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

South Side Adults Only Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
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    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

Top Adults Only vacation packages in South Side

Price found within the past 48 hours. Click for updated prices.
  • Dec 18 - Dec 21

    Hilton Garden Inn Pittsburgh Airport + Flight

    Coraopolis
    3 nights
    3.0 star property
    9.0/10 - Wonderful (1,004 reviews)
    Roundtrip • Vancouver (YVR) - Pittsburgh (PIT)
    YVR - PIT • 1 stop PIT - YVR • 1 stop
    CA $1,256
    CA $1,127
    per traveller
    found 22 hours ago
    Hilton Garden Inn Pittsburgh Airport
  • Dec 21 - Dec 27

    My Place Hotel - Pittsburgh North/Monaca, PA + Flight

    Monaca
    6 nights
    2.5 star property
    8.2/10 - Very good (447 reviews)
    "Clean room"
    Reviewed October 29, 2026
    Roundtrip • Toronto (YYZ) - Pittsburgh (PIT)
    YYZ - PIT • Nonstop PIT - YYZ • Nonstop
    CA $1,298
    CA $1,129
    per traveller
    found 1 day ago
    My Place Hotel - Pittsburgh North/Monaca, PA
  • Dec 21 - Dec 27

    Pittsburgh Marriott North + Flight

    Cranberry Township
    6 nights
    3.5 star property
    9.0/10 - Wonderful (854 reviews)
    Roundtrip • Toronto (YYZ) - Pittsburgh (PIT)
    YYZ - PIT • Nonstop PIT - YYZ • Nonstop
    CA $1,549
    CA $1,375
    per traveller
    found 1 day ago
    Pittsburgh Marriott North
  • Dec 21 - Dec 27

    Courtyard by Marriott Pittsburgh North/Cranberry Woods + Flight

    Cranberry Township
    6 nights
    3.0 star property
    9.0/10 - Wonderful (800 reviews)
    "All good"
    Reviewed November 8, 2026
    Roundtrip • Toronto (YYZ) - Pittsburgh (PIT)
    YYZ - PIT • Nonstop PIT - YYZ • Nonstop
    CA $1,403
    CA $1,263
    per traveller
    found 1 day ago
    Courtyard by Marriott Pittsburgh North/Cranberry Woods
  • Dec 21 - Dec 27

    Candlewood Suites Pittsburgh Cranberry by IHG + Flight

    Cranberry Township
    6 nights
    2.5 star property
    9.0/10 - Wonderful (710 reviews)
    "Room was clean but smells like bootie hole!"
    Reviewed August 16, 2026
    Roundtrip • Toronto (YYZ) - Pittsburgh (PIT)
    YYZ - PIT • Nonstop PIT - YYZ • Nonstop
    CA $1,448
    CA $1,334
    per traveller
    found 1 day ago
    Candlewood Suites Pittsburgh Cranberry by IHG

Discover the most popular places to visit in South Side

What to do in South Side

Top Adults Only South Side Hotels

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.

Frequently Asked Questions

How much does a South Side vacation package cost?

Much less than you might think — from only CA $1,127, actually! By combining hotels, flights and car rentals into a customized package, your getaway to South Side is just clicks away.

How do I get a cheap travel package to South Side?

Search for flights that suit your busy schedule, add a hotel to your booking and watch the savings grow with a South Side vacation package. It's as easy as that! From hotels and flights to rental cars and tours, Expedia is where your cheap getaway begins. And with more than 550 airlines and 1,000,000 properties around the world to select from, you won't be short of choice.

Where should I stay in South Side?

Travelers come from all over the world to experience Acrisure Stadium and PNC Park in South Side. Book a room near these must-see attractions to make sightseeing a breeze.

What are the top hotels in South Side?

If it's your first visit to South Side, lock in a room at Kasa South Side Pittsburgh or SpringHill Suites by Marriott Pittsburgh Southside Works. Both hotels offer friendly service and are favorites with lots of travelers.

How far in advance should I book my South Side vacation?

Reward yourself with the widest variety at the cheapest prices by booking your South Side vacation early. Airlines generally publish flight tickets around a year before departure, so reserve your spot as soon as you can. That said, Expedia is committed to providing you with the best bargains around, so it's never a bad time to book your dream vacation!

What does an Expedia South Side travel package include?

Flights, hotels and a shiny set of wheels for all your road trip adventures. Simply select your favorite bundle and get access to incredible deals. Once you've made your booking, add on a few tours and activities and watch your savings stack up. When it comes to crafting your South Side break, you're in charge!

What should I know before booking a South Side travel package?

You'll score impressive savings when you bundle your hotels, flights and rental cars into a package. Not only that, booking everything together just makes things easier. So why waste your time or money? Whether you're organizing a ritzy romantic getaway or a low-cost family road trip, explore our package deals today.

Can I choose my airline with a South Side Expedia vacation package?

With a vacation package, the choice is in your hands. Whether you want to fly to South Side in business or coach, simply pick from the available airline options. Expedia has access to over 550 partner airlines around the world.

If I'm not able to travel, can I cancel my South Side vacation package?

Your situation can change without warning, so yes, you can. You may be able to cancel or amend your South Side vacation package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, airline or hotel may charge a fee. Need more information? Look up our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.