South Side Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top South Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was CA $1,437, price is now CA $1,194 per person
CA $1,194
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.6/10 Excellent! (146 reviews)
Right near the bus terminal so it can get sketchy walking around. Loved the washer and dryer in the room. Heads up to bring unscented detergent if fragrances bother you.

Reviewed on Jul 2, 2026

Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Price was CA $1,631, price is now CA $1,363 per person
CA $1,363
per person
Aug 26 - Sep 1
found 9 hours ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Pittsburgh (PIT)
8/10 Very good! (1,006 reviews)
As a Platinum member of IHG, this hotel is ever the most ridiculous experience. I arrived and received a looks cleaned room. However, there is some sort of marks and scraps on bed and unknown liquid mark on hair drying, only one set of towel and unknown hair on toilet seat, as well no coffee machine and chair. Though the staff give me a room change, it’s basically nothing offered for a such unsatisfied experience especially as a member of the IHG.

Reviewed on Jun 30, 2026

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

4 out of 5
Downtown Pittsburgh
Price was CA $1,671, price is now CA $1,399 per person
CA $1,399
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.2/10 Very good! (1,074 reviews)
good location, average and old facility

Reviewed on Jul 1, 2026

Hampton Inn & Suites Cranberry Pittsburgh

Hampton Inn & Suites Cranberry Pittsburgh

2.5 out of 5
Price was CA $1,711, price is now CA $1,435 per person
CA $1,435
per person
Aug 26 - Sep 1
found 9 hours ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Pittsburgh (PIT)
9/10 Wonderful! (1,005 reviews)
Overall room is good. Bathroom silicon caulk has black mold. Not sure if their maintenance group know what todo…possibly all bathrooms in this having the same issue of mold on silicon. Breakfast is seems average only.

Reviewed on Jun 30, 2026

Hilton Garden Inn Pittsburgh Downtown

Hilton Garden Inn Pittsburgh Downtown

3 out of 5
Downtown Pittsburgh
Price was CA $2,192, price is now CA $1,843 per person
CA $1,843
per person
Aug 26 - Sep 1
found 9 hours ago
Roundtrip non-stop flight included
Saskatoon (YXE) to Pittsburgh (PIT)
9/10 Wonderful! (1,377 reviews)
Clean and nice

Reviewed on Jul 2, 2026

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South Side Hotel Deals

SpringHill Suites by Marriott Pittsburgh Southside Works

SpringHill Suites by Marriott Pittsburgh Southside Works

3 out of 5
2950 S Water St Pittsburgh PA
The price is CA $149 per night from Aug 2 to Aug 3
CA $149
CA $170 total
Aug 2 - Aug 3
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"A terrible disgusting experience. Do NOT stay here! When we checked in to our room, we went to the bathroom and saw the disgusting mess. The toilet handle was broken off. The bowl was filled with toilet paper and dirty water. When we complained to the front desk, they said they could not fix it and ..."

Reviewed on Jul 3, 2026

SpringHill Suites by Marriott Pittsburgh Southside Works
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 $132 per night from Aug 2 to Aug 3
CA $132
CA $151 total
Aug 2 - Aug 3
includes taxes & fees
7.8/10 Good! (1,001 reviews)
"Your hotel would have been excellent if only the elevator had been a little faster (it is clearly very old) and the housekeeping staff on our floor had done their job properly. We left our room at 11:00 a.m. and returned around 10:00–11:00 p.m. Unfortunately, the "light service" that had been promised ..."

Reviewed on Jul 2, 2026

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

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Jul 9 to Jul 10
CA $190
CA $217 total
Jul 9 - Jul 10
includes taxes & fees
8.2/10 Very good! (3,598 reviews)
"Didnt try restaurant for breakfast. Bar was great for dinner and drink"

Reviewed on Jul 3, 2026

Wyndham Grand Pittsburgh Downtown
See all 2,042 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.
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Stay near popular South Side attractions

Rex Theater

6.0/10 (1 review)
You can get tickets for a performance at Rex Theater on your trip to Pittsburgh. Check out the shops and top-notch restaurants in this family-friendly area.
See properties

What to do in South Side

Picture 4 for Activity Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

CA $40
per adult
80% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
Make new friends as you learn the exciting history of whiskey in Pittsburgh

Whiskey Rebellion & Prohibition Tour

CA $68
per adult
Whiskey Rebellion & Prohibition Tour
Pittsburgh: Beauty of the Burgh Bike Tour

Pittsburgh: Beauty of the Burgh Bike Tour

CA $82
per adult
94% of travellers recommend
Pittsburgh: Beauty of the Burgh Bike Tour
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 $1,194, 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.