
South Side Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, 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.

Joinery Hotel Pittsburgh, Curio Collection by Hilton
Downtown Pittsburgh
Price was CA $1,834, price is now CA $1,364 per person
CA $1,364
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Pittsburgh (PIT)
8.4/10 Very Good! (1,333 reviews)
My room had a mildewy smell, and wasn’t properly cleaned.
Reviewed on Aug. 22, 2025

Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
Price was CA $3,182, price is now CA $2,077 per person
CA $2,077
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
7.6/10 Good! (16 reviews)
Highly recommend! The property was great - with the stunning lobby, fast elevators, and clean, bright unit. Check was not required (after completing the online process & getting my code). The fully furnished apartment with lots of kitchen appliances & coffee! Bed was firm & comfortable, shower was hot with lots of pressure. It even had a washer/dryer. Great location - near restaurants & it really felt like it was connected to the city. Everyone (desk clerk, valet & manager) was friendly & helpful. Finding the parking was a challenge - I suggest calling ahead for directions to the garage.
Reviewed on Aug. 23, 2025

Hotel Indigo Pittsburgh East Liberty by IHG
East Liberty
Price was CA $2,234, price is now CA $1,535 per person
CA $1,535
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Regina (YQR) to Pittsburgh (PIT)
8.2/10 Very Good! (1,006 reviews)
Close to UPMC. Property was clean and you can walk to shopping and dining facilities.
Reviewed on Aug. 22, 2025


The Westin Pittsburgh, a Marriott Hotel
Downtown Pittsburgh
Price was CA $2,092, price is now CA $1,509 per person
CA $1,509
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
The property was great the and the sfaff were awesome.
Reviewed on Aug. 17, 2025
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 $115 per night from Sep 22 to Sep 23
CA $115
CA $131 total
Sep 22 - Sep 23
includes taxes & fees
7/10 Good! (1,003 reviews)
Needs new bedding.
"Hotel was clean but bed had sheets that should have been thrown away and replaced. Very pilled and worn. Elevator was slow. Parking should have been included with the room. Not $22 a night. Very obviously a money grab. Free breakfast was good."
Reviewed on Aug. 17, 2025

HYATT house Pittsburgh-South Side
2795 S Water St, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from Aug 31 to Sep 1
CA $198
CA $225 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Pittsburgh's Perfect Place
"When we come to Pittsburgh this is the first place we check for booking. It's dog friendly and perfect location for whatever you are doing in Pittsburgh. Lots of great walkable places to eat in the South Side. Plus if you have a dog....there is a wonderful dog park with food trucks nearby."
Reviewed on Aug. 16, 2025

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 Aug 28 to Aug 29
CA $181
CA $206 total
Aug 28 - Aug 29
includes taxes & fees
8.4/10 Very Good! (979 reviews)
Pit
"Room was good but only one night stand and they charged $30/night for oarking"
Reviewed on Aug. 21, 2025
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(67 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.

Acrisure Stadium
4.5/5(94 reviews)
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

Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers
CA $28
per traveller

Pittsburgh, PA: Sandcastle Waterpark Entry Ticket
CA $43
per adult

Private City Kickstart Tour: Tokyo
CA $186
per adult
100% of travellers recommend
Frequently asked questions
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
Expedia's Latest Trends
Hotels
- Punta Cana All Inclusive Resorts and Hotels
- Best Hotels in Rock Creek
- Golden Nugget Las Vegas Hotel & Casino
- PNC Park hotels
- Hotel Bonaparte
- Taksim Square hotels
- PPG Paints Arena hotels
- Best Hotels in New York
- Best Hotels in Vancouver
- Sri Venkateswara Temple hotels
- Dreams Los Cabos Suites Golf Resort & Spa - All Inclusive
- Hampton Inn & Suites by Hilton Lethbridge
- Best Hotels in Allegheny National Forest
- Surrey Cheap Hotels
- Iberostar Selection Cancún - All Inclusive
- Highmark Stadium hotels
- Acrisure Stadium hotels
Flights
Cruises
Packages
General
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.