South Side Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    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.
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
Oct 9 - Oct 14
found 18 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Pittsburgh (PIT)
8/10 Very Good! (2,882 reviews)
Great place to stay. Staff is friendly. Location is good.

Reviewed on Jul. 20, 2025

Hotel Indigo Pittsburgh East Liberty by IHG

Hotel Indigo Pittsburgh East Liberty by IHG

3.5 out of 5
East Liberty
Save 100% on your flight
per person
Oct 9 - Oct 14
found 18 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Pittsburgh (PIT)
8.2/10 Very Good! (1,006 reviews)
Staff were great, nice place

Reviewed on Jul. 20, 2025

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
Oct 9 - Oct 14
found 18 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Pittsburgh (PIT)
7.8/10 Good! (147 reviews)
That i had a place while doing my 1st wek at HACP

Reviewed on Jul. 12, 2025

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
Save 100% on your flight
per person
Oct 9 - Oct 14
found 18 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Pittsburgh (PIT)
8.2/10 Very Good! (1,002 reviews)
It was average at best, nothing about the property spoke out to me. The room was not up to my expectations, if not more lackluster than I would've imagined. Comes off more "pretty on the outside than inside" type vibe. Def for a one night stay than to stay for a vacation.

Reviewed on Jul. 20, 2025

Placemakr Downtown Pittsburgh

Placemakr Downtown Pittsburgh

4 out of 5
Downtown Pittsburgh
per person
Sep 11 - Sep 15
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Pittsburgh (PIT)
7.2/10 Good! (10 reviews)
Practical and accessible

Reviewed on Jul. 12, 2025

Ready to book your vacation to South Side?

 

Choose your dates

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 $163 per night from Jul 27 to Jul 28
CA $163
CA $186 total
Jul 27 - Jul 28
includes taxes & fees
8.4/10 Very Good! (955 reviews)
"Parking is to expensive"

Reviewed on Jul. 17, 2025

SpringHill Suites by Marriott Pittsburgh Southside Works
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 $164 per night from Jul 27 to Jul 28
CA $164
CA $187 total
Jul 27 - Jul 28
includes taxes & fees
8/10 Very Good! (2,912 reviews)
"Nice"

Reviewed on Jul. 18, 2025

Wyndham Grand Pittsburgh Downtown
Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
530 William Penn Place, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Aug 3 to Aug 4
CA $197
CA $224 total
Aug 3 - Aug 4
includes taxes & fees
9/10 Wonderful! (1,558 reviews)
"Spacious room, bed was very comfortable. Staff was very pleasant"

Reviewed on Jul. 19, 2025

Omni William Penn Hotel
See all 1,804 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

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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 $27
per traveller
Adventurous Scavenger Hunt in Bethlehem by Zombie Scavengers
Visit beautiful shopping and dining complex in your private tour

Private City Kickstart Tour: Tokyo

CA $185
per adult
100% of travellers recommend
Private City Kickstart Tour: Tokyo
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

CA $18
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
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 $896, 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.