Shadyside Vacations from $253
Book a Hotel + Flight or Car together to unlock savings
Photo by Hayley Gallagher
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.
DoubleTree by Hilton Pittsburgh - Green Tree
Price was $343, price is now $253 per person
$253
per person
Feb 21 - Feb 24
found 11 hours ago
Roundtrip flight included
Chicago (CHI) to Pittsburgh (PIT)
8.2/10 Very Good! (1,004 reviews)
No microwave in the room. Thought that was standard these days. Shower was just a trickle.
Reviewed on Dec 10, 2025
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
Price was $408, price is now $279 per person
$279
per person
Feb 21 - Feb 24
found 11 hours ago
Roundtrip flight included
Chicago (CHI) to Pittsburgh (PIT)
8.4/10 Very Good! (1,385 reviews)
clean and comfortable!
Reviewed on Dec 8, 2025
Hilton Garden Inn Pittsburgh Downtown
Downtown Pittsburgh
Price was $402, price is now $305 per person
$305
per person
Feb 21 - Feb 24
found 11 hours ago
Roundtrip flight included
Chicago (CHI) to Pittsburgh (PIT)
9/10 Wonderful! (1,151 reviews)
The hotel lobby is in serious need of a new,clean,unfrayed sofa...the one c there now is dated,ratty looking, frayed,and dirty.Not a good first look.
Reviewed on Dec 11, 2025
The Landing Hotel at Rivers Casino
North Side
Price was $793, price is now $601 per person
$601
per person
Jan 12 - Jan 17
found 13 hours ago
Roundtrip flight included
Minneapolis (MSP) to Pittsburgh (PIT)
9.4/10 Exceptional! (1,211 reviews)
Breakfast was a highlight and management, especially Connie and Dravin made the trip pleasant.
Reviewed on Dec 9, 2025
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
4.5/5(2,251 area reviews)
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
$120 nightly
The price is $137 total per night from Dec 28 to Dec 29
$137 total
Dec 28 - Dec 29
Total with taxes and fees
8.2/10 Very Good! (3,228 reviews)
The hotel was immaculate. The view was the greatest view. You can see so much then they had a SKY lounge room that you can just look out of the windows and see everything hotel was very clean very well. Kept everyone on the staff was very polite. I would definitely stay there again. They even allowed ...
Reviewed on Dec 8, 2025
Joinery Hotel Pittsburgh, Curio Collection by Hilton
453 Boulevard of the Allies Pittsburgh PA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $123 total per night from Dec 21 to Dec 22
$123 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (1,405 reviews)
Customer Service
Reviewed on Dec 1, 2025
Omni William Penn Hotel
530 William Penn Place Pittsburgh PA
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $177 total per night from Dec 21 to Dec 22
$177 total
Dec 21 - Dec 22
Total with taxes and fees
9/10 Wonderful! (1,813 reviews)
Wonderful staff and accommodations..great location especially if you plan on attending something at PPG arena
Reviewed on Dec 9, 2025
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.
Discover the most popular places to visit in Shadyside
UPMC Shadyside
4.5/5(8 reviews)
Though UPMC Shadyside might be what brings you to town, perhaps you'll have a chance to explore more of Pittsburgh while you are here.
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.
Things to do
Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena
$72
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
Pittsburgh Steelers Football Game at Acrisure Stadium
$452
per adult
Explore a world of travel with Expedia
- Pittsburgh Hotels
- Hotels near UPMC Shadyside
- Hotels near Carnegie Mellon University
- Hotels near Walnut Street
- Hotels near Gallerie CHIZ
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- Hotels near Cathedral of Learning
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- Hotels near Soldiers and Sailors Memorial Hall and Museum
- Hotels near Oakland
- Hotels near Mellon Park
- Hotels near Schenley Park
- Hotels near Manor Theatre
- Hotels near Central Oakland
- Walnut Street
- Carnegie Mellon University
- Chatham University
- Hunt Institute for Botanical Documentation
- Carnegie Museum of Natural History
- Carnegie Museum of Art
- Cathedral of Learning
- Heinz Memorial Chapel
- Kelly Strayhorn Theater
- University of Pittsburgh
- Phipps Conservatory
- Temple Sinai
- Schenley Park
- Soldiers and Sailors Memorial Hall and Museum
- Visit Squirrel Hill
- Bakery Square
- Manor Theatre
- University of Pittsburgh Medical Center
- The Nationality Rooms
- Visit Bloomfield
- Visit East Liberty
- Homewood Cemetery
- Petersen Events Center
- Visit Oakland
- Car rentals near Pittsburgh
- Car rentals near UPMC Shadyside
- Car rentals near Gallerie CHIZ
- Car rentals near Carnegie Mellon University
- Premium Car Rentals near Carnegie Mellon University
- Car rentals near Squirrel Hill
- Enterprise Rental Cars in Squirrel Hill
- Premium Car Rentals in Squirrel Hill
- Car rentals near Heinz Memorial Chapel
- Car rentals near East Liberty
- Car rentals near Temple Sinai
- Hertz Rental Cars in East Liberty
- Car rentals near Bloomfield
- Budget Rental Cars in East Liberty
- Car rentals near Phipps Conservatory
- Car rentals near Bakery Square
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.