South Side Vacation Packages 2026 from $337

South Side flight + hotel vacation packages

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

Hilton Garden Inn Pittsburgh University Place

Central Oakland

$337

per person

Jul 7 - Jul 9

found 1 day ago

Roundtrip flight included

New York (NYC) 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.

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

Save 100% on your flight

$667

per person

Jul 16 - Jul 19

found 1 day ago

Roundtrip flight included

New York (JFK) to Pittsburgh (PIT)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the steam room and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.

Hyatt Regency Pittsburgh International Airport

$445

per person

Jul 16 - Jul 19

found 1 day ago

Roundtrip flight included

New York (JFK) 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 free airport shuttle. Self parking, a coffee shop, and express check-in are also offered.

La Quinta Inn by Wyndham Pittsburgh Airport

$359

per person

Jul 16 - Jul 19

found 1 day ago

Roundtrip flight included

New York (JFK) to Pittsburgh (PIT)

This hotel 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 24-hour business center and free WiFi in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Melwood Suites Unit 107 Studio

Oakland

$1,082

per person

Aug 2 - Aug 9

found 24 hours ago

Roundtrip flight included

Houston (IAH) to Pittsburgh (PIT)

Top South Side hotels deals

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

20 S 10th St Pittsburgh PA

Free Cancellation

$83 nightly

$95 total

May 25 - May 26

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

SpringHill Suites by Marriott Pittsburgh Southside Works

2950 S Water St Pittsburgh PA

Free Cancellation

Reserve now, pay when you stay

$122 nightly

$139 total

May 25 - May 26

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free breakfast and free WiFi. Traveling on business? Take advantage of the express check-out 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

$165 nightly

$188 total

May 26 - May 27

Total with taxes and fees

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.

Pool

Pet friendly

The Landing Hotel at Rivers Casino

757 Casino Dr Pittsburgh PA

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$154 total

May 25 - May 26

Total with taxes and fees

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

Omni William Penn Hotel

530 William Penn Place Pittsburgh PA

Free Cancellation

Reserve now, pay when you stay

$204 nightly

$233 total

May 25 - May 26

Total with taxes and fees

This smoke-free 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. A coffee shop, limo/town car service, and a computer station are also on offer.

Pet friendly

Free WiFi

Hyatt Regency Pittsburgh International Airport

710 Aviation Avenue Pittsburgh PA

Free Cancellation

Reserve now, pay when you stay

$158 nightly

$180 total

Jun 13 - Jun 14

Total with taxes and fees

Free airport shuttle

Pet friendly

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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(790 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(856 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.

Acrisure Stadium

4.5/5(1,015 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 $337. 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.