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

South Side Vacations from $444

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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 11 - Dec 13

    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 • Boston (BOS) - Pittsburgh (PIT)
    BOS - PIT • 1 stop PIT - BOS • 1 stop
    $511
    $444
    per traveler
    found 13 hours ago
    Americas Best Value Inn Pittsburgh Airport
  • A brick building with a large arched entrance labeled "STAYPGH".
    Dec 11 - Dec 13

    Stay Pittsburgh + Flight

    Downtown Pittsburgh
    2 nights
    2.0 star property
    8.0/10 - Very good (345 reviews)
    Roundtrip • Boston (BOS) - Pittsburgh (PIT)
    BOS - PIT • 1 stop PIT - BOS • 1 stop
    $602
    $502
    per traveler
    found 13 hours ago
    Stay Pittsburgh
  • A modern lobby with a reception desk, seating area, and a staircase leading to upper floors.
    Jan 8 - Jan 12

    Hyatt Regency Pittsburgh International Airport + Flight

    Pittsburgh
    4 nights
    3.5 star property
    9.0/10 - Wonderful (1,797 reviews)
    Roundtrip • Phoenix (PHX) - Pittsburgh (PIT)
    PHX - PIT • Nonstop PIT - PHX • Nonstop
    $746
    $629
    per traveler
    found 1 day ago
    Hyatt Regency Pittsburgh International Airport
  • A modern living room with a large window offering a scenic view of a lake and hills. There is a sofa set and a small coffee table with a remote control on it.
    Dec 11 - Dec 13

    The Landing Hotel at Rivers Casino + Flight

    North Side
    2 nights
    2.0 star property
    9.4/10 - Exceptional (2,528 reviews)
    "Everything was great."
    Reviewed November 6, 2026
    Roundtrip • Boston (BOS) - Pittsburgh (PIT)
    BOS - PIT • 1 stop PIT - BOS • 1 stop
    $679
    $586
    per traveler
    found 13 hours ago
    The Landing Hotel at Rivers Casino
  • A multi-story hotel with a brick facade, large windows, and a flagpole with an American flag.
    Dec 11 - Dec 13

    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 • Boston (BOS) - Pittsburgh (PIT)
    BOS - PIT • 1 stop PIT - BOS • 1 stop
    $676
    $584
    per traveler
    found 13 hours ago
    Hampton Inn & Suites Pittsburgh-Downtown

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

An indoor swimming pool with clear glass walls, a blue chair, and a small round table in the center.

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.