Upper East Side Holidays

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Your Upper East Side Holiday

Make travel planning stress-free by reserving a holiday package to Upper East Side. Let us handle the finer points, so you can focus on discovering everything this neighbourhood can offer. Hoping to see the sights during your trip to Upper East Side? Pencil in a visit to nearby attractions like Milwaukee Art Museum, Discovery World and Charles Allis Art Museum. Stop daydreaming and start doing. When you're ready to book your ideal holiday to Upper East Side, Expedia will help you get there.

Our guide on 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
Milwaukee

Downtown Milwaukee

Lake Michigan and Pabst Theater are a few top attractions in Downtown Milwaukee. Hop around the city on the metro at Michigan & Jackson Tram Stop or Clybourn & Jefferson Tram Stop and check out the area's fantastic nightlife, stunning river views and acclaimed art galleries.

Find hotels in Downtown Milwaukee

Our pick of the best Upper East Side 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
The price is AU$270 per night from 26 Dec to 27 Dec
AU$270
26 Dec - 27 Dec
includes taxes & fees
9.4/10 Exceptional! (1,794 reviews)
Brian got us to our room and set the tone for this fabulous, gorgeous hotel stay. Everyone was very helpful and made our stay special.

Reviewed on 7 Dec 2025

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
The price is AU$236 per night from 21 Dec to 22 Dec
AU$236
21 Dec - 22 Dec
includes taxes & fees
9.6/10 Exceptional! (2,447 reviews)
Yup!

Reviewed on 2 Dec 2025

Saint Kate - The Arts Hotel
Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

3 out of 5
700 N. Water Street Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is AU$178 per night from 1 Jan to 2 Jan
AU$178
1 Jan - 2 Jan 2026
includes taxes & fees
9.6/10 Exceptional! (2,001 reviews)
The room was spotless. The shower was wonderful. We got hot water right away and plenty of towels. Amenities were readily available. The hot breakfast and the kickback at 5:30pm were also a wonderful addition to the stay. The food was delicious and the service was also great. Everything was also ...

Reviewed on 5 Dec 2025

Drury Plaza Hotel Milwaukee Downtown
See all 1,142 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
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Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does an Upper East Side holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Upper East Side from just . And the more you bundle, the more dollars you save. Your dream holiday 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 holiday 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 favourites with lots of travellers.
How far in advance should I book my Upper East Side holiday?
Savvy travellers 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 holiday 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 holiday 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 organising 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 holiday 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 holiday package?
Don't worry if you're rethinking your Upper East Side holiday 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 which includes 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 zoo animals and interior views 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

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

Activities

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

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

AU$14
per adult
80% of travellers recommend
The Grand Walk: A Self-Guided Audio Tour through Milwaukee
Grohmann Museum at Milwaukee School of Engineering

Skip the Line: Museum Admission Ticket - Grohmann Museum

AU$8
per adult
Skip the Line: Museum Admission Ticket - Grohmann Museum
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

AU$49
per adult
Milwaukee Morbid Mirrorlight Ghost Tours
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.