Shadyside Holidays

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    Save up to AU$703 when you book a flight and hotel together*
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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

Our pick of the best Shadyside Hotel Deals

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
600 Commonwealth Pl, Pittsburgh, PA
The price is AU$208 per night from 17 Aug to 18 Aug
AU$208
17 Aug - 18 Aug
includes taxes & fees
8/10 Very Good! (2,970 reviews)
"Cleanliness location"

Reviewed on 27 Jul. 2025

Wyndham Grand Pittsburgh Downtown
Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
530 William Penn Place, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is AU$250 per night from 20 Aug to 21 Aug
AU$250
20 Aug - 21 Aug
includes taxes & fees
9/10 Wonderful! (1,577 reviews)
"Historic charm in a central location, money well spent"

Reviewed on 28 Jul. 2025

Omni William Penn Hotel
The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
757 Casino Dr, Pittsburgh, PA
The price is AU$234 per night from 17 Aug to 18 Aug
AU$234
17 Aug - 18 Aug
includes taxes & fees
9.4/10 Exceptional! (882 reviews)
"Had a great view (windows not tinted/blind from below tho just fyi…) and awesome nights sleep. Breakfast was disappointing and we didn’t eat much. Overall the stay was quiet and clean. Limited tv so bring your apple box/cord."

Reviewed on 27 Jul. 2025

The Landing Hotel at Rivers Casino
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 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.

Activities

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.