South Side Vacations

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Find the Best South Side Vacation Packages

South Side Hotel Deals

Holiday Inn Express Hotel & Suites Pittsburgh-South Side, an IHG Hotel
Holiday Inn Express Hotel & Suites Pittsburgh-South Side, an IHG Hotel
2.5 out of 5
20 S 10th St, Pittsburgh, PA
Fully refundable
The price is ₩133,383 per night from Feb 24 to Feb 25
₩133,383
₩152,056 total
includes taxes & fees
Feb 24 - Feb 25
7/10 Good! (1,001 reviews)
"The staff were amazing"

Reviewed on Feb 16, 2025

Holiday Inn Express Hotel & Suites Pittsburgh-South Side, an IHG Hotel
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
The price is ₩192,416 per night from Mar 2 to Mar 3
₩192,416
₩219,353 total
includes taxes & fees
Mar 2 - Mar 3
7.6/10 Good! (1,000 reviews)
"You’re definitely paying for location. Very easy walk to the football stadium, nice area. Smallest hotel room I’ve ever stayed in, but it did the job."

Reviewed on May 5, 2023

Wyndham Grand Pittsburgh Downtown
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Joinery Hotel Pittsburgh, Curio Collection by Hilton
4 out of 5
453 Boulevard of the Allies, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is ₩151,138 per night from Mar 23 to Mar 24
₩151,138
₩172,298 total
includes taxes & fees
Mar 23 - Mar 24
8.2/10 Very Good! (1,102 reviews)
"Property is very clean and well decorated. The staff was friendly and attentive"

Reviewed on Feb 17, 2025

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 1,720 properties in South Side
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.

Frequently asked questions

How much does a South Side vacation package cost?
Much less than you might think — from only , actually! By combining hotels, flights and car rentals into a customized package, your getaway to South Side is just clicks away.
How do I get a cheap travel package to South Side?
Search for flights that suit your busy schedule, add a hotel to your booking and watch the savings grow with a South Side vacation package. It’s as easy as that! From hotels and flights to rental cars and tours, Expedia is where your cheap getaway begins. And with more than 550 airlines and 1,000,000 properties around the world to select from, you won’t be short of choice.
Where should I stay in South Side?
Travelers come from all over the world to experience Acrisure Stadium and PNC Park in South Side. Book a room near these must-see attractions to make sightseeing a breeze.
What are the top hotels in South Side?
If it’s your first visit to South Side, lock in a room at Kasa South Side Pittsburgh or SpringHill Suites by Marriott Pittsburgh Southside Works. Both hotels offer friendly service and are favorites with lots of travelers.
How far in advance should I book my South Side vacation?
Reward yourself with the widest variety at the cheapest prices by booking your South Side vacation early. Airlines generally publish flight tickets around a year before departure, so reserve your spot as soon as you can. That said, Expedia is committed to providing you with the best bargains around, so it’s never a bad time to book your dream vacation!
What does an Expedia South Side travel package include?
Flights, hotels and a shiny set of wheels for all your road trip adventures. Simply select your favorite bundle and get access to incredible deals. Once you’ve made your booking, add on a few tours and activities and watch your savings stack up. When it comes to crafting your South Side break, you’re in charge!
What should I know before booking a South Side travel package?
You’ll score impressive savings when you bundle your hotels, flights and rental cars into a package. Not only that, booking everything together just makes things easier. So why waste your time or money? Whether you’re organizing a ritzy romantic getaway or a low-cost family road trip, explore our package deals today.
Can I choose my airline with a South Side Expedia vacation package?
With a vacation package, the choice is in your hands. Whether you want to fly to South Side in business or coach, simply pick from the available airline options. Expedia has access to over 550 partner airlines around the world.
If I'm not able to travel, can I cancel my South Side vacation package?
Your situation can change without warning, so yes, you can. You may be able to cancel or amend your South Side vacation package at no cost if you’ve booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, airline or hotel may charge a fee. Need more information? Look up our Customer Service Portal. We’re here to help make sure your trip goes off without a hitch.

Discover the most popular places to visit in South Side

Oakland featuring a garden

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.

University of Pittsburgh
Heinz Field which includes a lake or waterhole

Acrisure Stadium

4.5/5(998 reviews)

Giant ketchup bottles tilt onto the scoreboard to celebrate touchdowns in this innovative riverside football arena at the heart of Pittsburgh sports.

Acrisure Stadium
Kennywood showing rides

Kennywood

4.5/5(159 reviews)

Spend a fun-filled day making your way between over 30 rides and attractions in one of the oldest continually running amusement parks in the United States.

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