Upper East Side Vacations from $543

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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.
Hilton Garden Inn Milwaukee Airport

Hilton Garden Inn Milwaukee Airport

3 out of 5
Price was $728, price is now $543 per person
$543
per person
Nov 19 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Milwaukee (MKE)
9.2/10 Wonderful! (1,001 reviews)
Beds were so comfortable. Rooms spacious and clean. All of the workers were super nice! Definetly would stay again.

Reviewed on Aug 10, 2025

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Save 100% on your flight
Price was $1,043, price is now $745 per person
$745
per person
Nov 19 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Milwaukee (MKE)
9/10 Wonderful! (1,333 reviews)
I love the casino and the room. Both were very clean. The sportsbook shuttle ti the games is very unorganized. The master switch in my room would go on by itself and wake me up a few times

Reviewed on Aug 29, 2025

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Save 100% on your flight
Price was $940, price is now $673 per person
$673
per person
Nov 19 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Milwaukee (MKE)
9.2/10 Wonderful! (1,008 reviews)
Always an enjoyable stay @The Ironhorse.. Beds are uber comfortable , love the pillows !

Reviewed on Aug 27, 2025

The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
Westown
Save 100% on your flight
Price was $940, price is now $683 per person
$683
per person
Nov 19 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Milwaukee (MKE)
9.4/10 Exceptional! (1,012 reviews)
Clean room and Friendly staff

Reviewed on Aug 28, 2025

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was $974, price is now $731 per person
$731
per person
Nov 19 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Milwaukee (MKE)
9.6/10 Exceptional! (1,707 reviews)
Historic, beautiful architecture and stunning interiors in the building. Also food and bar options.

Reviewed on Aug 30, 2025

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
$205 nightly
The price is $242 total per night from Sep 21 to Sep 22
$242 total
Sep 21 - Sep 22
Total with taxes and fees
9.4/10 Exceptional! (1,654 reviews)
"This is a great property to stay at, the hotel is very nice with lots of artwork and ambience. I highly recommend if you’re ever in Milwaukee.."

Reviewed on Aug 23, 2025

The Pfister Hotel
Sonesta Milwaukee West Wauwatosa

Sonesta Milwaukee West Wauwatosa

3.5 out of 5
10499 W Innovation Dr, Milwaukee, WI
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $107 total per night from Sep 7 to Sep 8
$107 total
Sep 7 - Sep 8
Total with taxes and fees
Sonesta Milwaukee West Wauwatosa
AmericInn by Wyndham Glendale/Milwaukee

AmericInn by Wyndham Glendale/Milwaukee

2.5 out of 5
5110 N Port Washington Rd, (772), Milwaukee, WI
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $78 total per night from Sep 14 to Sep 15
$78 total
Sep 14 - Sep 15
Total with taxes and fees
7.6/10 Good! (1,014 reviews)
"Good breakfast. Convenient to where we were visiting."

Reviewed on Aug 24, 2025

AmericInn by Wyndham Glendale/Milwaukee
See all 1,156 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

4.5/5(337 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 County Zoo featuring interior views and zoo animals as well as a small group of people

Milwaukee County Zoo

4.5/5(217 reviews)

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

4.5/5(400 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

Things to do

At the Pabst, Captain Frederick Pabst can been seen smoking backstage on a ghost tour of Milwaukee with Brew City Ghosts

Brew City Ghosts: Macabre Milwaukee By US Ghost Adventures

$26
per adult
Brew City Ghosts: Macabre Milwaukee By US Ghost Adventures
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
Kayaks Rentals Everyday

Milwaukee Kayak Rental

$55
per adult
Milwaukee Kayak Rental
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.