Upper East Side Holidays

Book a Hotel + Flight or Car together to unlock savings

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

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

Top hotels in Upper East Side

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 3.909.411 ₫ per night from 11 May to 12 May
3.909.411 ₫
4.609.197 ₫ total
11 May - 12 May
includes taxes & fees
9.2/10 Wonderful! (1,456 reviews)
Nice room, gym was very nice, food options in the various restaurants were wonderful. The hotel was clean and the room was comfortable. Self parking was easy and convenient. We will stay there again.

Reviewed on 6 May 2026

Potawatomi Hotel & Casino
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 4.185.834 ₫ per night from 31 May to 1 Jun
4.185.834 ₫
4.935.098 ₫ total
31 May - 1 Jun
includes taxes & fees
9.2/10 Wonderful! (1,101 reviews)
Nicely located and easy to get to

Reviewed on 6 May 2026

The Iron Horse 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 3.422.117 ₫ per night from 25 May to 26 May
3.422.117 ₫
4.034.676 ₫ total
25 May - 26 May
includes taxes & fees
9.6/10 Exceptional! (2,197 reviews)
Great stay! I knew we were getting a complimentary breakfast but I did not know we also got a complimentary dinner! Nice perks.

Reviewed on 7 May 2026

Drury Plaza Hotel Milwaukee Downtown
See all 1,145 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.

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 1null000null000 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.

Popular places to visit

American Family Field

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
Harley-Davidson Museum

Harley-Davidson Museum

You can spend an afternoon browsing the exhibits at Harley-Davidson Museum in Milwaukee. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Harley-Davidson Museum
Marquette University

Marquette University

Explore the campus of Marquette University during your visit to Milwaukee. Attend a sporting event or simply enjoy the lively breweries while you're in the area.

Marquette University