South Side Vacations from $237
Book a Hotel + Flight or Car together to unlock savings
Your South Side Vacation
Well known for its walking and culture, South Side draws visitors from near and far. Let our South Side vacation packages give you a peek into this neighborhood and everything it has to offer. Eager to head out and see the sights during your trip to South Side? Be sure to stop by nearby attractions like Acrisure Stadium, University of Pittsburgh and PNC Park. Don't just dream it — do it! Book your ideal South Side vacation with Expedia and get to where you're going your way.
The Latest South Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh
Downtown Pittsburgh
Price was $311, price is now $237 per person
$237
per person
Jan 8 - Jan 10
found 2 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
7.8/10 Good! (194 reviews)
Communication was perfect between myself and the property. Clean and nice for a night stay in the Pittsburgh!
Reviewed on Oct 13, 2025
Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
Price was $341, price is now $256 per person
$256
per person
Jan 8 - Jan 10
found 2 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
7.8/10 Good! (26 reviews)
Very very clean. Great walkable location
Reviewed on Oct 29, 2025
Hilltop Inn
Save 100% on your flight
Price was $683, price is now $552 per person
$552
per person
Jan 16 - Jan 18
found 1 day ago
Roundtrip flight included
New York (NYC) to Pittsburgh (PIT)
5/10 (1,007 reviews)
Price/ value..... Very run down & resistant to ALL IMPROVEMENTS.
$ is king & Queen, here
Reviewed on Oct 31, 2025
Melwood Suites Unit 107 Studio
Oakland
Price was $313, price is now $256 per person
$256
per person
Jan 8 - Jan 10
found 2 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
9.6/10 Exceptional! (35 reviews)
Elegant place with everything organized extremely well!
Reviewed on Jul 25, 2025
Wyndham Grand Pittsburgh Downtown
Downtown Pittsburgh
Price was $528, price is now $433 per person
$433
per person
Jan 22 - Jan 24
found 21 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Pittsburgh (PIT)
8.2/10 Very Good! (3,079 reviews)
Clean, friendly and convenient location.
Reviewed on Nov 3, 2025
Discover the most popular places to visit in South Side
PNC Park
4.5/5(780 reviews)
Root for the Pittsburgh Pirates at this iconic stadium, which blends a timeless ballpark atmosphere with modern amenities.
University of Pittsburgh
4.5/5(843 reviews)
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the fascinating museums in this vibrant area.
Acrisure Stadium
4.5/5(998 reviews)
Giant ketchup bottles tilt onto the scoreboard to celebrate touchdowns in this innovative riverside football arena at the heart of Pittsburgh sports.
What to do in South Side
Pittsburgh Pirates Baseball Game at PNC Park
$27
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
Echoes from the Iron Forge: Pittsburgh Phantoms Ghost Tour
$26
per adult
100% of travellers recommend
South Side Hotel Deals
Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG
20 S 10th St, Pittsburgh, PA
Fully refundable
$83 nightly
The price is $95 total per night from Nov 23 to Nov 24
$95 total
Nov 23 - Nov 24
Total with taxes and fees
7/10 Good! (1,031 reviews)
Very close to the attractions on East Carson St.
Reviewed on Nov 2, 2025
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $119 total per night from Dec 4 to Dec 5
$119 total
Dec 4 - Dec 5
Total with taxes and fees
8/10 Very Good! (3,088 reviews)
clean
Reviewed on Nov 1, 2025
Omni William Penn Hotel
530 William Penn Place, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $191 total per night from Nov 16 to Nov 17
$191 total
Nov 16 - Nov 17
Total with taxes and fees
9/10 Wonderful! (1,744 reviews)
Only reason it wasn’t a Five Star Rooms were not available At 4 pm Hour after check in Love the Hotel, great place
Reviewed on Oct 31, 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.
Find the Best South Side Vacation Packages
South Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Pittsburgh Intl. Airport (PIT) |
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- Pittsburgh Vacations
- Visit South Side Slopes
- Market Square
- Visit Pittsburgh
- Duquesne University
- University of Pittsburgh
- Visit South Side Flats
- PPG Paints Arena
- Visit Bluff
- U.S. Steel Tower
- Allegheny County Courthouse
- Roberto Clemente Bridge
- The Nationality Rooms
- Petersen Events Center
- Monongahela Incline
- Station Square
- Downtown Pittsburgh Vacations
- University of Pittsburgh Medical Center
- Senator John Heinz Regional History Centre
- Cathedral of Learning
- Western Pennsylvania Sports Museum
- Where to stay in Pittsburgh
- Benedum Center
- David L Lawrence Convention Center
- Soldiers and Sailors Memorial Hall and Museum
- Carnegie Museum of Natural History
- Phipps Conservatory
- Visit Downtown Pittsburgh
- Point State Park
- Cabaret at Theatre Square
- Visit Allegheny County
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.