Shadyside Vacations

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    Save up to NT$5,067 when you book a flight and hotel together*

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Where to stay in Shadyside

Find the best Shadyside areas and neighborhoods for the activities you enjoy most. Learn more about Shadyside
Downtown Pittsburgh which includes a bridge and a river or creek

Downtown Pittsburgh

2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)

Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.

Find hotels in Downtown Pittsburgh

Shadyside Hotel Deals

Mansions on Fifth Hotel

Mansions on Fifth Hotel

4 out of 5
5105 Fifth Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (999 reviews)
Fantastic property in a great location...if you like historical buildings and old school hotels then this one will not disappoint...

Reviewed on 2026/1/25

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Mansions on Fifth Hotel
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 NT$4,019 per night from Mar 18 to Mar 19
NT$4,019
NT$4,581 total
Mar 18 - Mar 19
includes taxes & fees
8.2/10 Very Good! (3,405 reviews)
Nice

Reviewed on 2026/2/10

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 NT$5,005 per night from Feb 20 to Feb 21
NT$5,005
NT$5,706 total
Feb 20 - Feb 21
includes taxes & fees
9/10 Wonderful! (1,937 reviews)
Stayed here multiple times and never disappointed. Clean, safe, and great staff.

Reviewed on 2026/2/7

Omni William Penn Hotel
See all 1,933 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 vacation package cost?
From just . Yes, you read that correctly. Our Shadyside vacation packages are the quickest way to make your dollars go much further. Combine your favorite hotels, flights and car rentals and explore this lively destination.
How do I get a cheap travel package to Shadyside?
Booking a Shadyside vacation 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 traveler favorites.
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 favorites among many savvy travelers.
How far in advance should I book my Shadyside vacation?
It can be tricky to know exactly when the best time is to book your Shadyside vacation. 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 favorite 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 vacation is only a few clicks away.
Can I choose my airline with a Shadyside Expedia vacation 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 vacation package?
We totally get that life can throw you the odd curveball. If you've booked a Shadyside vacation 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.

Discover the most popular places to visit in Shadyside

PNC Park showing a city

PNC Park

Root for the Pittsburgh Pirates at this iconic stadium, which blends a timeless ballpark atmosphere with modern amenities.

PNC Park
Mario Lemieux statue

PPG Paints Arena

Catch an event at PPG Paints Arena during your trip to Pittsburgh. Experience the acclaimed theater scene or attend a sporting event in this vibrant area.

PPG Paints Arena
University of Pittsburgh in Pittsburgh, PA

University of Pittsburgh

Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

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