South Side Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Top South Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Priory Hotel
North Side
CA $1,354
per person
Nov 26 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Pittsburgh (PIT)
9.6/10 Exceptional! (1,000 reviews)
A beautifully restored building. Convenient free parking. We were in town for a baseball game. They offered a free shuttle to and from the stadium. The room was clean and comfortable. Bath towels were thick. Bathrobes available. Complimentary breakfast was personalized. We ordered our breakfast the evening before and it was ready at the time we chose. The price was less than the corporate hotels close to the ballpark. The staff was courteous and helpful. This is a hidden gem. We will definitely stay here again.
Reviewed on Sep 23, 2026
Ready to book your vacation to South Side?
South Side Hotel Deals
Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG
20 S 10th St Pittsburgh PA
Fully refundable
CA $128
CA $146 total
Oct 22 - Oct 23
includes taxes & fees
8/10 Very good! (1,014 reviews)
"We had a very enjoyable stay! Everyone was polite, professional. Special thanks to Ebony who went out of her way to assist us when needed and went above and beyond to make sure we had a great experience at the hotel!"
Reviewed on Sep 21, 2026
SpringHill Suites by Marriott Pittsburgh Southside Works
2950 S Water St Pittsburgh PA
CA $172
CA $196 total
Oct 12 - Oct 13
includes taxes & fees
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
CA $174
CA $198 total
Oct 12 - Oct 13
includes taxes & fees
8.4/10 Very good! (3,783 reviews)
"Great location! Food was delicious! Staff was wonderful and helpful!"
Reviewed on Sep 23, 2026
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.
Stay near popular South Side attractions
Rex Theater
6.0/10 (1 review)
You can get tickets for a performance at Rex Theater on your trip to Pittsburgh. Check out the shops and top-notch restaurants in this family-friendly area.
What to do in South Side
Pittsburgh Pirates Baseball Game at PNC Park
CA $65
per adult
100% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
CA $40
per adult
94% of travellers recommend
Whiskey Rebellion & Prohibition Tour
CA $68
per adult
100% of travellers recommend
Frequently asked questions
How much does a South Side vacation package cost?
Much less than you might think — from only CA $1,286, 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.
Explore a world of travel with Expedia
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- Flights from Ottawa (YOW) to Pittsburgh (PIT)
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- Roberto Clemente Bridge
- Ppg Paints Arena
- Kennywood
- Visit Strip District
- Market Square
- Mount Washington Vacations
- Pittsburgh Vacations
- Andy Warhol Museum
- Pnc Park
- Sri Venkateswara Temple
- Visit South Side Flats
- Visit Pittsburgh
- The Waterfront
- Visit Downtown Pittsburgh
- Carnegie Museum of Natural History
- Rivers Casino
- National Aviary
- Heinz Hall
- Carnegie Mellon University
- Carnegie Science Center
- Phipps Conservatory
- Visit North Shore
- Duquesne Incline
- Monongahela Incline
- Monroeville Mall
- Schenley Park
- Acrisure Stadium
- Cathedral of Learning
- Children's Museum of Pittsburgh
- Point State Park
- Senator John Heinz Regional History Centre
- Carnegie Museum of Art
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
