South Side Vacation Packages 2026 from $505

South Side flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Wyndham Grand Pittsburgh Downtown

Downtown Pittsburgh

Save 100% on your flight

$505

per person

May 14 - May 18

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. There's a gym on site, and a 24-hour front desk and express check-out are also provided.

Holiday Inn Express & Suites Pittsburgh North Shore by IHG

North Shore

Save 100% on your flight

$953

per person

May 14 - May 18

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Hotel Indigo Pittsburgh East Liberty by IHG

East Liberty

$532

per person

May 14 - May 18

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a computer station, and luggage storage are also on offer.

Pittsburgh Marriott City Center

Downtown Pittsburgh

$584

per person

May 14 - May 18

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Self parking, a grocery/convenience store, and a lobby fireplace are also offered.

Hotel Indigo Pittsburgh University-Oakland by IHG

Oakland

$645

per person

May 14 - May 18

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the a rooftop terrace and perks like a free area shuttle.

Top South Side hotels deals

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

20 S 10th St Pittsburgh PA

Free Cancellation

$80 nightly

$91 total

Mar 18 - Mar 19

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free buffet breakfast is served.

Pool

Breakfast included

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl Pittsburgh PA

Free Cancellation

Reserve now, pay when you stay

$124 nightly

$141 total

Apr 1 - Apr 2

Total with taxes and fees

Pool

Pet friendly

Omni William Penn Hotel

530 William Penn Place Pittsburgh PA

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$181 total

Mar 21 - Mar 22

Total with taxes and fees

This luxury hotel's 3 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.

Pet friendly

Free WiFi

Joinery Hotel Pittsburgh, Curio Collection by Hilton

453 Boulevard of the Allies Pittsburgh PA

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$122 total

Mar 29 - Mar 30

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and valet parking. A terrace, a snack bar/deli, and luggage storage are also on offer.

Pet friendly

Free WiFi

Etage Executive Living

424 Stanwix St. Pittsburgh PA

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$144 total

Mar 15 - Mar 16

Total with taxes and fees

A rooftop terrace, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the business center and free internet in public areas.

Pet friendly

Free WiFi

Hilton Garden Inn Pittsburgh University Place

3454 Forbes Ave Pittsburgh PA

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$145 total

Mar 22 - Mar 23

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A snack bar/deli, express check-out, and dry cleaning are also on offer.

Pet friendly

Free WiFi

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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.

Popular places to visit

PNC Park

Root for the Pittsburgh Pirates at this iconic stadium, which blends a timeless ballpark atmosphere with modern amenities.

PPG Paints Arena

Catch an event at PPG Paints Arena during your trip to Pittsburgh. Experience the acclaimed theater scene or attend a sporting event in this vibrant area.

University of Pittsburgh

Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

Frequently asked questions

How much are vacation packages to South Side?

Travelocity provides package deals to South Side, as well as flights and hotels, from an impressive $505. With the money you save, you could book some cool tours or possibly tack on a few extra nights to your exciting getaway.

Where can I get the best vacation package deals for South Side?

For a fun and affordable package deal to South Side, turn to Travelocity. Select from 400 airlines and 1,000,000 properties around the world to create the ideal adventure — you're spoiled for choice!

Why should I purchase my South Side vacation package via Travelocity?

Incredible savings, loads of inspiring destinations and 24/7 customer service — that's why. And with our Price Match Guarantee, you can rest easy knowing that you'll always get the best possible deal with Travelocity.

Can I save money on my South Side car rental if I combine it with hotels and flights?

Definitely — and if you also add an experience or activity to your South Side vacation package, you'll save some more. With a package from Travelocity, you can find things to do in the area that are just right for you. Then, jump in your rental car and work your way through the list. Geneva State Park is one must-see sight to visit. You'll find it 110 mi from South Side.

What is there to do in South Side?

Follow the lead of fellow travelers and head to Rex Theater. No visit to South Side would feel complete without a stop at this notable attraction.