South Side Vacation Packages 2025/2026 from $242

South Side flight + hotel vacation packages

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

Hilton Garden Inn Pittsburgh Airport

$242

per person

Oct 24 - Oct 26

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Pittsburgh (PIT)

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 free airport shuttle. Enjoy the 24-hour gym and perks like free self parking.

Hotel Indigo Pittsburgh East Liberty by IHG

East Liberty

Save 100% on your flight

$360

per person

Sep 19 - Sep 22

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

Save 100% on your flight

$557

per person

Sep 19 - Sep 22

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Wyndham Grand Pittsburgh Downtown

Downtown Pittsburgh

Save 100% on your flight

$352

per person

Sep 19 - Sep 22

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Joinery Hotel Pittsburgh, Curio Collection by Hilton

Downtown Pittsburgh

Save 100% on your flight

$466

per person

Oct 24 - Oct 26

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Pittsburgh (PIT)

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.

Top South Side hotels deals

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

20 S 10th St, Pittsburgh, PA

Free Cancellation

$79 nightly

$90 total

Sep 8 - Sep 9

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. Free buffet breakfast is served.

Pool

Breakfast included

HYATT house Pittsburgh-South Side

2795 S Water St, Pittsburgh, PA

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$163 total

Aug 31 - Sep 1

Total includes taxes and fees

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 free buffet breakfast each morning.

Breakfast included

Pet friendly

SpringHill Suites by Marriott Pittsburgh Southside Works

2950 S Water St, Pittsburgh, PA

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$136 total

Aug 26 - Aug 27

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

$147 nightly

$167 total

Aug 20 - Aug 21

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

Joinery Hotel Pittsburgh, Curio Collection by Hilton

453 Boulevard of the Allies, Pittsburgh, PA

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$137 total

Aug 25 - Aug 26

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

Omni William Penn Hotel

530 William Penn Place, Pittsburgh, PA

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$163 total

Sep 2 - Sep 3

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

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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.

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.

Heinz Field which includes a lake or waterhole

Acrisure Stadium

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 $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.