Upper East Side Holidays & Package Deals

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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

A river with a city skyline, including a tall building with a pointed roof, and a park with yellow trees.

Downtown Milwaukee

Lake Michigan and Cathedral Square 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.

A river with buildings reflecting on the water, a bridge, and a tall building with a green roof.

West Allis

West Allis is noteworthy for its restaurants, and you can make a stop at top attractions like Milwaukee Mile Speedway and Wisconsin State Fair Park.

A waterfront cityscape at dusk with a calm river reflecting buildings and a bridge.

Wauwatosa

1 out of top 10 points of interest in this area

Travellers come to Wauwatosa for its abundant dining options, and you can see top attractions like Mayfair Mall and The Mayfair Collection while you're in town.

A river with boats, a marina, and historic buildings along the waterfront.

Historic Third Ward

Experience Milwaukee’s hot spot for art and fashion when you check out the dynamic boutiques, restaurants, theaters and galleries that fill this exciting district.

A boat named "Vista King" on a river with a building featuring fish decorations in the background.

Westown

2 out of top 10 points of interest in this area

While visiting Westown, you might make a stop by sights like Miller High Life Theatre and UW–Milwaukee Panther Arena.

Our pick of the best Upper East Side Hotel Deals

Hyatt Regency Milwaukee

333 W Kilbourn Ave Milwaukee WI

Fully refundableReserve now, pay when you stay

AU$157

1 Nov - 2 Nov

includes taxes & fees

8.6/10 Excellent! (1,533 reviews)

"Just ok. We were in town a couple of days before at a more "affordable" hotel and I would choose that one again in the future."

Reviewed on 12 Oct 2026

Sheraton Milwaukee Brookfield Hotel

375 S Moorland Rd Brookfield WI

Fully refundableReserve now, pay when you stay

AU$105

1 Nov - 2 Nov

includes taxes & fees

8.4/10 Very good! (1,242 reviews)

"The bathrooms need updating. Rooms were clean but also need updating. We had broken closet doors. It was quiet and staff were friendly!"

Reviewed on 12 Oct 2026

Drury Plaza Hotel Milwaukee Downtown

700 N. Water Street Milwaukee WI

Fully refundableReserve now, pay when you stay

AU$201

1 Nov - 2 Nov

includes taxes & fees

9.6/10 Exceptional! (2,418 reviews)

"Room was clean and breakfast was hot."

Reviewed on 12 Oct 2026

See all 1,135 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 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.

Stay near popular Upper East Side attractions

Miramar Theatre

You can make plans for a show at Miramar Theatre during your trip to Milwaukee.

See properties

Activities

Milwaukee Morbid Mirrorlight Ghost Tours

AU$37

per adult

Milwaukee's Riverwalk Walking Tour

AU$22

per adult

100% of travellers recommend

Skip the Line: Museum Admission Ticket - Grohmann Museum

AU$7

per adult

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.

Upper East Side Holidays

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Upper East Side Holiday

Our guide on where to stay in Upper East Side

Downtown Milwaukee

West Allis

Wauwatosa

Historic Third Ward

Westown

Our pick of the best Upper East Side Hotel Deals

Hyatt Regency Milwaukee

Sheraton Milwaukee Brookfield Hotel

Drury Plaza Hotel Milwaukee Downtown

Frequently asked questions

Stay near popular Upper East Side attractions

Miramar Theatre

Activities

Milwaukee Morbid Mirrorlight Ghost Tours

Milwaukee's Riverwalk Walking Tour

Skip the Line: Museum Admission Ticket - Grohmann Museum