South Side Vacation Packages 2025/2026 from $239

South Side flight + hotel vacation packages

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

Quality Inn Pittsburgh Airport

per person

Oct 10 - Oct 13

found 8 hours ago

Roundtrip flight included

New York (LGA) to Pittsburgh (PIT)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. Guests will appreciate freebies like buffet breakfast and free self parking.

Wyndham Grand Pittsburgh Downtown

Downtown Pittsburgh

Save 100% on your flight

per person

Oct 10 - Oct 13

found 8 hours ago

Roundtrip flight included

New York (LGA) to Pittsburgh (PIT)

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.

Americas Best Value Inn Pittsburgh Airport

per person

Aug 30 - Sep 3

found 14 hours ago

Roundtrip flight included

Los Angeles (LAX) to Pittsburgh (PIT)

This motel doesn't skimp on freebies - guests receive free continental breakfast, free self parking, and a free airport shuttle. Traveling on business? Take advantage of the business center and free WiFi in public areas. A picnic area, a computer station, and dry cleaning are also on offer.

Placemakr Downtown Pittsburgh

Downtown Pittsburgh

Save 100% on your flight

per person

Oct 10 - Oct 13

found 8 hours ago

Roundtrip flight included

New York (LGA) to Pittsburgh (PIT)

A 24-hour gym, valet parking, and laundry facilities are featured at this apartment. WiFi in public areas is free. A hair salon, dry cleaning, and luggage storage are also on offer.

461 Melwood Suites Unit 101 2Bed/2Bath

Oakland

per person

Oct 10 - Oct 13

found 12 hours ago

Roundtrip non-stop flight included

San Antonio (SAT) to Pittsburgh (PIT)

Top South Side hotels deals

SpringHill Suites by Marriott Pittsburgh Southside Works

2950 S Water St, Pittsburgh, PA

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$102 total

Jul 27 - Jul 28

Total includes taxes and fees

This hotel doesn't skimp on freebies - guests receive free breakfast and free WiFi. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's a gym on site, and a 24-hour front desk and a snack bar/deli are also provided.

Breakfast included

Free WiFi

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl, Pittsburgh, PA

Free Cancellation

Reserve now, pay when you stay

$125 nightly

$142 total

Jul 16 - Jul 17

Total includes 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

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$163 total

Jul 28 - Jul 29

Total includes 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

$127 nightly

$144 total

Jul 20 - Jul 21

Total includes 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

Drury Plaza Hotel Pittsburgh Downtown

745 Grant Street, Pittsburgh, PA

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$136 total

Jul 20 - Jul 21

Total includes 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. Enjoy the 24-hour gym and free buffet breakfast each morning.

Pool

Hot Tub

Holiday Inn Express & Suites Pittsburgh North Shore by IHG

228 Federal St, Pittsburgh, PA

Free Cancellation

$111 nightly

$127 total

Jul 27 - Jul 28

Total includes 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. Enjoy the free buffet breakfast each morning.

Pool

Breakfast 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 acclaimed theater scene 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 $239. 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.