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 - (1,001 reviews)
    Roundtrip • Boston (BOS) - Pittsburgh (PIT)
    BOS - PIT • 1 stop PIT - BOS • 1 stop
    $511
    $444
    per traveler
    found 1 day 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 1 day ago
    Stay Pittsburgh
  • A modern hotel lobby with a central seating area, large windows, and contemporary furnishings.
    Jan 8 - Jan 12

    Hyatt Regency Pittsburgh International Airport + Flight

    Pittsburgh
    4 nights
    3.5 star property
    9.0/10 - Wonderful (1,798 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 spacious indoor area with multiple tables and chairs, a bar area with televisions, and large windows offering a view of greenery outside.
    Dec 11 - Dec 13

    The Landing Hotel at Rivers Casino + Flight

    North Side
    2 nights
    2.0 star property
    9.4/10 - Exceptional (2,532 reviews)
    Roundtrip • Boston (BOS) - Pittsburgh (PIT)
    BOS - PIT • 1 stop PIT - BOS • 1 stop
    $679
    $586
    per traveler
    found 1 day 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 (1,367 reviews)
    "No complaints my stay was great service at a reasonable rate"
    Reviewed November 6, 2026
    Roundtrip • Boston (BOS) - Pittsburgh (PIT)
    BOS - PIT • 1 stop PIT - BOS • 1 stop
    $676
    $584
    per traveler
    found 1 day 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

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.