South Side Vacations 2025/2026 from CA $657

South Side flight + hotel packages

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

Wingate by Wyndham Cranberry

per person

Aug 31 - Sep 5

found 1 day ago

Roundtrip non-stop flight included

Winnipeg (YWG) to Pittsburgh (PIT)

Book a stay at this business-friendly hotel in Cranberry Township. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions UPMC Lemieux Sports Complex and Fun Fore All are located nearby.

Cedar Grove Motel

per person

Sep 27 - Sep 28

found 1 day ago

Roundtrip flight included

Winnipeg (YWG) to Pittsburgh (PIT)

Stay at this motel in Altoona. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Railroaders Memorial Museum and Quaint Corner Children's Discovery Center are located nearby.

Top South Side hotels deals

SpringHill Suites by Marriott Pittsburgh Southside Works

2950 S Water St, Pittsburgh, PA

Free cancellation

Reserve now, pay when you stay

CA $142

CA $162 total

Aug 10 - Aug 11

includes taxes & fees

Stay at this 3-star business-friendly hotel in Pittsburgh. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.

Breakfast included

Free WiFi

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl, Pittsburgh, PA

Free cancellation

Reserve now, pay when you stay

CA $164

CA $187 total

Jul 27 - Jul 28

includes taxes & fees

Stay at this 3.5-star business-friendly hotel in Pittsburgh. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PNC Park and Acrisure Stadium are located nearby.

Pool

Pet-friendly

Omni William Penn Hotel

530 William Penn Place, Pittsburgh, PA

Free cancellation

Reserve now, pay when you stay

CA $197

CA $224 total

Aug 3 - Aug 4

includes taxes & fees

Book a stay at this historic hotel in Pittsburgh. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.

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

CA $174

CA $198 total

Jul 27 - Jul 28

includes taxes & fees

Stay at this 4-star business-friendly hotel in Pittsburgh. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.

Pet-friendly

Free WiFi

Drury Plaza Hotel Pittsburgh Downtown

745 Grant Street, Pittsburgh, PA

Free cancellation

Reserve now, pay when you stay

CA $163

CA $186 total

Jul 27 - Jul 28

includes taxes & fees

Stay at this 3-star business-friendly hotel in Pittsburgh. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.

Pool

Hot tub

Pittsburgh Marriott City Center

112 Washington Pl, Pittsburgh, PA

Free cancellation

Reserve now, pay when you stay

CA $162

CA $185 total

Aug 17 - Aug 18

includes taxes & fees

Stay at this 3.5-star business-friendly hotel in Pittsburgh. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions PPG Paints Arena and PNC Park are located nearby.

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(67 reviews)

Catch an event at PNC Park during your trip to Pittsburgh. Amble around this vibrant area's riverfront or experience its acclaimed theater scene.

University of Pittsburgh

4.5/5(36 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(94 reviews)

Catch an event at Acrisure Stadium during your trip to Pittsburgh. Stroll along the riverfront or attend a sporting event in the area.

South Side Vacations

You don't have to be full of local knowledge to have a great time in South Side, but you will need to have an idea about a few basic facts before you head off.

South Side is a neighborhood in the fantastic city of Pittsburgh. To get there, travel 2 miles (3 kilometers) to the southeast of the center.

Forget about the sights — it's the locals that make a place tick. Here in Pittsburgh, there are 310,000 of them.

Places to visit in South Side

The intimacy and accomplishment of theater is not to be missed. Buy your tickets for a play at Pittsburgh Playhouse and experience its magic and charm for yourself! Want some more options? Sure, singing along to tunes on your computer is nice, but it'll never compare with the thrill of seeing an invigorating live performance! So why not book front-row seats to an event at Rex Theater?

Where do you fly into for South Side?

All ready to kick-start your next fantastic adventure? Well, South Side is about 15 miles (24 kilometers) from Pittsburgh International Airport (PIT).

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 CA $657. 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 177 kilometers 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.