Shadyside Vacations from $299
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Your Shadyside Vacation
Booking a Shadyside vacation package is a wonderful way to get to know the ins and outs of this unique neighborhood. From its renowned sites to its lesser-known treasures, a world of discovery is waiting. Start your trip to Shadyside by checking out nearby attractions such as University of Pittsburgh, Carnegie Mellon University and PPG Paints Arena. Whatever your travel plans or budget, booking your perfect Shadyside vacation has never been easier with Expedia.
The Latest Shadyside Vacation Packages
DoubleTree by Hilton Pittsburgh - Cranberry
Reviewed on Oct 18, 2026
Where to stay in Shadyside
Downtown Pittsburgh
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
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
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.
North Side
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.
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.
Shadyside Hotel Deals
Mansions on Fifth Hotel
Wyndham Grand Pittsburgh Downtown
"Beautiful hotel. Was not expecting the room to be small with a king bed, but I made it work. The bed was not comfortable. Mattress appeared to be sunken in some spots. It would also have been nice to have a SMART television so that I could stream programs."
Reviewed on Oct 20, 2026
The Landing Hotel at Rivers Casino
Stay near popular Shadyside attractions
Walnut Street
Gallerie CHIZ
Mellon Park Tennis Center
Things to do
Pittsburgh: Museum of Illusions Entrance Ticket
Black & Gold Pittsburgh History Tour for Sports Fans
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
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- Visit Pittsburgh
- Byham Theater
- Lighthouse ArtSpace Pittsburgh
- Grandview Overlook
- Visit Downtown Pittsburgh
- Roberto Clemente Bridge
- North Shore Vacations
- Strip District Vacations
- Walnut Street
- Andy Warhol Museum
- Acrisure Stadium
- Senator John Heinz Regional History Centre
- Photo Antiquities Museum of Photographic History
- Carnegie Science Center
- Monongahela Incline
- Carnegie Museum of Art
- Carnegie Library of Pittsburgh
- National Aviary
- U.s. Steel Tower
- Point State Park
- Hunt Institute for Botanical Documentation
- Manor Theatre
- Rachel Carson Bridge
- Duquesne Incline
- Carnegie Museum of Natural History
- Children's Museum of Pittsburgh
- Where to stay in Pittsburgh
- University of Pittsburgh
- Andy Warhol Bridge
- Schenley Park
- Kennywood
- Heinz Memorial Chapel
- Market Square
- Phipps Conservatory
- Cathedral of Learning
- Temple Sinai
- Carnegie Mellon University
- Pnc Park
- Soldiers and Sailors Memorial Hall and Museum
- Pittsburgh Vacations