South Side Vacation Packages 2025/2026 from $369

South Side flight + hotel vacation packages

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

Hawthorn Extended Stay by Wyndham Saint Clairsville

$369

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Pittsburgh (PIT)

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the business center, express check-in, and conference space. There's a 24-hour gym on site, and laundry facilities and free newspapers are also offered.

Wyndham Grand Pittsburgh Downtown

Downtown Pittsburgh

$491

per person

Nov 15 - Nov 17

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) 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.

Hotel Indigo Pittsburgh East Liberty by IHG

East Liberty

$394

per person

Nov 1 - Nov 4

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) 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

$574

per person

Nov 15 - Nov 17

found 1 day ago

Roundtrip non-stop flight included

Los Angeles (LAX) 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.

Seven Springs Resort Properties

$462

per person

Oct 24 - Oct 27

found 16 hours ago

Roundtrip flight included

Orlando (MCO) to Pittsburgh (PIT)

A full-service spa and an outdoor pool are featured at this smoke-free aparthotel. Enjoy the indoor pool and perks like free self parking and free WiFi. Laundry facilities are provided for your convenience.

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 22 - Sep 23

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

$151 nightly

$172 total

Sep 28 - Sep 29

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

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

Sep 21 - Sep 22

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

Omni William Penn Hotel

530 William Penn Place, Pittsburgh, PA

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$182 total

Sep 29 - Sep 30

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

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

One Bigelow Square, Pittsburgh, PA

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$135 total

Sep 28 - Sep 29

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

The Landing Hotel at Rivers Casino

757 Casino Dr, Pittsburgh, PA

$149 nightly

$170 total

Sep 7 - Sep 8

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

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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 $369. 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.