South Side Vacations from $403
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.
Wyndham Grand Pittsburgh Downtown
Downtown Pittsburgh
$403
per person
Sep 18 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8.2/10 Very Good! (3,705 reviews)
Minor issue at checkin, but they corrected it quickly and offered a free breakfast. Good service. Great location for baseball park and city attractions.
Reviewed on Aug 15, 2026
Stay Pittsburgh
Downtown Pittsburgh
$538
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
8/10 Very Good! (314 reviews)
Some confusion on my end with paying the deposit, as I thought I was paying for my room a second time, but the host was quick to clear it up. Another pleasant stay at this clean and quiet property.
Reviewed on Aug 9, 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: Museum of Illusions Entrance Ticket
$29
per adult
90% of travellers recommend
Black & Gold Pittsburgh History Tour for Sports Fans
$33
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
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
Aug 31 - Sep 1
Total with taxes and fees
8/10 Very Good! (1,017 reviews)
"Great place to stay when catching a game or concert. good walk or a cheap uber ride."
Reviewed on Aug 14, 2026
SpringHill Suites by Marriott Pittsburgh Southside Works
2950 S Water St Pittsburgh PA
Fully refundableReserve now, pay when you stay
$101 nightly
$115 total
Aug 23 - Aug 24
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Bad location.And didn't have the pool"
Reviewed on Aug 15, 2026
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
$124 nightly
$141 total
Aug 30 - Aug 31
Total with taxes and fees
8.4/10 Very Good! (3,693 reviews)
"Minor issue at checkin, but they corrected it quickly and offered a free breakfast. Good service. Great location for baseball park and city attractions."
Reviewed on Aug 15, 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.