South Side Vacations from ￥902,300

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The Latest South Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
per person
Apr 29 - May 5
found 20 hours ago
Roundtrip flight included
Osaka (KIX) to Pittsburgh (PIT)
7.6/10 Good! (105 reviews)
I really enjoyed staying here as it was walking distance to the paints arena, where we were going. There is other places its close to, such as downtown and mt. Washington. The property managers are very attentiveand kind and get back to you asap to address any needs you may have. I would definitely stay here again. Thank you so much Stay! Highly recommend!!

Reviewed on Mar 5, 2025

Pittsburgh Marriott City Center

Pittsburgh Marriott City Center

3.5 out of 5
Downtown Pittsburgh
per person
Apr 29 - May 5
found 20 hours ago
Roundtrip flight included
Osaka (KIX) to Pittsburgh (PIT)
8.2/10 Very Good! (1,004 reviews)
It was super close to the PPG paint arena

Reviewed on Mar 17, 2025

The Colonial Mt. Lebanon by Luxe PGH

The Colonial Mt. Lebanon by Luxe PGH

3 out of 5
Mount Lebanon
per person
Apr 29 - May 5
found 20 hours ago
Roundtrip flight included
Osaka (KIX) to Pittsburgh (PIT)
No reviews
Historic Loft Retreat With Pool

Historic Loft Retreat With Pool

3.5 out of 5
Strip District
per person
Apr 29 - May 5
found 20 hours ago
Roundtrip flight included
Osaka (KIX) to Pittsburgh (PIT)
10/10 Exceptional! (2 reviews)
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

3.5 out of 5
Downtown Pittsburgh
per person
Apr 29 - May 5
found 20 hours ago
Roundtrip flight included
Osaka (KIX) to Pittsburgh (PIT)
8/10 Very Good! (2,804 reviews)
The property is pretty and has several dining and shopping options. There is a great park for walking right across the street.

Reviewed on Mar 23, 2025

Find the Best South Side Vacation Packages

South Side Hotel Deals

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 ￥13,112 per night from Apr 1 to Apr 2
￥13,112
￥14,948 total
includes taxes & fees
Apr 1 - Apr 2
7/10 Good! (1,002 reviews)
"Amazing experience"

Reviewed on Mar 16, 2025

Holiday Inn Express Hotel & Suites Pittsburgh-South Side by IHG
HYATT house Pittsburgh-South Side
HYATT house Pittsburgh-South Side
3 out of 5
2795 S Water St, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
The price is ￥19,561 per night from Apr 2 to Apr 3
￥19,561
￥22,301 total
includes taxes & fees
Apr 2 - Apr 3
8.6/10 Excellent! (1,007 reviews)
"It’s across the street from a lot of shopping and Fun! It’s dog friendly and there is a super nice dog park right outside!"

Reviewed on Mar 23, 2025

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 ￥24,279 per night from Mar 31 to Apr 1
￥24,279
￥27,679 total
includes taxes & fees
Mar 31 - Apr 1
7.8/10 Good! (2,798 reviews)
"The property is pretty and has several dining and shopping options. There is a great park for walking right across the street."

Reviewed on Mar 23, 2025

Wyndham Grand Pittsburgh Downtown
See all 1,661 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.

Frequently asked questions

How much does a South Side vacation package cost?
Much less than you might think — from only ￥902,300, 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

PNC Park showing a city

PNC Park

4.5/5(780 reviews)

Root for the Pittsburgh Pirates at this iconic stadium, which blends a timeless ballpark atmosphere with modern amenities.

PNC Park
Oakland featuring a garden

University of Pittsburgh

4.5/5(843 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
The Gates Hillman Center is a unique building that houses the computer science program and research. I love how outside the box the building is #StunningStructures

Carnegie Mellon University

4.5/5(520 reviews)

Walk around the campus of Carnegie Mellon University, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.

Carnegie Mellon University

What to do in South Side

Admire astonishing Tokyo views in your private tour

Private City Kickstart Tour: Tokyo

￥18,758
per adult
100% of travellers recommend
Private City Kickstart Tour: Tokyo
Love in the City: Pittsburgh’s Enchanting Romantic Walk

Love in the City: Pittsburgh’s Enchanting Romantic Walk

￥32,341
per adult
Love in the City: Pittsburgh’s Enchanting Romantic Walk
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

￥1,944
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
See all activities in South Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.