South Side Vacation Packages 2025 from $242

South Side flight + hotel vacation packages

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

OYO Hotel North Lima OH - Boardman

per person

Apr 11 - Apr 16

found 1 day ago

Roundtrip non-stop flight included

Boise (BOI) to Pittsburgh (PIT)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Luggage storage and laundry facilities are also provided.

Hilton Garden Inn Pittsburgh University Place

Central Oakland

Save 100% on your flight

per person

Mar 28 - Apr 4

found 1 hour ago

Roundtrip non-stop flight included

Miami (MIA) to Pittsburgh (PIT)

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.

Hampton Inn & Suites Pittsburgh-Downtown

Downtown Pittsburgh

Save 100% on your flight

per person

Mar 28 - Apr 4

found 1 hour ago

Roundtrip non-stop flight included

Miami (MIA) to Pittsburgh (PIT)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

Stay Pittsburgh

Downtown Pittsburgh

Save 100% on your flight

per person

Mar 28 - Apr 4

found 1 hour ago

Roundtrip non-stop flight included

Miami (MIA) to Pittsburgh (PIT)

Free WiFi in public areas, express check-in, and express check-out are available at this aparthotel. Luggage storage, laundry facilities, and a virtual front desk are also on offer.

Residence Inn Cranberry Township Pittsburgh by Marriott

per person

Mar 28 - Apr 4

found 1 hour ago

Roundtrip non-stop flight included

Miami (MIA) to Pittsburgh (PIT)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free buffet breakfast each morning.

Top South Side hotels deals

Holiday Inn Express Hotel & Suites Pittsburgh-South Side, an IHG Hotel

20 S 10th St, Pittsburgh, PA

Free Cancellation

$104

includes taxes & fees

$91 per night

Mar 25 - Mar 26

This hotel features an indoor pool and a 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

$153

includes taxes & fees

$134 per night

Feb 26 - Feb 27

The hotel's indoor pool, gym, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A restaurant, a 24-hour front desk, and a coffee shop are also provided.

Pool

Pet friendly

Omni William Penn Hotel

530 William Penn Place, Pittsburgh, PA

Free Cancellation

Reserve now, pay when you stay

$181

includes taxes & fees

$159 per night

Mar 2 - Mar 3

This historic 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

$121

includes taxes & fees

$106 per night

Mar 27 - Mar 28

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

The Landing Hotel at Rivers Casino

757 Casino Dr, Pittsburgh, PA

$154

includes taxes & fees

$135 per night

Mar 17 - Mar 18

This smoke-free hotel features a casino and 5 restaurants. Traveling on business? Take advantage of the free WiFi in public areas and free valet parking. Relax with a drink at one of the 4 bars/lounges and enjoy free perks like continental breakfast and free self parking.

Breakfast included

Parking included

Kimpton Hotel Monaco Pittsburgh, an IHG Hotel

620 William Penn Place, Pittsburgh, PA

Free Cancellation

$198

includes taxes & fees

$174 per night

Mar 16 - Mar 17

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, laundry service, and valet parking. A lobby fireplace, a communal living room, and WiFi in public areas 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

4.5/5(780 reviews)

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

University of Pittsburgh

4.5/5(843 reviews)

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.

The Gates Hillman Center is a unique building that houses the computer science program and research. I love how outside the box the building is #StunningStructures

Carnegie Mellon University

4.5/5(520 reviews)

Walk around the campus of Carnegie Mellon University, 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 $242. 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.