Shadyside Holidays

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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
A yellow bridge over a river with a cityscape in the background.

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.

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A yellow bridge over a river, a weeping willow tree, and a modern building with glass windows.

North Shore

2 out of top 10 points of interest in this area

Visitors often come to North Shore for its stunning river views, but many stay to explore sights like PNC Park and Acrisure Stadium. Getting around the area on the metro is easy if you take a ride at North Side Station.

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The Mellon Institute at Carnegie Mellon University with classical columns and a Gothic cathedral in the background.

Oakland

1 out of top 10 points of interest in this area

Oakland is known for its ample dining options, and you can make a stop by Petersen Events Center and Carnegie Museum of Natural History while in the area.

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A street with a Starbucks and a plaza with colorful steps.

Strip District

Strip District is popular for its abundant dining options, and if you're looking for more to see and do, you might think about a trip to The Terminal or Senator John Heinz Regional History Centre.

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A river with a bridge, a van on the road, and buildings in the background.

Mount Washington

Spend some time visiting places like Ohio River Valley while getting to know Mount Washington, and be sure to check out the abundant dining options. You can hop aboard the metro at South Hills Junction Station or Palm Garden Station to see more of the area.

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Top hotels in Shadyside

Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
S$180
22 Oct - 23 Oct
includes taxes & fees
8.4/10 Very good! (3,784 reviews)
"Valet parking is limited during concerts so be prepared to park your own car in another garage and walk a little ways to the hotel"

Reviewed on 24 Sept, 2026

Wyndham Grand Pittsburgh Downtown
Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

112 Washington Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
S$221
22 Oct - 23 Oct
includes taxes & fees
Pittsburgh Marriott City Center
DoubleTree by Hilton Pittsburgh - Green Tree

DoubleTree by Hilton Pittsburgh - Green Tree

500 Mansfield Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
S$158
25 Oct - 26 Oct
includes taxes & fees
8.8/10 Excellent! (1,214 reviews)
"The internet was out the whole weekend of my stay from the time of check in Friday 4pm-11am check out on Sunday very inconvenient and if you can help it steer clear of Ms. R that works the front desk her customer service skills are lacking 😓😭"

Reviewed on 23 Sept, 2026

DoubleTree by Hilton Pittsburgh - Green Tree
See all 2,030 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.

Stay near popular Shadyside attractions

Walnut Street

During your trip to Pittsburgh, you can search for that perfect souvenir at Walnut Street. Savour the area's restaurants and bars.
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Gallerie CHIZ

You can spend an afternoon browsing the exhibits at Gallerie CHIZ in Pittsburgh. Amble around this vibrant area's riverfront or experience its acclaimed theatre scene.
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Mellon Park Tennis Center

Catch an event at Mellon Park Tennis Center during your trip to Pittsburgh. Visit the area's shops or simply enjoy its restaurants.
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Things to do

Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

S$37
per adult
94% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

S$17
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
Make new friends as you learn the exciting history of whiskey in Pittsburgh

Whiskey Rebellion & Prohibition Tour

S$62
per adult
100% of travellers recommend
Whiskey Rebellion & Prohibition Tour
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.