South Side Vacation Packages

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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
per person
Jun. 29 - Jul. 1
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
7.6/10 Good! (2,721 reviews)
We enjoyed staying at this place. Very beautiful city. A lot of places to eat

Reviewed on May 13, 2024

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
per person
Jun. 29 - Jul. 1
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
7.6/10 Good! (42 reviews)
Great staff and management. Extremely clean property. In the middle of downtown!

Reviewed on Apr. 30, 2024

Homewood Suites by Hilton Pittsburgh Downtown

Homewood Suites by Hilton Pittsburgh Downtown

3 out of 5
Downtown Pittsburgh
per person
Jun. 29 - Jul. 1
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
9/10 Wonderful! (1,004 reviews)
Check in was great! It was within walking distance of shops and restaurants.

Reviewed on May 14, 2024

Etage Executive Living

Etage Executive Living

3.5 out of 5
Downtown Pittsburgh
per person
Jun. 29 - Jul. 1
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
9/10 Wonderful! (853 reviews)
Great hotel for families. It is not Ritz but excellent. I had a corner 2 bedroom. The shades do not seal., but they can darken the windows. Lots of windows and great views. There are street noises.

Reviewed on May 13, 2024

Wyndham Pittsburgh University Center

Wyndham Pittsburgh University Center

3.5 out of 5
Oakland
per person
Jun. 29 - Jul. 1
Roundtrip flight included
Toronto (YYZ) to Pittsburgh (PIT)
7.6/10 Good! (1,304 reviews)
Front desk staff distracted andtalking to other staff when checking in. However they were friendly. Would like to have had hot water and coffee more easily accessible in the lobby

Reviewed on May 14, 2024

Where to stay in South Side

Find the best South Side areas and neighborhoods for the activities you enjoy most. Learn more about South Side
South Shore showing a city, landscape views and a river or creek

Mount Washington

Consider a visit to Patrick Fagan Overlook and take some time to enjoy the abundant dining options during your time in Mount Washington. If you want to see more of the city, jump on the metro at South Hills Junction Station or Palm Garden Station.

Find hotel + flight trips in Mount Washington

South Side Hotel Deals

Holiday Inn Express Hotel & Suites Pittsburgh-South Side, an IHG Hotel
Holiday Inn Express Hotel & Suites Pittsburgh-South Side, an IHG Hotel
2.5 out of 5
20 S 10th St, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from May 19 to May 20
CA $126
CA $144 total
includes taxes & fees
May 19 - May 20
7/10 Good! (973 reviews)
"Hhhhhj"

Reviewed on May 15, 2024

Holiday Inn Express Hotel & Suites Pittsburgh-South Side, an IHG Hotel
HYATT house Pittsburgh-South Side
HYATT house Pittsburgh-South Side
3 out of 5
2795 S Water St, Pittsburgh, PA
Fully refundable
The price is CA $190 per night from May 22 to May 23
CA $190
CA $217 total
includes taxes & fees
May 22 - May 23
8.8/10 Excellent! (999 reviews)
"Great"

Reviewed on May 15, 2024

HYATT house Pittsburgh-South Side
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 $202 per night from May 23 to May 24
CA $202
CA $230 total
includes taxes & fees
May 23 - May 24
7.4/10 Good! (2,718 reviews)
"We enjoyed staying at this place. Very beautiful city. A lot of places to eat"

Reviewed on May 13, 2024

Wyndham Grand Pittsburgh Downtown
See all 1,584 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a South Side vacation package cost?
Much less than you might think — from only CA $720, 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.

Discover the most popular places to visit in South Side

Image for PNC Park

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
Image for 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
Image for 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

What to do in South Side

Image for Scavenger Hunt Adventure in Bethlehem by Operation City Quest

Scavenger Hunt Adventure in Bethlehem by Operation City Quest

CA $14
Per adult
Scavenger Hunt Adventure in Bethlehem by Operation City Quest
See all activities in South Side

Other vacations you might like

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