South Oakland Vacations
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Where to stay in South Oakland
Find the best South Oakland areas and neighborhoods for the activities you enjoy most. Learn more about South Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
North Shore
2 out of top 10 points of interest in this area
Heinz Field, PNC Park, and The Andy Warhol Museum await in this vibrant area, connected to Downtown Pittsburgh by the iconic Roberto Clemente, Andy Warhol, and Rachel Carson Bridges. Enjoy easy access to two light rail stations.
Oakland
1 out of top 10 points of interest in this area
Academic and healthcare hub, Oakland boasts museums, shopping venues, and diverse dining options along Forbes and Fifth Avenue. Explore historic districts and easily navigate the area via the distinctive city steps and public transportation.
Strip District
Brimming with specialty shops, unique boutiques, and ethnic food purveyors, the Strip District offers a lively atmosphere with art studios, antique dealers, and the historic St. Stanislaus Kostka Church. Enjoy open-air markets and vibrant nightlife during summer months.
Shadyside
Victorian mansions and modern apartments create a diverse residential atmosphere. Explore upscale stores on Walnut Street, dine at local eateries like Pamela's Diner, and easily walk between the three business corridors. Public transportation is accessible.
South Oakland Hotel Deals
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
Fully refundable
₩161,645
₩184,283 total
Nov 2 - Nov 3
includes taxes & fees
Wyndham Grand Pittsburgh Downtown
600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
₩165,760
₩188,966 total
Oct 22 - Oct 23
includes taxes & fees
The Landing Hotel at Rivers Casino
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
₩179,941
₩205,133 total
Oct 18 - Oct 19
includes taxes & fees
9.4/10 Exceptional! (2,400 reviews)
"It was my first time staying there, the hotel is really nice, it was the day of a Steelers game so the parking experience was very interesting. If the valet parking service is full then you can self park but make sure to drop your bags off with the valet before heading up to the self park in the ..."
Reviewed on Oct 6, 2026
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 Oakland vacation package cost?
From as low as . Yes, you read that correctly. Our South Oakland packages are a simple way to make your dollar go further. Combine your favorite flights, hotels and rental car and discover this top destination.
How do I get a cheap travel package to South Oakland?
It's easy. Just bundle everything together. Hotels, flights and rental cars — combine whatever you need into a South Oakland vacation package to save a ton of cash. Score even better deals when you add extras such as activities or tours to your booking. But that's not the only impressive part. You have the freedom to customize your vacation your own way. We offer more than 550 partner airlines and 1,000,000 properties across the world, so that everyone has a chance to travel and live out those vacation dreams.
Where should I stay in South Oakland?
Most visitors to South Oakland put both Acrisure Stadium and PNC Park on their to-do lists. Why not select a hotel right near these popular attractions?
What are the top hotels in South Oakland?
Hotel Indigo Pittsburgh University-Oakland, an IHG Hotel and Hampton Inn Pittsburgh University/Medical Center are a couple of the most popular hotels in South Oakland. Why not check out the rates and facilities at each and then decide?
How far in advance should I book my South Oakland vacation?
Your best bet is to book early. Air carriers typically advertise flights around a year prior to departure, and this is an ideal opportunity to score some of the cheapest prices. Boss just told you to take your vacation time next month? That's alright! Expedia are never short on fantastic deals to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia South Oakland travel package include?
Rental cars, flights and hotels, or any combination of the three — it's up to you! Whether you're exploring South Oakland with the family or enjoying a solo break, there's a package to fit your budget and style. Once you've made your booking, why not add on some tours and experiences?
What should I know before booking a South Oakland travel package?
Locking in all the parts of your escape together is one of the easiest ways to save. Combine car rentals, airfares and hotels into a handy package. But you're not limited to hotels. Expedia has all sorts of properties, including vacation rentals such as beach villas and short-term homes. You've got loads of choices!
Can I choose my airline with a South Oakland Expedia vacation package?
Yes, you can. We have more than 550 partner airlines worldwide, so choose the carrier that suits your budget and travel needs.
If I'm not able to travel, can I cancel my South Oakland vacation package?
Don't stress if you're rethinking your South Oakland vacation package — you can cancel or change your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We totally get that life can occasionally throw a spanner in the travel works, so look up our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.
Stay near popular South Oakland attractions
Pittsburgh Playhouse
You can make plans for a show at Pittsburgh Playhouse during your trip to Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.