Shadyside Vacations from $505
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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
$628
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8/10 Very Good! (313 reviews)
Some confusion on my end with paying the deposit, as I thought I was paying for my room a second time, but the host was quick to clear it up. Another pleasant stay at this clean and quiet property.
Reviewed on Aug 9, 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.
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.
Mount Washington
Restaurant Row and scenic leafy parks lie along the ridge of a famous hill, where George Washington mapped the terrain for the British.
Shadyside Hotel Deals
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
$124 nightly
$141 total
Sep 1 - Sep 2
Total with taxes and fees
8.2/10 Very Good! (3,728 reviews)
"Great location! Friendly staff"
Reviewed on Aug 9, 2026
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
$135 nightly
$154 total
Aug 23 - Aug 24
Total with taxes and fees
9.4/10 Exceptional! (2,125 reviews)
"Awesome place to stay, clean rooms great views"
Reviewed on Aug 8, 2026
Omni William Penn Hotel
530 William Penn Place Pittsburgh PA
Fully refundableReserve now, pay when you stay
$214 nightly
$244 total
Aug 30 - Aug 31
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.
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 studying the exhibits at Gallerie CHIZ during your trip to Pittsburgh. Amble around this vibrant area's riverfront or experience its acclaimed theater scene.
Things to do
Pittsburgh Pirates Baseball Game at PNC Park
$48
per adult
100% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
$29
per adult
90% of travellers recommend
Black & Gold Pittsburgh History Tour for Sports Fans
$33
per adult
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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.