South Side Vacation Packages 2025/2026 from $359

South Side flight + hotel vacation packages

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

Hotel Indigo Pittsburgh East Liberty by IHG

East Liberty

Save 100% on your flight

$359

per person

Dec 27 - Jan 3

found 6 hours 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.

Fairmont Pittsburgh

Downtown Pittsburgh

Save 100% on your flight

$443

per person

Jan 8 - Jan 10

found 1 day ago

Roundtrip flight included

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

A full-service spa, 2 restaurants, and A 24-hour gym are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Relax with a drink at one of the 2 bars/lounges and enjoy the sauna.

Residence Inn Cranberry Township Pittsburgh by Marriott

Save 100% on your flight

$418

per person

Dec 27 - Jan 3

found 6 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

Homewood Suites by Hilton Pittsburgh Southpointe

Save 100% on your flight

$508

per person

Dec 27 - Jan 3

found 6 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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. Guests will appreciate freebies like buffet breakfast and free self parking.

DoubleTree by Hilton Washington Meadow Lands Casino Area

Save 100% on your flight

$521

per person

Dec 27 - Jan 3

found 6 hours ago

Roundtrip flight included

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

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 12 conference rooms, free WiFi in public areas, and laundry service. Enjoy the gym and perks like free self parking.

Top South Side hotels deals

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

20 S 10th St, Pittsburgh, PA

$83 nightly

$95 total

Nov 23 - Nov 24

Total with taxes and fees

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

$104 nightly

$119 total

Dec 4 - Dec 5

Total with taxes and fees

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

$167 nightly

$191 total

Nov 16 - Nov 17

Total with taxes and fees

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

$116 nightly

$133 total

Nov 20 - Nov 21

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

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

One Bigelow Square, Pittsburgh, PA

$103 nightly

$118 total

Nov 24 - Nov 25

Total with taxes and fees

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

Pool

Pet friendly

DoubleTree by Hilton Pittsburgh - Green Tree

500 Mansfield Avenue, Pittsburgh, PA

$94 nightly

$108 total

Nov 23 - Nov 24

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking, a 24-hour business center, and a coffee shop are also offered.

Pet friendly

Parking included

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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 fascinating museums in this vibrant area.

Heinz Field which includes a lake or waterhole

Acrisure Stadium

4.5/5(998 reviews)

Catch an event at Acrisure Stadium during your trip to Pittsburgh. Stroll along the riverfront or attend a sporting event in the 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 $359. 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.