Shadyside Vacations from $625
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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
$625
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
8/10 Very Good! (325 reviews)
Apartment was on a very busy street next to a 24 hr store and had a lot of people just standing around on the corner all day and night. Not the safest spot after dark. You could hear everything on the street all night, so hard to fall asleep. Building and hall smelled like weed but the apartment was fine. I texted the number that gave me the code and they said they would check the floor, address the issue and keep me posted. Never heard back from them. No thrills but didn’t expect any given the cost. Parking was supposed to be $25/day with in and out privileges in the assigned parking lot but there was never an attendant there so no in and out and charged $30/day.
Reviewed on Sep 20, 2026
The Inn on Negley
Shadyside
$665
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
10/10 Exceptional! (221 reviews)
So clean! A beautiful house and an amazing breakfast! Staff were wonderful. Short walk to shops and restaurants. Highly recommended.
Reviewed on Sep 23, 2026
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
$741
per person
Dec 5 - Dec 7
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.6/10 Excellent! (1,004 reviews)
I would highly recommend! We spent our 2nd anniversary there for the Steelers game and when we arrived to our room they were so kind to leave us some goodies and a little note to congratulate us! It was a very clean hotel and room! Staffing very kind! Will be staying again for sure!
Reviewed on Sep 14, 2026
Oakmont Inn
Plum
$843
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Pittsburgh (PIT)
10/10 Exceptional! (38 reviews)
From the minute we arrived to the minute we checked out, an amazing stay, very clean, beds comfortable, convenient location. Great space downstairs for family, gym, and breakfast each morning was wonderful. Will stay here again and recommend to friends and family
Reviewed on Jul 5, 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.
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
Oct 12 - Oct 13
Total with taxes and fees
8.4/10 Very Good! (3,784 reviews)
"Valet parking is limited during concerts so be prepared to park your own car in another garage and walk a little ways to the hotel"
Reviewed on Sep 24, 2026
Pittsburgh Marriott City Center
112 Washington Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
$152 nightly
$173 total
Oct 16 - Oct 17
Total with taxes and fees
DoubleTree by Hilton Pittsburgh - Green Tree
500 Mansfield Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$106 nightly
$121 total
Oct 25 - Oct 26
Total with taxes and fees
8.8/10 Excellent! (1,214 reviews)
"The internet was out the whole weekend of my stay from the time of check in Friday 4pm-11am check out on Sunday very inconvenient and if you can help it steer clear of Ms. R that works the front desk her customer service skills are lacking 😓😭"
Reviewed on Sep 23, 2026
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 Pirates Baseball Game at PNC Park
$47
per adult
100% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
$29
per adult
86% 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.