South Side Vacation Packages
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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 $1,140, price is now CA $967 per person
CA $967
per person
Jul 10 - Jul 14
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
6.6/10 (1,007 reviews)
Room was clean , close to airport . Staff very friendly.
Reviewed on May 21, 2026
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Price was CA $1,983, price is now CA $1,527 per person
CA $1,527
per person
Jul 10 - Jul 14
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
It’s a nice hotel with friendly staff. I think you should give a discount or free parking for people staying at the hotel. The cost to parks adds up quick.
Reviewed on Apr 10, 2026
Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
Price was CA $1,321, price is now CA $1,080 per person
CA $1,080
per person
Jul 10 - Jul 14
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.4/10 Very Good! (1,492 reviews)
Convenient location w nice room.
Reviewed on May 19, 2026
Wyndham Grand Pittsburgh Downtown
Downtown Pittsburgh
Price was CA $1,245, price is now CA $1,056 per person
CA $1,056
per person
Jul 10 - Jul 14
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.2/10 Very Good! (3,551 reviews)
The hotel is ideally located, and the view of the rivers was spectacular. Everything that mattered to us was within walking distance. I’d be pleased to stay at the Wyndham again.
Reviewed on May 23, 2026
The Maverick by Kasa
East Liberty
Price was CA $1,414, price is now CA $1,205 per person
CA $1,205
per person
Jul 10 - Jul 14
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
9/10 Wonderful! (961 reviews)
Will def come back xx Was in the fifth floor amazing view. Just hope next time the windows will be able to be opened. Xx fab location amenities staff building area food. So lovely.
Reviewed on May 20, 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 $120 per night from Jun 1 to Jun 2
CA $120
CA $137 total
Jun 1 - Jun 2
includes taxes & fees
7.6/10 Good! (1,000 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 May 28 to May 29
CA $181
CA $206 total
May 28 - May 29
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Clean room. Nice staff."
Reviewed on May 20, 2026
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Jun 21 to Jun 22
CA $217
CA $247 total
Jun 21 - Jun 22
includes taxes & fees
8.2/10 Very Good! (3,548 reviews)
"The hotel is ideally located, and the view of the rivers was spectacular. Everything that mattered to us was within walking distance. I’d be pleased to stay at the Wyndham again."
Reviewed on May 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.
Discover the most popular places to visit in South Side
PNC Park
4.5/5(69 reviews)
Root for the Pittsburgh Pirates at this iconic stadium, which blends a timeless ballpark atmosphere with modern amenities.
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.
PPG Paints Arena
5/5(81 reviews)
Catch an event at PPG Paints Arena during your trip to Pittsburgh. Experience the acclaimed theater scene or attend a sporting event in this vibrant area.
What to do in South Side
Pittsburgh: Museum of Illusions Entrance Ticket
CA $40
per adult
80% of travellers recommend
New! Black & Gold Sports History Tour for Sports Fans
CA $45
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
CA $18
per adult
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- 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.
