Shadyside Holidays

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Your Shadyside Holiday

Booking a Shadyside holiday package is a wonderful way to get to know the ins and outs of this unique neighbourhood. From its renowned sites to its lesser-known treasures, a world of discovery is waiting. Start your trip to Shadyside by checking out nearby attractions such as University of Pittsburgh, Carnegie Mellon University and PPG Paints Arena. Whatever your travel plans or budget, booking your perfect Shadyside holiday has never been easier with Expedia.

Our guide on where to stay in Shadyside

Find the best Shadyside areas and neighborhoods for the activities you enjoy most. Learn more about Shadyside
A yellow bridge over a river with a cityscape in the background.

Downtown Pittsburgh

2 out of top 10 points of interest in this area

Abundant dining options, interesting museums and live music are just a few top things to explore in Downtown Pittsburgh. A visit to PPG Paints Arena or Benedum Center might round out your trip, and you can jump aboard the metro at Wood Street Station or Steel Plaza Station to get around town.

Find hotels in Downtown Pittsburgh
A yellow bridge over a river, a weeping willow tree, and a modern building with glass windows.

North Shore

2 out of top 10 points of interest in this area

Visitors often come to North Shore for its stunning river views, but many stay to explore sights like PNC Park and Acrisure Stadium. Getting around the area on the metro is easy if you take a ride at North Side Station.

Find hotels in North Shore
The Mellon Institute at Carnegie Mellon University with classical columns and a Gothic cathedral in the background.

Oakland

1 out of top 10 points of interest in this area

Oakland is known for its ample dining options, and you can make a stop by Petersen Events Center and Carnegie Museum of Natural History while in the area.

Find hotels in Oakland
A bridge with illuminated lights reflecting on the water, a city skyline in the background, and a smokestack emitting smoke.

North Side

1 out of top 10 points of interest in this area

While you're in North Side, take in top sights like PNC Park or Acrisure Stadium, and hop on the metro to see more of the city at North Side Station or Allegheny Station.

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A river with a yellow bridge, a parking lot, and buildings along the riverbank.

Strip District

Strip District is popular for its abundant dining options, and if you're looking for more to see and do, you might think about a trip to Senator John Heinz Regional History Centre or Ohio River Valley.

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Our pick of the best Shadyside Hotel Deals

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
AU$242
15 Sept - 16 Sept
includes taxes & fees
8.4/10 Very good! (3,758 reviews)
"This hotel has the best location. Situated at the point where two rivers converge to become the Ohio. The views are striking and proximity to all the venues down town cannot be beat."

Reviewed on 31 Aug 2026

Wyndham Grand Pittsburgh Downtown
Omni William Penn Hotel

Omni William Penn Hotel

530 William Penn Place Pittsburgh PA
Fully refundableReserve now, pay when you stay
AU$328
7 Sept - 8 Sept
includes taxes & fees
Omni William Penn Hotel
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

500 Mansfield Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
AU$154
8 Sept - 9 Sept
includes taxes & fees
8.6/10 Excellent! (1,181 reviews)
"Beautiful facility, staff was extra helpful, amenities were clean and very accessible. Prime location"

Reviewed on 31 Aug 2026

DoubleTree by Hilton Pittsburgh - Green Tree
See all 2,026 properties in Shadyside
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.
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Frequently asked questions

How much does a Shadyside holiday package cost?
From just . Yes, you read that correctly. Our Shadyside holiday packages are the quickest way to make your dollars go much further. Combine your favourite hotels, flights and car rentals and explore this lively destination.
How do I get a cheap travel package to Shadyside?
Booking a Shadyside holiday package with Expedia is a great way to save. We have access to more than 550 partner airlines and 1 000 000 hotels across the globe. With such a broad range to pick from, you'll have no hassles creating your ideal escape.
Where should I stay in Shadyside?
Make sightseeing a breeze by staying someplace just a stone's throw away from Shadyside's biggest attractions. Acrisure Stadium and PNC Park are two traveller favourites.
What are the top hotels in Shadyside?
If it's your very first time in Shadyside, reserve a room at The Inn On Negley or Mansions on Fifth Hotel. Both hotels offer friendly service and are favourites among many savvy travellers.
How far in advance should I book my Shadyside holiday?
It can be tricky to know exactly when the best time is to book your Shadyside holiday. But typically the earlier you book, the better the prices. Sometimes, you can reserve your flights and hotels up to a year before departure. If you're eager to escape on a last-minute getaway, no need to worry! There are terrific bargains advertised on Expedia every day.
What does an Expedia Shadyside travel package include?
Flights, car rentals and hotels — we connect you to the best deals. All you'll have to do is pick and choose your favourite combination. After you've made your booking, you can add on the exciting stuff like experiences and tours. Our travel packages make it easy to put together an unforgettable Shadyside trip.
What should I know before booking a Shadyside travel package?
You can save big by bundling your hotels, airfares and rental cars. Once you've made your booking, add on fun stuff like tours and activities. Your next awesome holiday is only a few clicks away.
Can I choose my airline with a Shadyside Expedia holiday package?
Yes, you're in charge. We offer more than 550 airlines worldwide, so you can tailor your Shadyside escape according to your travel preferences.
If I'm not able to travel, can I cancel my Shadyside holiday package?
We totally get that life can throw you the odd curveball. If you've booked a Shadyside holiday package and have to cancel or amend it, we can help. We suggest having a look at our Customer Service Portal first for information. But in general, if you've booked your package in the last 24 hours, you may be able to amend or cancel your itinerary at no cost. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.

Stay near popular Shadyside attractions

Walnut Street

During your trip to Pittsburgh, you can search for that perfect souvenir at Walnut Street. Savour the area's restaurants and bars.
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Mellon Park Tennis Center

Catch an event at Mellon Park Tennis Center during your trip to Pittsburgh. Visit the area's shops or simply enjoy its restaurants.
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Gallerie CHIZ

You can spend an afternoon browsing the exhibits at Gallerie CHIZ in Pittsburgh. Amble around this vibrant area's riverfront or experience its acclaimed theatre scene.
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Activities

Pittsburgh Pirates Baseball Game at PNC Park

Pittsburgh Pirates Baseball Game at PNC Park

AU$66
per adult
100% of travellers recommend
Pittsburgh Pirates Baseball Game at PNC Park
This tour is the best tour for sports fans! Big fun guaranteed!

Black & Gold Pittsburgh History Tour for Sports Fans

AU$45
per adult
Black & Gold Pittsburgh History Tour for Sports Fans
Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

AU$40
per adult
94% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
See all activities in Pittsburgh
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.