South Side Vacation Packages
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Top South Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh
Downtown Pittsburgh
Price was CA $1,276, price is now CA $1,045 per person
CA $1,045
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8/10 Very Good! (280 reviews)
This was a perfect arrangement for our short visit to Pittsburgh. Clean and functional.
Reviewed on May 20, 2026
The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Price was CA $1,734, price is now CA $1,368 per person
CA $1,368
per person
Jul 16 - Jul 19
found 1 day 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
Crowne Plaza Suites Pittsburgh South by IHG
Price was CA $1,342, price is now CA $1,134 per person
CA $1,134
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
8.8/10 Excellent! (1,000 reviews)
Morgan @ the front desk was amazing!
Her interaction with us was always so positive & helpful. She’s a gem!
Reviewed on May 20, 2026
Renaissance Pittsburgh Hotel
Downtown Pittsburgh
Price was CA $1,339, price is now CA $1,164 per person
CA $1,164
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Pittsburgh (PIT)
9/10 Wonderful! (1,011 reviews)
The view from riverside is priceless
Reviewed on May 17, 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 $114 per night from May 25 to May 26
CA $114
CA $130 total
May 25 - May 26
includes taxes & fees
7.6/10 Good! (1,024 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 $168 per night from May 26 to May 27
CA $168
CA $192 total
May 26 - May 27
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 $236 per night from Jun 21 to Jun 22
CA $236
CA $270 total
Jun 21 - Jun 22
includes taxes & fees
8.2/10 Very Good! (3,540 reviews)
"Room 438 is located next to the pool and spa. Doors start slamming before 6am. Forget sleeping later than that. Avoid the fourth floor with rooms higher than 420 at all costs unless you like swimming or working out at 6am. Also, the bathrooms have no ventilation. They have a clunky barn door with ..."
Reviewed on May 21, 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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- 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.
