Shadyside Vacations from $881
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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
Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh
Downtown Pittsburgh
$881
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Pittsburgh (PIT)
8/10 Very Good! (334 reviews)
Check in was rough online only. I couldn't reach anyone by phone, granted it was 10pm, but it took me forever to get through the process and then wait for a code to get into my room. Make sure you check in right when you get the text or email message.
Reviewed on Oct 17, 2026
Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
$1,075
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Pittsburgh (PIT)
8.8/10 Excellent! (271 reviews)
This building is absolutely beautiful. Our room was a one bedroom apartment style, very clean and modern. It was always quiet and could barely hear the outside traffic. They have an amazing coffee machine in the lobby with multiple options from espresso, hot chocolate, etc. The hotel staff went above and beyond for us. They even lent us an umbrella on a rainy day. I've stayed at a lot of places including vrbo and this was the best place I've ever stayed at.
Reviewed on Oct 18, 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
$124 nightly
$141 total
Nov 2 - Nov 3
Total with taxes and fees
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
$127 nightly
$144 total
Nov 15 - Nov 16
Total with taxes and fees
9.4/10 Exceptional! (2,451 reviews)
"Great staff great service highly satisfied"
Reviewed on Oct 18, 2026
DoubleTree by Hilton Pittsburgh - Green Tree
500 Mansfield Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$101 nightly
$115 total
Nov 8 - Nov 9
Total with taxes and 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.
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
$29
per adult
86% of travellers recommend
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
Pittsburgh: Beauty of the Burgh Bike Tour
$59
per adult
94% of travellers recommend
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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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.