Shadyside Holidays

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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 NZ$257 per night from 17 Aug to 18 Aug
NZ$257
17 Aug - 18 Aug
includes taxes & fees
8/10 Very Good! (2,966 reviews)
"queen sized beds seemed a lot smaller than a true queen size. excellent valet parking attendants. hotel restaurant hours did not meet my family's expectations."

Reviewed on 11 Aug. 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 NZ$274 per night from 27 Aug to 28 Aug
NZ$274
27 Aug - 28 Aug
includes taxes & fees
9/10 Wonderful! (1,599 reviews)
"The hotel and restaurant/bar very nice,good food, polite staff."

Reviewed on 11 Aug. 2025

Omni William Penn Hotel
Courtyard by Marriott Pittsburgh University Center

Courtyard by Marriott Pittsburgh University Center

3.5 out of 5
100 Lytton Avenue, Pittsburgh, PA
The price is NZ$249 per night from 24 Aug to 25 Aug
NZ$249
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (402 reviews)
"Great location"

Reviewed on 10 Aug. 2025

Courtyard by Marriott Pittsburgh University Center
See all 1,755 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.

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

Pittsburgh, PA: Sandcastle Waterpark Entry Ticket

Pittsburgh, PA: Sandcastle Waterpark Entry Ticket

NZ$58
per adult
Pittsburgh, PA: Sandcastle Waterpark Entry Ticket
Private Shopping Tour from Pittsburgh to Tanger Outlet Pittsburgh

Private Shopping Tour from Pittsburgh to Tanger Outlet Pittsburgh

NZ$371
per adult
Private Shopping Tour from Pittsburgh to Tanger Outlet Pittsburgh
Learning about history + architecture + art

Best of the Burgh Walking Tour of Pittsburgh

NZ$54
per adult
100% of travellers recommend
Best of the Burgh Walking Tour of Pittsburgh
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.