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 Milwaukee City Hall 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

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 4.392.656 ₫ per night from 24 Feb to 25 Feb
4.392.656 ₫
5.178.738 ₫ total
24 Feb - 25 Feb
includes taxes & fees
9.6/10 Exceptional! (1,989 reviews)
The staff are so incredibly attentive, the hotel is stunning, the prices are good. We will stay here agin!

Reviewed on 21 Feb 2026

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 4.320.306 ₫ per night from 11 Mar to 12 Mar
4.320.306 ₫
5.093.640 ₫ total
11 Mar - 12 Mar
includes taxes & fees
9.8/10 Exceptional! (2,564 reviews)
Saint Kates has a desirable location, good vibed lounge and bar area, polite staff and unique food drink options.

Reviewed on 21 Feb 2026

Saint Kate - The Arts Hotel
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 2.409.715 ₫ per night from 8 Mar to 9 Mar
2.409.715 ₫
2.841.053 ₫ total
8 Mar - 9 Mar
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
The room was clean. Check in was easy. Felt safe and quiet from outside noise. The walls are thin. The bed is hard and squeaks when you move. The pillows have no support and the sheets were scratchy. From what i could tell, no way to change the temperature in the room.

Reviewed on 21 Feb 2026

The Knickerbocker on the Lake
See all 1,108 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

Outfield sign at miller park

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 showing interior views

Harley-Davidson Museum

4.5/5(3 reviews)

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

Harley-Davidson Museum
Downtown, Milwaukee

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