Upper East Side Vacations from $348

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Your Upper East Side Vacation

Make travel planning stress-free by reserving a vacation package to Upper East Side. Let us handle the finer points, so you can focus on discovering everything this neighborhood 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 vacation to Upper East Side, Expedia will help you get there.

The Latest Upper East Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Wildwood Lodge

Wildwood Lodge

2.5 out of 5
Price was $436, price is now $348 per person
$348
per person
Jan 15 - Jan 18
found 11 hours ago
Roundtrip flight included
New York (NYC) to Milwaukee (MKE)
8.4/10 Very Good! (1,001 reviews)
Customer Service & Hospitality was as if I was a prodigal son returning Home after almost 25 years of active service in the Military. Very warming & peaceful. Will return for a full retreat, soon!

Reviewed on Dec 2, 2025

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was $746, price is now $533 per person
$533
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Milwaukee (MKE)
9.6/10 Exceptional! (428 reviews)
The room was great, location was perfect. I loved the loft vibe and exposed brick. It would have been a 5 star review if the TV was working. We couldn't get the TV to turn on.

Reviewed on Nov 5, 2025

Hilton Milwaukee

Hilton Milwaukee

4 out of 5
Westown
Price was $930, price is now $714 per person
$714
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Milwaukee (MKE)
8.4/10 Very Good! (1,075 reviews)
Last minute booking and in a new part of town I usually stay. Very good hotel

Reviewed on Nov 29, 2025

Courtyard by Marriott Milwaukee Downtown

Courtyard by Marriott Milwaukee Downtown

3 out of 5
Westown
Price was $737, price is now $579 per person
$579
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Milwaukee (MKE)
8.6/10 Excellent! (1,004 reviews)
Friendly staff, clean room

Reviewed on Nov 9, 2025

Holiday Inn Express Milwaukee-West Medical Center by IHG

Holiday Inn Express Milwaukee-West Medical Center by IHG

2.5 out of 5
Wauwatosa
Price was $530, price is now $423 per person
$423
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Milwaukee (MKE)
7.8/10 Good! (1,001 reviews)
Room spotless, staff helpful, breakfasts a plus.

Reviewed on Dec 1, 2025

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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
Milwaukee

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

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $140 total per night from Dec 21 to Dec 22
$140 total
Dec 21 - Dec 22
Total with taxes and fees
9.4/10 Exceptional! (1,812 reviews)
Ive stayed here many times, never disappointed.

Reviewed on Dec 1, 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
$104 nightly
The price is $122 total per night from Dec 28 to Dec 29
$122 total
Dec 28 - Dec 29
Total with taxes and fees
9.6/10 Exceptional! (2,447 reviews)
Wonderful staff, courteous and kind!

Reviewed on Nov 27, 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
$100 nightly
The price is $118 total per night from Jan 1 to Jan 2
$118 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
9.6/10 Exceptional! (2,018 reviews)
They did not have the room available that I reserved. The front desk staff did their best to try to make it right. The room was fine.

Reviewed on Nov 28, 2025

Drury Plaza Hotel Milwaukee Downtown
See all 1,148 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Kid Friendly Vacations

Discover the most popular places to visit in Upper East Side

Harley-Davidson Museum showing 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 interior views and zoo animals 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
Milwaukee Art Museum

Milwaukee Art Museum

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

Milwaukee Art Museum

Things to do

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

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

$9
per adult
80% of travellers recommend
The Grand Walk: A Self-Guided Audio Tour through Milwaukee
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

$32
per adult
Milwaukee Morbid Mirrorlight Ghost Tours
Milwaukee : Best Street Food Private Tour With A Local Guide

Milwaukee Best Street Food Tour With A Local Guide

$107
per adult
Milwaukee Best Street Food Tour With A Local Guide
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.