Jun 14 to Jun 15
CA $234
CA $276 total
Jun 14 - Jun 15
includes taxes & fees
9.6/10 Exceptional! (2,113 reviews)
"Another great stay at the best-updated of all the Grand Dame hotels I've ever seen. Every staffer was nice and the onsite cafe and bars were terrific. Comfortable room, good wifi and sensible TV features - everything just great."

Reviewed on May 17, 2026

The Pfister 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
The price is CA $234 per night from May 31 to Jun 1
CA $234
CA $276 total
May 31 - Jun 1
includes taxes & fees
9.2/10 Wonderful! (1,126 reviews)
"Unique hotel. The rooms are cool. There was no soap to wash your hands though. You had to get body wash from the shower. That was annoying. I’d still stay there again though."

Reviewed on May 16, 2026

The Iron Horse Hotel
See all 1,137 properties in Upper East Side
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.
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Frequently asked questions

How much does an Upper East Side vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Upper East Side from just . And the more you bundle, the more dollars you save. Your dream vacation has never been so affordable.
How do I get a cheap travel package to Upper East Side?
Booking a hotel and flight together with Expedia won't just save valuable time — it'll save you money too. An Upper East Side vacation package makes it a breeze to create your dream adventure. With more than 550 airlines around the world to choose from, finding flights that suit your busy schedule won't be hard. In addition to that, we have over 1,000,000 hotel options globally to choose from. Now that's choice! No matter who you are, Expedia can show you the world.
Where should I stay in Upper East Side?
Make sightseeing easier by staying in a hotel just a stone's throw away from Upper East Side's main attractions. Milwaukee Art Museum and American Family Field are two of the best in the area.
What are the top hotels in Upper East Side?
If it's your very first time in Upper East Side, make a reservation at Flexhome East Side Studio Es2 - Uwm+rooftop+lounge or A Must See 1897 Historic Victorian In A Fantastic Safe Area. Both hotels will make you feel at home and are favorites with lots of travelers.
How far in advance should I book my Upper East Side vacation?
Savvy travelers book early. Airlines typically release flight tickets up to a year ahead of departure, and this is a perfect opportunity to pick up some of the lowest prices. Just been told you should take all your vacation days next month? That's fine too — Expedia are never short of fantastic bargains to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia Upper East Side travel package include?
That depends on what type of escape you have in mind. Upper East Side vacation deals can include car rentals, hotels and flights. You can mix and match to create the package that suits you. You can also add on experiences and activities after you've booked to score even bigger discounts.
What should I know before booking an Upper East Side travel package?
When you book your hotels, flights and car rentals together, you'll pick up fantastic discounts. Whether you're organizing a mountain getaway in a cabin or would rather stay in a luxurious city hotel, Expedia will help make it happen.
Can I choose my airline with an Upper East Side Expedia vacation package?
You can, and with over 550 airlines to pick from across the globe, you've got lots of choice. Have a look through the available options and find out which airline best fits your needs and budget.
If I'm not able to travel, can I cancel my Upper East Side vacation package?
Don't worry if you're rethinking your Upper East Side vacation package — it's possible to cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We know your circumstances can change suddenly, so look up our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.

Discover the most popular places to visit in Upper East Side

Harley-Davidson Museum

Harley-Davidson Museum

5/5(13 reviews)

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 Art Museum

Milwaukee Art Museum

5/5(12 reviews)

Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.

Milwaukee Art Museum

Potawatomi Bingo Casino

Why not roll the dice with a visit to Potawatomi Bingo Casino during your time in Milwaukee? Attend a sporting event or simply enjoy the lively breweries while you're in the area.

Potawatomi Bingo Casino

Things to do

Small Group Kayak Tour of Skyline in Milwaukee

Small Group Kayak Tour of Skyline in Milwaukee

CA $114
per adult
Small Group Kayak Tour of Skyline in Milwaukee
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.