South Side Vacation Packages

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Top South Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Maverick by Kasa

The Maverick by Kasa

3 out of 5
East Liberty
per person
Aug. 18 - Aug. 23
found 11 hours ago
Roundtrip flight included
Montreal (YUL) to Pittsburgh (PIT)
8.6/10 Excellent! (350 reviews)
The historic architect remains, nice sleek decor design nice staff.

Reviewed on May 27, 2024

Omni William Penn Hotel

Omni William Penn Hotel

4 out of 5
Downtown Pittsburgh
per person
Aug. 18 - Aug. 23
found 17 hours ago
Roundtrip flight included
Montreal (YUL) to Pittsburgh (PIT)
9/10 Wonderful! (1,326 reviews)
No clear smoking area. Shower set up was cheap looking for such a beautiful hotel.

Reviewed on May 28, 2024

Wyndham Pittsburgh University Center

Wyndham Pittsburgh University Center

3.5 out of 5
Oakland
per person
Aug. 18 - Aug. 23
found 11 hours ago
Roundtrip flight included
Montreal (YUL) to Pittsburgh (PIT)
7.6/10 Good! (1,304 reviews)
Property was under construction so a few hiccups in the area of on site dining and occasional elevator issues. Staff was accommodating.

Reviewed on May 28, 2024

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
per person
Aug. 18 - Aug. 23
found 17 hours ago
Roundtrip flight included
Montreal (YUL) to Pittsburgh (PIT)
8.4/10 Very Good! (1,001 reviews)
The convenience of having the Marriott next to arena was great. Access from the parkway off the exit was simply the best . Decreases the travel time and eliminates stress in avoiding city traffic. The staff at the hotel were very nice and check in efficient and took very little time. The hotel room was old and could use a face lift . It was very clean .! All in all it was a great experience staying at this hotel site.

Reviewed on May 26, 2024

EVEN Hotel Pittsburgh Downtown, an IHG Hotel

EVEN Hotel Pittsburgh Downtown, an IHG Hotel

4 out of 5
Downtown Pittsburgh
per person
Aug. 18 - Aug. 23
found 17 hours ago
Roundtrip flight included
Montreal (YUL) to Pittsburgh (PIT)
8.4/10 Very Good! (1,002 reviews)
Very convenient location downtown. A little beat up but pretty clean. Staff was very courteous. Cute little bar area too.

Reviewed on May 27, 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 $138 per night from May 29 to May 30
CA $138
CA $157 total
includes taxes & fees
May 29 - May 30
7/10 Good! (1,015 reviews)
"Convienent. Safe. 2 bits of feedback- bed was STIFF and pool was slippery. Both of us nearly fell"

Reviewed on May 23, 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 $191 per night from Jun. 16 to Jun. 17
CA $191
CA $217 total
includes taxes & fees
Jun 16 - Jun 17
8.8/10 Excellent! (1,001 reviews)
"The hotel wasn’t in good shape for a Hyatt. You can’t walk outside from the lobby, you have to go down to parking floor to exit. Strange setup. Why can’t thes fancy named hotels afford a $500 smart tv? None of the hotels offer that option. It’s very strange to me. If you charge $200 a night, you ..."

Reviewed on May 20, 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 $196 per night from May 29 to May 30
CA $196
CA $223 total
includes taxes & fees
May 29 - May 30
7.4/10 Good! (2,725 reviews)
"Fantastic location, walkable to a lot of restaurants and the stadiums. We had a beautiful view of the river. The only complaint was the hotel was extremely busy the weekend and we had to wait in long lines for the elevator. Walls seemed thin too, we could hear our neighbors alarm clock."

Reviewed on May 27, 2024

Wyndham Grand Pittsburgh Downtown
See all 1,568 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

Frequently asked questions

How much does a South Side vacation package cost?
Much less than you might think — from only CA $943, 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 Pittsburgh's Hidden Treasures Tour

Pittsburgh's Hidden Treasures Tour

CA $68
Per adult
Pittsburgh's Hidden Treasures Tour
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.