Shadyside Vacation Packages
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Top Holiday Package Deals in Shadyside
Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Pittsburgh University-Oakland by IHG
Oakland
CA $1,269
per person
Nov 26 - Nov 29
found 1 hour ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,007 reviews)
Close to medical facilities at UPMC, this hotel was perfect for us. Zoe was so helpful and welcoming upon check-in. It's a newer building and everything was clean and well-lighted. Our room was more like a suite with two televisions, separate couch and seating area for one of them. Bed was comfortable (A tad softer than we prefer) with very nice linens and four pillows. Bath towels were excellent quality, as were the toiletries in pump dispensers. Shower had hand-held hose option with good pressure. No carpet in room, thank goodness, a few well-placed area rugs. Restaurant and bar on site are always nice (kitchen open until 9 pm, bar until 10 pm with menus that cover all the bases at reasonable prices). Adjacent parking was $22. Note: there is a microwave in the lobby "market", none in the rooms. Keurig coffee maker had tea and coffee pods. Ear plugs provided for those who needed them (we did not). Parkway traffic sounds not an issue for us, but light sleepers should ask for river-side room. TV was challenging: no option to choose a specific channel, volume control took time to figure how to use. We would stay here again and recommend without hesitation.
Reviewed on Oct 14, 2026
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
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.
North Shore
2 out of top 10 points of interest in this area
Heinz Field, PNC Park, and The Andy Warhol Museum await in this vibrant area, connected to Downtown Pittsburgh by the iconic Roberto Clemente, Andy Warhol, and Rachel Carson Bridges. Enjoy easy access to two light rail stations.
Oakland
1 out of top 10 points of interest in this area
Academic and healthcare hub, Oakland boasts museums, shopping venues, and diverse dining options along Forbes and Fifth Avenue. Explore historic districts and easily navigate the area via the distinctive city steps and public transportation.
Strip District
Brimming with specialty shops, unique boutiques, and ethnic food purveyors, the Strip District offers a lively atmosphere with art studios, antique dealers, and the historic St. Stanislaus Kostka Church. Enjoy open-air markets and vibrant nightlife during summer months.
North Side
1 out of top 10 points of interest in this area
If you're spending time in North Side, check out sights like PNC Park or Acrisure Stadium and hop on the metro to see more the city at North Side Station or Allegheny Station.
Shadyside Hotel Deals
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $176
CA $200 total
Nov 2 - Nov 3
includes taxes & fees
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $159
CA $181 total
Nov 15 - Nov 16
includes taxes & fees
9.4/10 Exceptional! (2,449 reviews)
"Clean room. Good free breakfast. Staff is very helpful."
Reviewed on Oct 16, 2026
DoubleTree by Hilton Pittsburgh - Green Tree
500 Mansfield Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $147
CA $168 total
Nov 8 - Nov 9
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 vacation package cost?
From just CA $1,104. 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.
Stay near popular Shadyside attractions
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.
Gallerie CHIZ
You can spend an afternoon studying the exhibits at Gallerie CHIZ during your trip to Pittsburgh. Amble around this vibrant area's riverfront or experience its acclaimed theater scene.
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.
Things to do
Pittsburgh: Museum of Illusions Entrance Ticket
CA $41
per adult
86% of travellers recommend
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
CA $18
per adult
Pittsburgh Steelers Football Game at Acrisure Stadium
CA $428
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.