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South Side Kid friendly Vacations

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Top Kid friendly vacation packages in South Side

Price found within the past 48 hours. Click for updated prices.
  • Free buffet breakfast
    Sep 12 - Sep 14

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

    South Side Flats
    2 nights
    2.5 star property
    7.8/10 - Good (1,004 reviews)
    "We stayed here because our daughter was in Magee with pregnancy complications and she was to be induced on a certain date so we came and stayed for a few days so we didn't have to drive an hour a way every day. We unfortunately had to check out sooner and rushed packing due to an emergency with our daughter which thankfully all was well with baby and mom, but we figured out a day later we left important items in one of the drawers. The staff was very helpful and was able to get our belongings..."
    Reviewed July 18, 2026
    Roundtrip • Atlanta (ATL) - Pittsburgh (PIT)
    ATL - PIT • 1 stop PIT - ATL • 1 stop
    $571
    $549
    per traveler
    found 1 day ago
    Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG
  • Living area
    Sep 3 - Sep 6

    Traveler's Rest Hotel + Flight

    South Side Flats
    3 nights
    2.0 star property
    9.6/10 - Exceptional (109 reviews)
    "Really cool building. Although our private bathroom was across the hall, it was clean and no problems to use. Hosts were excellent. Great coffee! Would definitely stay again!"
    Reviewed July 16, 2026
    Roundtrip • Boston (BOS) - Pittsburgh (PIT)
    BOS - PIT • Nonstop PIT - BOS • Nonstop
    $855
    $710
    per traveler
    found 18 hours ago
    Traveler's Rest Hotel
  • Lobby
    Sep 26 - Oct 1

    SpringHill Suites by Marriott Pittsburgh Southside Works + Flight

    South Side Flats
    5 nights
    3.0 star property
    8.6/10 - Excellent (1,004 reviews)
    Roundtrip • New York (JFK) - Pittsburgh (PIT)
    JFK - PIT • Nonstop PIT - JFK • Nonstop
    $794
    $681
    per traveler
    found 1 day ago
    SpringHill Suites by Marriott Pittsburgh Southside Works
  • Terrace/patio
    Oct 6 - Oct 11

    HYATT house Pittsburgh-South Side + Flight

    South Side Flats
    5 nights
    3.0 star property
    8.6/10 - Excellent (1,001 reviews)
    "Loved the view of the river from my room snd the outdoor patio!"
    Reviewed July 17, 2026
    Roundtrip • Atlanta (ATL) - Pittsburgh (PIT)
    ATL - PIT • Nonstop PIT - ATL • Nonstop
    $1,171
    $1,111
    per traveler
    found 10 hours ago
    HYATT house Pittsburgh-South Side

Top Kid friendly South Side Hotels

Free buffet breakfast

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
7.8 out of 10, Good, (1,004 reviews)
"We stayed here because our daughter was in Magee with pregnancy complications and she was to be induced on a certain date so we came and stayed for a few days so we didn't have to drive an hour a way every day. We unfortunately had to check out sooner and rushed packing due to an emergency with our daughter which thankfully all was well with baby and mom, but we figured out a day later we left important items in one of the drawers. The staff was very helpful and was able to get our belongings...
$79 nightly
The price is $90
Aug 3 - Aug 4
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

FAQs: family vacation packages in South Side

How can I find the best family vacation packages in South Side?

For fam-tastic vacation packages in South Side, check the family-friendly filter and add child-charming amenities, like water parks and pools. Read reviews written by other broods to be sure your chosen stay packs plenty of rest and play.

How can I book family-friendly vacations in South Side on a budget?

For family- and wallet-friendly trips, filter your search results by budget. You can also sort by price. When bringing the whole brigade on a budget, consider staying in low season or outside the city or. To save more coin, accommodation with a kitchen can be your friend—a bowl of pasta at home is always cheaper than feeding the team at a restaurant.

What does a family trip to South Side cost?

You could book your amazing family trip to South Side just $549. But with so many brilliant breaks on offer, there’s something for every wallet. Prices and availability are subject to change. Additional terms may apply.

Can I book an all-inclusive South Side family vacation package?

Check the all-inclusive filter for an all-you-could-ever-wish-for family vacay. Click more of your favorite filters for even more extravagance. Perhaps an ocean view, spa, or hot tub. Maybe a water park, epic kids club, or activities galore.

How can I plan a fun family vacation in South Side?

Search for stays with kid-satisfying extras, like water parks, and teenage-friendly free Wi-Fi, so they can post about all their vacation adventures for all their buddies back home. Book up local attractions, excursions, and experiences—and they might even put their phone down for a few minutes.

How can I find South Side family vacation deals?

Delightful deals often dwell outside high season, so move your travel dates around for top deals. You can also book up a little away from the major South Side landmarks to save cash. Whenever you wish to travel, sort your search results by deals for the most brilliant bargains.

Can I book a South Side family vacation package with free cancellation and/or flexible dates?

Free cancellation makes for a hassle-free family vacation. Filter by payment option to find fully flexible trips, including buy now, pay later options.

Why should I book my South Side family trip with Expedia?

You can easily find fun for all the family with the super-handy filters. It’s easy to build your dream kid-friendly vacation in just a few clicks. And you can bundle your accommodation, airfare, and car rental in just a few more.