Shadyside Vacations from $400
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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
Price was $817, price is now $621 per person
$621
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Houston (HOU) to Pittsburgh (PIT)
8/10 Very Good! (339 reviews)
The building and unit were very clean and the unit we stayed seemed newly renovated with new furniture. Very spacious and had everything we needed.
Reviewed on Oct 26, 2026
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Price was $1,096, price is now $939 per person
$939
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip flight included
Houston (HOU) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
My go to hotel when I’m in Pittsburgh. Easy to get to, parking garage right below the hotel, and great location with a ton of places within walking distance.
Reviewed on Oct 25, 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.
Shadyside Hotel Deals
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $141 total per night from Nov 9 to Nov 10
$141 total
Nov 9 - Nov 10
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
The price is $144 total per night from Nov 15 to Nov 16
$144 total
Nov 15 - Nov 16
Total with taxes and fees
DoubleTree by Hilton Pittsburgh - Green Tree
500 Mansfield Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $115 total per night from Nov 8 to Nov 9
$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
Things to do
Pittsburgh: Museum of Illusions Entrance Ticket
$29
per adult
86% of travellers recommend
Black & Gold Pittsburgh History Tour for Sports Fans
$33
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.