South Side Vacation Packages 2026 from $416

South Side flight + hotel vacation packages

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

Wyndham Grand Pittsburgh Downtown

Downtown Pittsburgh

$416

per person

Apr 16 - Apr 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Pittsburgh (PIT)

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.

Placemakr Downtown Pittsburgh at The Pennsylvanian

Downtown Pittsburgh

Save 100% on your flight

$1,225

per person

Apr 22 - Apr 25

found 21 hours ago

Roundtrip non-stop flight included

Bismarck (BIS) 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.

Hilton Garden Inn Pittsburgh Airport

Save 100% on your flight

$772

per person

Apr 21 - Apr 25

found 1 day ago

Roundtrip non-stop flight included

Bismarck (BIS) 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.

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

Save 100% on your flight

$568

per person

May 15 - May 17

found 1 day ago

Roundtrip flight included

New York (NYC) 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.

Stay Pittsburgh

Downtown Pittsburgh

Save 100% on your flight

$1,406

per person

Apr 22 - Apr 25

found 1 day ago

Roundtrip non-stop flight included

Bismarck (BIS) 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.

Top South Side hotels deals

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

20 S 10th St Pittsburgh PA

Free Cancellation

$75 nightly

$86 total

Mar 16 - Mar 17

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

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl Pittsburgh PA

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$122 total

Mar 22 - Mar 23

Total with taxes and fees

Pool

Pet friendly

Omni William Penn Hotel

530 William Penn Place Pittsburgh PA

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$181 total

Mar 21 - Mar 22

Total with taxes and fees

This luxury 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

$102 nightly

$117 total

Mar 16 - Mar 17

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

Etage Executive Living

424 Stanwix St. Pittsburgh PA

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$144 total

Mar 10 - Mar 11

Total with taxes and fees

A rooftop terrace, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the business center and free internet in public areas.

Pet friendly

Free WiFi

Hilton Garden Inn Pittsburgh University Place

3454 Forbes Ave Pittsburgh PA

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$138 total

Mar 15 - Mar 16

Total with taxes and fees

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.

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.

PPG Paints Arena

4.5/5(596 reviews)

Catch an event at PPG Paints Arena during your trip to Pittsburgh. Experience the acclaimed theater scene or attend a sporting event in this vibrant area.

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.

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 $416. 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.