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.
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
Downtown Pittsburgh
Price was CA $872, price is now CA $762 per person
CA $762
per person
Aug 21 - Aug 23
found 23 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Pittsburgh (PIT)
8.6/10 Excellent! (1,551 reviews)
Check in could have went better.

Reviewed on Jul 12, 2026

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was CA $1,793, price is now CA $1,412 per person
CA $1,412
per person
Sep 11 - Sep 14
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Pittsburgh (PIT)
8/10 Very good! (302 reviews)
Affordable

Reviewed on Jul 4, 2026

Crowne Plaza Suites Pittsburgh South by IHG

Crowne Plaza Suites Pittsburgh South by IHG

3.5 out of 5
Price was CA $1,275, price is now CA $1,095 per person
CA $1,095
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Pittsburgh (PIT)
8.8/10 Excellent! (1,000 reviews)
Pool and surrounding area is in need of repair, tiles missing, cement cracked, pool was dirty and needed vacuumed/swept. Room was sub-par. Bathroom had patched ceiling and peeling wallpaper near the shower. I found a bug in my son’s bed also.

Reviewed on Jul 12, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was CA $1,694, price is now CA $1,458 per person
CA $1,458
per person
Sep 11 - Sep 14
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Pittsburgh (PIT)
8.6/10 Excellent! (146 reviews)
Property is a beautiful, historic building in a convenient location off the freeway. Our rooms were spacious, clean, and comfortable with the exception of no central air. A loud, mobile air unit was in two of the rooms. The blinds in one room could not close because of a missing wand. Also the roku was not working. Keep in mind hotel room is near train tracks. Staff was kind enough to meet us at the parking area door to let us into the building so that we could conveniently check in (some parking is near an amtrak station).

Reviewed on Jul 10, 2026

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown

4 out of 5
Downtown Pittsburgh
Price was CA $1,776, price is now CA $1,549 per person
CA $1,549
per person
Sep 11 - Sep 14
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Pittsburgh (PIT)
8.4/10 Very good! (1,078 reviews)
Shower was Luke warm, toilets didn’t flush right, sink dint drain properly.

Reviewed on Jul 12, 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
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Aug 3 to Aug 4
CA $161
CA $183 total
Aug 3 - Aug 4
includes taxes & fees
8.6/10 Excellent! (1,020 reviews)
"Great location on the south side. Would stay here again when rates are reasonable."

Reviewed on Jul 12, 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 $123 per night from Aug 2 to Aug 3
CA $123
CA $140 total
Aug 2 - Aug 3
includes taxes & fees
7.8/10 Good! (1,014 reviews)
"Good"

Reviewed on Jul 11, 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 $188 per night from Jul 28 to Jul 29
CA $188
CA $214 total
Jul 28 - Jul 29
includes taxes & fees
8.2/10 Very good! (3,636 reviews)
"Great lication to stadium"

Reviewed on Jul 12, 2026

Wyndham Grand Pittsburgh Downtown
See all 2,037 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

Pittsburgh Pirates Baseball Game at PNC Park

Pittsburgh Pirates Baseball Game at PNC Park

CA $79
per adult
Pittsburgh Pirates Baseball Game at PNC Park
Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

CA $41
per adult
90% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
This tour is the best tour for sports fans! Big fun guaranteed!

Black & Gold Pittsburgh History Tour for Sports Fans

CA $46
per adult
Black & Gold Pittsburgh History Tour for Sports Fans
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 $762, 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.

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