South Side Vacations from $349

Book a Hotel + Flight or Car together to unlock savings

Your South Side Vacation

Well known for its walking and culture, South Side draws visitors from near and far. Let our South Side vacation packages give you a peek into this neighborhood and everything it has to offer. Eager to head out and see the sights during your trip to South Side? Be sure to stop by nearby attractions like Acrisure Stadium, University of Pittsburgh and PNC Park. Don't just dream it — do it! Book your ideal South Side vacation with Expedia and get to where you're going your way.

The Latest South Side vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Pittsburgh East Liberty by IHG
The Westin Pittsburgh, a Marriott Hotel
Wyndham Grand Pittsburgh Downtown
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Kimpton Hotel Monaco Pittsburgh by IHG
Don't see what you're looking for?
See all available trips from Columbus to South Side
View all trips

Discover the most popular places to visit in South Side

What to do in South Side

South Side Hotel Deals

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

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

2.5 out of 5
20 S 10th St, Pittsburgh, PA
Fully refundable
$83 nightly
The price is $95 total per night from Sep 8 to Sep 9
$95 total
Sep 8 - Sep 9
Total includes taxes and fees
7/10 Good! (1,008 reviews)
"Bed was very comfortable. Parking lot gate left wide open, so not secure."

Reviewed on Aug 9, 2025

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG
SpringHill Suites by Marriott Pittsburgh Southside Works

SpringHill Suites by Marriott Pittsburgh Southside Works

3 out of 5
2950 S Water St, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $118 total per night from Aug 24 to Aug 25
$118 total
Aug 24 - Aug 25
Total includes taxes and fees
8.4/10 Very Good! (968 reviews)
"Clean and well maitained room."

Reviewed on Aug 2, 2025

SpringHill Suites by Marriott Pittsburgh Southside Works
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
600 Commonwealth Pl, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $153 total per night from Aug 17 to Aug 18
$153 total
Aug 17 - Aug 18
Total includes taxes and fees
8/10 Very Good! (2,950 reviews)
"Great property to explore Downtown. Excellent view close to PNC Park. Great pool & hot tub with an amazing view. Courteous staff… speedy elavators!"

Reviewed on Aug 10, 2025

Wyndham Grand Pittsburgh Downtown
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.

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.