Shadyside Vacations

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  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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

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 ￥16,873 per night from Dec 16 to Dec 17
￥16,873
￥19,236 total
Dec 16 - Dec 17
includes taxes & fees
8/10 Very Good! (3,208 reviews)
Friendly staff and great location! If needed, there’s public parking across the street, daily rates apply, but very convenient.

Reviewed on Nov 24, 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 ￥26,123 per night from Dec 16 to Dec 17
￥26,123
￥29,779 total
Dec 16 - Dec 17
includes taxes & fees
9/10 Wonderful! (1,791 reviews)
The spout on the bathtub was broken and the deposit costs were way too high. However the staff was very friendly and helpful. Everything costs extra though and is way over priced.

Reviewed on Nov 24, 2025

Omni William Penn Hotel
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 ￥15,201 per night from Dec 18 to Dec 19
￥15,201
￥17,676 total
Dec 18 - Dec 19
includes taxes & fees
8.4/10 Very Good! (1,399 reviews)
All around great stay. Beautiful building!

Reviewed on Nov 27, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,838 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

UPMC Shadyside

4.5/5(8 reviews)

Though UPMC Shadyside might be what brings you to town, perhaps you'll have a chance to explore more of Pittsburgh while you are here.

UPMC Shadyside

Walnut Street

During your trip to Pittsburgh, you can find the perfect gifts to bring home at Walnut Street. Savor the area's restaurants and bars.

Walnut Street

Things to do

Pittsburgh Pirates Baseball Game at PNC Park

Pittsburgh Pirates Baseball Game at PNC Park

￥10,151
per adult
Pittsburgh Pirates Baseball Game at PNC Park
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

￥2,059
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
Smartphone-Guided Tour of Downtown Pittsburgh Sights & Stories

Smartphone-Guided Tour of Downtown Pittsburgh Sights & Stories

￥4,329
per traveler
Smartphone-Guided Tour of Downtown Pittsburgh Sights & Stories
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.