South Side Vacation Packages 2025 from $456

South Side flight + hotel vacation packages

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

Stay Pittsburgh

Downtown Pittsburgh

per person

May 9 - May 11

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Omni William Penn Hotel

Downtown Pittsburgh

per person

May 9 - May 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Pittsburgh (PIT)

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.

The Westin Pittsburgh, a Marriott Hotel

Downtown Pittsburgh

per person

May 17 - May 19

found 15 hours ago

Roundtrip non-stop 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.

Homewood Suites by Hilton Pittsburgh Downtown

Downtown Pittsburgh

per person

Jun 19 - Jun 23

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Pittsburgh (PIT)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy the free on-the-go breakfast each morning.

Slopeside Hotel by Seven Springs Resort

per person

Jun 17 - Jun 19

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Pittsburgh (PIT)

This smoke-free aparthotel features ski-in/ski-out access, a full-service spa, and 4 restaurants. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy downhill skiing. Enjoy a meal in one of the 4 coffee shops/cafes and free perks like valet parking and WiFi in public areas.

Top South Side hotels deals

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

20 S 10th St, Pittsburgh, PA

Free Cancellation

$104

includes taxes & fees

$91 per night

Apr 20 - Apr 21

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

$149

includes taxes & fees

$131 per night

Apr 14 - Apr 15

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and free buffet breakfast each morning.

Pool

Breakfast included

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl, Pittsburgh, PA

Free Cancellation

Reserve now, pay when you stay

$199

includes taxes & fees

$175 per night

Apr 6 - Apr 7

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

Drury Plaza Hotel Pittsburgh Downtown

745 Grant Street, Pittsburgh, PA

Free Cancellation

Reserve now, pay when you stay

$116

includes taxes & fees

$102 per night

Apr 20 - Apr 21

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

Hampton Inn Pittsburgh University/Medical Center

3315 Hamlet Street, Pittsburgh, PA

Free Cancellation

Reserve now, pay when you stay

$106

includes taxes & fees

$93 per night

Apr 20 - Apr 21

This hotel doesn't skimp on freebies - guests receive free continental breakfast and free WiFi. Business travelers can take advantage of the 24-hour business center. Enjoy the gym and conveniences like a 24-hour front desk and concierge services.

Breakfast included

Pet friendly

Courtyard by Marriott Pittsburgh University Center

100 Lytton Avenue, Pittsburgh, PA

Free Cancellation

Reserve now, pay when you stay

$148

includes taxes & fees

$130 per night

Apr 20 - Apr 21

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi. Self parking, express check-out, and dry cleaning are also offered.

Pool

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 $456. 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.