Shadyside Vacations from $296
Book a Hotel + Flight or Car together to unlock savings
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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.
Seven Springs Resort Properties
Save 100% on your flight
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Pittsburgh (PIT)
8/10 Very Good! (12 reviews)
The condo was perfect for our family. 3 bedrooms, 3 bathrooms and a kitchen with plenty of pots/pans/utensils to cook your own meals. Its a great place to get away with the family in nature, play board games and just spend time together.
Reviewed on Jun 28, 2025
Hilton Garden Inn Pittsburgh University Place
Central Oakland
per person
Aug 26 - Aug 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
8.8/10 Excellent! (1,001 reviews)
Stayed here for a couple of nights while going to a Pirates game. It was fine. Clean, nice staff and close to some decent food. It’s a bit outdated and price for valet parking was outrageous at nearly $40 per night with tax. You cannot park yourself unless you park on the street and good luck with that.
Reviewed on Jun 30, 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
$132 nightly
The price is $150 total per night from Jul 14 to Jul 15
$150 total
Jul 14 - Jul 15
Total includes taxes and fees
8/10 Very Good! (2,919 reviews)
"."
Reviewed on Jun 29, 2025
La Quinta Inn by Wyndham Pittsburgh Airport
8507 University Blvd, Coraopolis, PA
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $96 total per night from Jul 7 to Jul 8
$96 total
Jul 7 - Jul 8
Total includes taxes and fees
7.8/10 Good! (1,969 reviews)
"Everything was as advertised"
Reviewed on Jun 26, 2025
Drury Plaza Hotel Pittsburgh Downtown
745 Grant Street, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $136 total per night from Jul 13 to Jul 14
$136 total
Jul 13 - Jul 14
Total includes taxes and fees
9.4/10 Exceptional! (1,892 reviews)
"Great stay, and lots of perks for not being a member of this hotel brand."
Reviewed on Jun 30, 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
Private City Kickstart Tour: Tokyo
$134
per adult
100% of travellers recommend
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
Pittsburgh: Beauty of the Burgh Bike Tour
$59
per adult
100% of travellers recommend
Explore a world of travel with Expedia
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
- Hotels near Chatham University
- Hotels near Squirrel Hill
- Hotels near Friendship
- Luxury Hotels in Squirrel Hill
- Boutique Hotels in Squirrel Hill
- 5 Star Hotels in Squirrel Hill
- Casino Hotels in Squirrel Hill
- 4 Star Hotels in Squirrel Hill
- Historic Hotels in Squirrel Hill
- Romantic Hotels in Squirrel Hill
- 3 Star Hotels in Squirrel Hill
- Hotels near Downtown Pittsburgh
- Hotels near University of Pittsburgh
- Hotels near Carnegie Museum of Art
- Hotels near Pittsburgh Center for the Arts
- Hotels near Heinz Memorial Chapel
- Hotels near Carnegie Museum of Natural History
- Hotels near North Oakland
- Hotels near Pittsburgh Glass Center
- Hotels near Kelly Strayhorn Theater
- Hotels near East Liberty
- Hotels near Bloomfield
- Hotels near Carnegie Library of Pittsburgh
- Cheap Hotels in East Liberty
- Hotels near Temple Sinai
- 4 Star Hotels in Bloomfield
- Extended Stay Hotels in Bloomfield
- Casino Hotels in Bloomfield
- Pet-friendly Hotels in Bloomfield
- Hotels with a Pool in Bloomfield
- Marriott Hotels & Resorts in East Liberty
- Hotels with an Indoor Pool in Bloomfield
- Hotels with Free Breakfast in Bloomfield
- Hotel Wedding Venues Hotels in Bloomfield
- Pet-friendly Hotels in East Liberty
- Extended Stay America Hotels in East Liberty
- Boutique Hotels in East Liberty
- Hotels with Restaurants in East Liberty
- Hotel Wedding Venues Hotels in East Liberty
- 3 Star Hotels in East Liberty
- Non-Smoking Hotels in East Liberty
- 4 Star Hotels in East Liberty
- Family Hotels in East Liberty
- Hotels with Connecting Rooms in East Liberty
- Historic Hotels in East Liberty
- Hotels near Cathedral of Learning
- Hotels near Phipps Conservatory
- Hotels near Bakery Square
- 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.