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
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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

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
Fully refundableReserve now, pay when you stay
The price is AU$282 per night from 19 Oct to 20 Oct
AU$282
19 Oct - 20 Oct
includes taxes & fees
8/10 Very Good! (3,016 reviews)
"Have stayed here a couple of times and excellent service both times. The only issue we had both times is with the pool towels. They are not restocked enough. I went first thing yesterday morning and there were no towels, my daughters went in evening one night and no towels."

Reviewed on 29 Sept 2025

Wyndham Grand Pittsburgh Downtown
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
453 Boulevard of the Allies, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is AU$201 per night from 30 Oct to 31 Oct
AU$201
30 Oct - 31 Oct
includes taxes & fees
8.4/10 Very Good! (1,363 reviews)
"We have stayed at The Joinery many times. All of the staff is so friendly and accommodating. The hotel is so clean as well as all of the rooms. The hotel is centrally located and in walking distance of many places downtown and the valet service is great."

Reviewed on 30 Sept 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton
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$317 per night from 30 Oct to 31 Oct
AU$317
30 Oct - 31 Oct
includes taxes & fees
9/10 Wonderful! (1,692 reviews)
"Considering the age of the hotel everything was very well maintained. The lobbies were beautifully adorned with chandeliers and marble. The room was large, clean and comfortable."

Reviewed on 30 Sept 2025

Omni William Penn Hotel
See all 1,724 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.

Activities

Step into the shadows and discover the haunting tales of our city's past.

Pittsburgh Ghosts Steel City Haunted Tour

AU$48
per adult
100% of travellers recommend
Pittsburgh Ghosts Steel City Haunted Tour
Learning about history + architecture + art

Best of the Burgh Walking Tour of Pittsburgh

AU$49
per adult
100% of travellers recommend
Best of the Burgh Walking Tour of Pittsburgh
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

AU$20
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
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.