Shadyside Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
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.
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 Acrisure Stadium and PNC Park. Getting around the area on the metro is easy if you take a ride at North Side Station.
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.
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 Senator John Heinz Regional History Centre or Ohio River Valley.
North Side
1 out of top 10 points of interest in this area
While you're in North Side, take in top sights like Acrisure Stadium or PNC Park, and hop on the metro to see more of the city at North Side Station or Allegheny Station.
Our pick of the best Shadyside Hotel Deals
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
NZ$246
12 Oct - 13 Oct
includes taxes & fees
8.4/10 Very good! (3,797 reviews)
"No USB outlets in rooms, expensive breakfast, Hallways look old and dingy,Expensive valet, problems with wall mounted with Ac at various times, Rooms reflect older hotels from many years ago with scratched up furniture.Bright spot is best view river side of the hotel in Pittsburgh"
Reviewed on 20 Sept 2026
Pittsburgh Marriott City Center
112 Washington Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
NZ$303
16 Oct - 17 Oct
includes taxes & fees
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
NZ$267
5 Oct - 6 Oct
includes taxes & fees
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.
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.
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.
Activities
Pittsburgh: Museum of Illusions Entrance Ticket
NZ$49
per adult
94% of travellers recommend
Best of the Burgh Walking Tour of Pittsburgh
NZ$54
per adult
100% of travellers recommend
Pittsburgh: Best of the Burgh History and Architecture Tour
NZ$54
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.