South Side Vacations from $440
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
$607
per person
Nov 12 - Nov 15
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8/10 Very Good! (321 reviews)
On the edge of downtown so area was a bit gritty. Bonus points: restaurants, museums, sport venues all within walking distance. Garage right across street is super convenient with in/out privileges, nice! Room I stayed in was a bit worn, but the price was right and the host very responsive.
Reviewed on Aug 30, 2026
Stay near popular South Side attractions
Rex Theater
6.0/10 (1 review)
You can get tickets for a performance at Rex Theater on your trip to Pittsburgh. Check out the shops and top-notch restaurants in this family-friendly area.
What to do in South Side
Pittsburgh Pirates Baseball Game at PNC Park
$47
per adult
100% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
$29
per adult
94% of travellers recommend
Whiskey Rebellion & Prohibition Tour
$49
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
$88 nightly
$100 total
Sep 7 - Sep 8
Total with taxes and fees
8/10 Very Good! (1,007 reviews)
"Everyone friendly"
Reviewed on Aug 31, 2026
SpringHill Suites by Marriott Pittsburgh Southside Works
2950 S Water St Pittsburgh PA
Fully refundableReserve now, pay when you stay
$114 nightly
$129 total
Sep 6 - Sep 7
Total with taxes and fees
8.6/10 Excellent! (1,005 reviews)
"The room was very clean and the bed was very comfortable. The staff was very accommodating and helpful. Please stay here if you have the chance!"
Reviewed on Aug 30, 2026
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
$153 nightly
$174 total
Sep 15 - Sep 16
Total with taxes and fees
8.4/10 Very Good! (3,751 reviews)
"Hotel and room were clean even for a busy event like the Bruno Mars concert. It is a great location for the North Shore events."
Reviewed on Aug 31, 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.
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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- University of Pittsburgh
- National Aviary
- Ppg Paints Arena
- Carnegie Science Center
- West End-Elliott Overlook Park
- Phipps Conservatory
- Where to stay in Pittsburgh
- Point State Park
- Carnegie Museum of Natural History
- Andy Warhol Bridge
- Carnegie Mellon University
- Carnegie Museum of Art
- Heinz Memorial Chapel
- Strip District Vacations
- Downtown Pittsburgh Vacations
- Kennywood
- Roberto Clemente Bridge
- Schenley Park
- David L Lawrence Convention Center
- Children's Museum of Pittsburgh
- Visit Downtown Pittsburgh
- Rachel Carson Bridge
- Cathedral of Learning
- Fort Pitt Block House
- Mount Washington Vacations
- North Shore Vacations
- Senator John Heinz Regional History Centre
- Andy Warhol Museum
- Pittsburgh Vacations
- Photo Antiquities Museum of Photographic History
- Lighthouse ArtSpace Pittsburgh
- Acrisure Stadium
- Duquesne Incline
- Market Square
- Grandview Overlook
- Byham Theater
- U.s. Steel Tower
- Monongahela Incline
- Pnc Park
- Visit Pittsburgh
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.