South Side Vacation Packages

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    Save up to CA $1,096 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.
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
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

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
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

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
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

Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
Downtown Pittsburgh
Price was CA $3,668, price is now CA $2,611 per person
CA $2,611
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
8.8/10 Excellent! (1,000 reviews)
Everything was great

Reviewed on Aug. 12, 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
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

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South Side Hotel Deals

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG

2.5 out of 5
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

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG
HYATT house Pittsburgh-South Side

HYATT house Pittsburgh-South Side

3 out of 5
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

HYATT house Pittsburgh-South Side
SpringHill Suites by Marriott Pittsburgh Southside Works

SpringHill Suites by Marriott Pittsburgh Southside Works

3 out of 5
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

SpringHill Suites by Marriott Pittsburgh Southside Works
See all 1,779 properties in South Side
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.
All Inclusive Vacations
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Discover the most popular places to visit in South Side

PNC Park which includes a city

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.

PNC Park
University of Pittsburgh

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.

University of Pittsburgh
Acrisure Stadium

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.

Acrisure Stadium

What to do in South Side

Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers

Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers

CA $28
per traveller
Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers
Pittsburgh, PA: Sandcastle Waterpark Entry Ticket

Pittsburgh, PA: Sandcastle Waterpark Entry Ticket

CA $43
per adult
Pittsburgh, PA: Sandcastle Waterpark Entry Ticket
Visit beautiful shopping and dining complex in your private tour

Private City Kickstart Tour: Tokyo

CA $186
per adult
100% of travellers recommend
Private City Kickstart Tour: Tokyo
See all activities in South Side

Frequently asked questions

How much does a South Side vacation package cost?
Much less than you might think — from only CA $1,364, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.