South Side Vacation Packages 2026 from $680

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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.

The Landing Hotel at Rivers Casino

North Side

$680

per person

Dec 16 - Dec 19

found 2 hours ago

Roundtrip non-stop flight included

Burbank (BUR) to Pittsburgh (PIT)

9.4/10 Exceptional! (2,351 reviews)

Stay Pittsburgh

Downtown Pittsburgh

$933

per person

Nov 25 - Nov 29

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Pittsburgh (PIT)

8/10 Very Good! (332 reviews)

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

$1,047

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Pittsburgh (PIT)

8.6/10 Excellent! (1,000 reviews)

Oakmont Inn

Plum

$1,039

per person

Dec 17 - Dec 21

found 24 hours ago

Roundtrip non-stop flight included

Ontario Intl. Airport (ONT) to Pittsburgh (PIT)

10/10 Exceptional! (38 reviews)

Very quiet and incredibly clean! We absolutely loved the place!

Reviewed on Sep 27, 2026

The Inn on Negley

Shadyside

$919

per person

Dec 18 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Ontario Intl. Airport (ONT) to Pittsburgh (PIT)

10/10 Exceptional! (225 reviews)

This Inn is beautiful, perfectly located within a couple minutes of downtown, very well maintained, breakfast was wonderful, the room was super comfortable with quality linens and a very comfortable batch. Wonderful staff as well, Peter gave us some history of Pittsburgh and some ideas to make our trip back home even better! We plan on coming back to Pittsburgh and staying here again.

Reviewed on Sep 30, 2026

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Stay near popular South Side attractions

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.

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What to do in South Side

Pittsburgh: Museum of Illusions Entrance Ticket

$29

per adult

86% of travellers recommend

This tour is the best tour for sports fans! Big fun guaranteed!

Black & Gold Pittsburgh History Tour for Sports Fans

$33

per adult

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

$13

per adult

See all activities in South Side

South Side Hotel Deals

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

20 S 10th St Pittsburgh PA

Fully refundable

$83 nightly

$95 total

Nov 2 - Nov 3

Total with taxes and fees

8/10 Very Good! (1,023 reviews)

"My daughter and I were in town for the Olivia Rodrigo concert and arrived a bit early and we were told our room would be ready by 3. The front desk staff was going through a shift change but they were very attentive and pleasant. Our room was clean, modern and very nice. Shower was large and clean. ..."

Reviewed on Oct 1, 2026

SpringHill Suites by Marriott Pittsburgh Southside Works

2950 S Water St Pittsburgh PA

$105 nightly

$119 total

Nov 2 - Nov 3

Total with taxes and fees

8.6/10 Excellent! (1,003 reviews)

"Very nice room. Clean and well kept. Breakfast was delicious and the kitchen staff was so helpful. Trains passing all night long were annoying but that’s not the hotels issue. I’d stay there again"

Reviewed on Oct 2, 2026

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl Pittsburgh PA

Fully refundableReserve now, pay when you stay

$124 nightly

$141 total

Oct 22 - Oct 23

Total with taxes and fees

8.4/10 Very Good! (3,821 reviews)

"Todo estaba bien… la atención y el check-in fue rápido, me encantó la vista que tenia nuestras habitación, nos hospedamos una noche y estuvo bien."

Reviewed on Oct 2, 2026

See all 2,018 properties in South Side

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.