South Side Vacations from ￥287,015

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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
Price was ￥369,293, price is now ￥287,015 per person
￥287,015
per person
Sep 26 - Oct 1
found 4 hours ago
Roundtrip flight included
Tokyo (TYO) to Pittsburgh (PIT)
8/10 Very Good! (302 reviews)
Affordable

Reviewed on Jul 4, 2026

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was ￥480,272, price is now ￥360,032 per person
￥360,032
per person
Sep 26 - Oct 1
found 4 hours ago
Roundtrip flight included
Tokyo (TYO) to Pittsburgh (PIT)
8.6/10 Excellent! (1,000 reviews)
It was just ok. Maybe Pittsburgh needs to get a Ritz or Four Seasons.

Reviewed on Jun 24, 2026

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was ￥347,894, price is now ￥288,219 per person
￥288,219
per person
Sep 26 - Oct 1
found 4 hours ago
Roundtrip flight included
Tokyo (TYO) 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 ￥355,265, price is now ￥294,752 per person
￥294,752
per person
Sep 26 - Oct 1
found 4 hours ago
Roundtrip flight included
Tokyo (TYO) 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

Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
Downtown Pittsburgh
Price was ￥496,434, price is now ￥413,418 per person
￥413,418
per person
Sep 26 - Oct 1
found 4 hours ago
Roundtrip flight included
Tokyo (TYO) to Pittsburgh (PIT)
8.8/10 Excellent! (1,008 reviews)
It was a beautiful experience

Reviewed on Jul 11, 2026

Find the Best South Side Vacation Packages

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 ￥18,354 per night from Aug 9 to Aug 10
￥18,354
￥20,924 total
Aug 9 - Aug 10
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 ￥14,034 per night from Aug 2 to Aug 3
￥14,034
￥16,000 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 ￥21,681 per night from Jul 19 to Jul 20
￥21,681
￥24,717 total
Jul 19 - Jul 20
includes taxes & fees
8.2/10 Very Good! (3,635 reviews)
"Great lication to stadium"

Reviewed on Jul 12, 2026

Wyndham Grand Pittsburgh Downtown
See all 2,030 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.

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

￥7,842
per adult
100% of travellers recommend
Pittsburgh Pirates Baseball Game at PNC Park
Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

￥4,714
per adult
90% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl

￥2,126
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 ￥287,015, 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.

Explore a world of travel with Expedia

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