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*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top South Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Americas Best Value Inn Pittsburgh Airport
Price was CA $1,313, price is now CA $1,064 per person
CA $1,064
per person
Jul 2 - Jul 8
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Pittsburgh (PIT)
6.6/10 (1,001 reviews)
Room was clean , close to airport . Staff very friendly.
Reviewed on May 21, 2026
The Oaklander Hotel, Autograph Collection
Oakland
Price was CA $2,440, price is now CA $2,049 per person
CA $2,049
per person
Aug 20 - Aug 25
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
9.2/10 Wonderful! (777 reviews)
Great hotel, great staff, and great location.
Reviewed on May 26, 2026
Hotel Indigo Pittsburgh East Liberty by IHG
East Liberty
Price was CA $1,506, price is now CA $1,310 per person
CA $1,310
per person
Aug 20 - Aug 25
found 10 hours ago
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
8/10 Very Good! (1,006 reviews)
The staff (especially the young lady at the front desk) were excellent. The room was clean and the breakfast was delicious! I only had the room for one night, but location was great and I would definitely recommend this property.
Reviewed on May 22, 2026
DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
Downtown Pittsburgh
Price was CA $1,322, price is now CA $1,167 per person
CA $1,167
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Moncton (YQM) to Pittsburgh (PIT)
8.2/10 Very Good! (1,062 reviews)
Booked this for the pool and central location. It was great to be inside swimming around, watching all the people coming & going from PPG arena, lol! The hotel is close to everything, a short walk (highly recommend The Speckled Egg in the Union Trust Building. Delicious brunch and coffee, wow!) or you can catch a bus to explore further out. Hotel is clean, nice room. Got an upgrade with living room, it was gigantic! So very nice to spread out. Fairly quiet for being downtown. Friendly staff. ++++ for the cookies!
Reviewed on May 24, 2026
South Side Hotel Deals
Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG
20 S 10th St Pittsburgh PA
Fully refundable
The price is CA $129 per night from Jun 1 to Jun 2
CA $129
CA $147 total
Jun 1 - Jun 2
includes taxes & fees
7.8/10 Good! (1,004 reviews)
"I had to find a place to stay that was close to the hospital. I came upon this hotel and was so thankful we did! They were more than nice at the front desk. Very friendly people. The bed was the most comfortable bed ever!"
Reviewed on May 21, 2026
SpringHill Suites by Marriott Pittsburgh Southside Works
2950 S Water St Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $181 per night from Jun 14 to Jun 15
CA $181
CA $207 total
Jun 14 - Jun 15
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"The room was perfect and spacious."
Reviewed on May 25, 2026
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $219 per night from Jun 21 to Jun 22
CA $219
CA $249 total
Jun 21 - Jun 22
includes taxes & fees
8.2/10 Very Good! (3,553 reviews)
"Great stay and they were accommodating when we needed a roll away bed."
Reviewed on May 28, 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.
Discover the most popular places to visit in South Side
PNC Park
Root for the Pittsburgh Pirates at this iconic stadium, which blends a timeless ballpark atmosphere with modern amenities.
University of Pittsburgh
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
Giant ketchup bottles tilt onto the scoreboard to celebrate touchdowns in this innovative riverside football arena at the heart of Pittsburgh sports.
What to do in South Side
Pittsburgh: Museum of Illusions Entrance Ticket
CA $40
per adult
80% of travellers recommend
Pittsburgh: Beauty of the Burgh Bike Tour
CA $81
per adult
94% of travellers recommend
Explore a world of travel with Expedia
- 5 Star Hotels in Arlington
- 5 Star Hotels in Knoxville
- 5 Star Hotels in St. Clair
- Hotels near Acrisure Stadium
- B&B in Allegheny County
- Cabin Rentals in Allegheny County
- Inns in Allegheny County
- Beach Hotel Hotels in Allentown
- Boutique Hotels in Allentown
- Golf Hotels in Allentown
- Historic Hotels in Allentown
- Hotels with Bar in Allentown
- Hotels with Hot Tubs in Allentown
- Hotels with Kitchenettes in Allentown
- Hotels with smoking rooms in Allentown
- Pet-Friendly Hotels in Allentown
- Spa Hotels in Allentown
- Waterpark Hotels in Allentown
- Allentown Hotels
- Hotel Wedding Venues Hotels in Arlington
- Bluff Hotels
- Crawford-Roberts Hotels
- Family Hotels in Allegheny County
- Golf Hotels in Allegheny County
- Historic Hotels in Allegheny County
- Hotels with Free Airport Shuttle in Allegheny County
- Hotels with Free Breakfast in Allegheny County
- Hotels with Hot Tubs in Allegheny County
- Luxury Hotels in Allegheny County
- Pet-Friendly Hotels in Allegheny County
- Ski Hotels in Allegheny County
- Spa Hotels in Allegheny County
- Allegheny County Hotels
- Downtown Pittsburgh Hotels
- Hotels near Duquesne University
- Hotels near First Avenue Station
- Hotels with Hot Tubs in Knoxville
- Hotels with an Indoor Pool in Knoxville
- Hotels with Kitchenettes in Knoxville
- Pet-Friendly Hotels in Knoxville
- Knoxville Hotels
- Golf Hotels in Mount Oliver
- Luxury Hotels in Mount Oliver
- Mount Oliver Hotels
- Hotels near PNC Park
- Hotels near PPG Paints Arena
- Cheap Hotels in Pittsburgh
- Pittsburgh Hotels
- Hotels near Rex Theater
- South Oakland Hotels
- Cheap Hotels in South Side Flats
- Hotels with Early Check-in in South Side Flats
- Hotels with Waterslides in South Side Flats
- Pet-Friendly Hotels in South Side Flats
- Spa Hotels in South Side Flats
- South Side Flats Hotels
- Hotels with Bar in South Side Slopes
- Hotels with smoking rooms in South Side Slopes
- Romantic Hotels in South Side Slopes
- Waterpark Hotels in South Side Slopes
- South Side Slopes Hotels
- St. Clair Hotels
- Terrace Village Hotels
- Acrisure Stadium
- Andy Warhol Museum
- Carnegie Mellon University
- Carnegie Museum and Library
- Carnegie Museum of Art
- Carnegie Museum of Natural History
- Carnegie Science Center
- Cathedral of Learning
- Children's Museum of Pittsburgh
- Duquesne Incline
- Heinz Hall
- Kennywood
- Manor Theatre
- Market Square
- Monongahela Incline
- Mount Washington Vacations
- National Aviary
- North Side Vacations
- Pnc Park
- Ppg Paints Arena
- Phipps Conservatory
- Visit Bluff
- Visit Downtown Pittsburgh
- Visit South Side Flats
- Visit Terrace Village
- Pittsburgh Vacations
- Visit Pittsburgh
- Point State Park
- Roberto Clemente Bridge
- Schenley Park
- Senator John Heinz Regional History Centre
- Southwest Pennsylvania Vacations
- The Waterfront
- Upmc Shadyside
- University of Pittsburgh
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
