A park with autumn trees, a bridge, and a building labeled UPMC in the background.

South Side Vacations from $235

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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 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.
  • A reception area with a tiled floor, two patterned armchairs, a desk with a reception sign, and a large mirror.
    Dec 19 - Dec 21

    Americas Best Value Inn Pittsburgh Airport + Flight

    Coraopolis
    2 nights
    2.0 star property
    6.6/10 - (1,000 reviews)
    "Thanks."
    Reviewed November 3, 2026
    Roundtrip • Atlanta (ATL) - Pittsburgh (PIT)
    ATL - PIT • Nonstop PIT - ATL • 1 stop
    $296
    $235
    per traveler
    found 1 day ago
    Americas Best Value Inn Pittsburgh Airport
  • A rooftop lounge with seating and a view of the cityscape at dusk.
    Dec 19 - Dec 21

    Joinery Hotel Pittsburgh, Curio Collection by Hilton + Flight

    Downtown Pittsburgh
    2 nights
    4.0 star property
    8.4/10 - Very good (1,706 reviews)
    Roundtrip • Atlanta (ATL) - Pittsburgh (PIT)
    ATL - PIT • Nonstop PIT - ATL • 1 stop
    $558
    $405
    per traveler
    found 1 day ago
    Joinery Hotel Pittsburgh, Curio Collection by Hilton
  • A multi-story hotel with a brick facade, large windows, and a flagpole with an American flag.
    Dec 19 - Dec 21

    Hampton Inn & Suites Pittsburgh-Downtown + Flight

    Downtown Pittsburgh
    2 nights
    2.5 star property
    9.4/10 - Exceptional (1,366 reviews)
    "The property was clean and updated in a great location. The price was great compared to other properties in the area and included free parking and breakfast. The front desk staff was so friendly! We had one small issue with housekeeping and the manager more than made up for it. I’d definitely stay here again"
    Reviewed November 3, 2026
    Roundtrip • Atlanta (ATL) - Pittsburgh (PIT)
    ATL - PIT • Nonstop PIT - ATL • 1 stop
    $614
    $477
    per traveler
    found 1 day ago
    Hampton Inn & Suites Pittsburgh-Downtown
  • A spacious living room with a wooden ceiling, large windows with curtains, a leather sofa, a dining table, and a kitchen area.
    Dec 19 - Dec 21

    Traveler's Rest Hotel + Flight

    South Side Flats
    2 nights
    2.0 star property
    9.6/10 - Exceptional (131 reviews)
    "Room was clean, quiet. Owner very friendly."
    Reviewed November 3, 2026
    Roundtrip • Atlanta (ATL) - Pittsburgh (PIT)
    ATL - PIT • Nonstop PIT - ATL • 1 stop
    $599
    $477
    per traveler
    found 1 day ago
    Traveler's Rest Hotel
  • A cityscape with high-rise buildings, including a prominent Westin hotel.
    Dec 19 - Dec 21

    The Westin Pittsburgh, a Marriott Hotel + Flight

    Downtown Pittsburgh
    2 nights
    4.0 star property
    8.6/10 - Excellent (1,001 reviews)
    Roundtrip • Atlanta (ATL) - Pittsburgh (PIT)
    ATL - PIT • Nonstop PIT - ATL • 1 stop
    $650
    $518
    per traveler
    found 1 day ago
    The Westin Pittsburgh, a Marriott Hotel

Discover the most popular places to visit in South Side

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.
See properties

South Side Hotel Deals

A breakfast bar with various food items and a sign that says "Egg-Xactly The Start You Need".

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG
2.5 star property
South Side Flats, 0.7 mi from South Side
8.2 out of 10, Very good, (1,042 reviews)
"I will continue to stay here when I need a place on the southside. Check in is easy and smooth. Rooms are always nice and well stocked. I wish the breakfast was a lil better but that’s the only thing I can think of that needs an upgrade."
$95 nightly
The price is $108
Dec 7 - Dec 8
Total with taxes and fees
Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG
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.
See all properties in South Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.