South Oakland Holidays

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Your South Oakland Holiday

Packed with character and charm, South Oakland offers everything from cycling to walking. Experience the delights of this neighbourhood your way with a customized South Oakland holiday package. When it's time to explore the sights, you'll find plenty of popular attractions nearby including PNC Park, University of Pittsburgh and Carnegie Mellon University. Visit one, two (or even all!) during your trip to South Oakland. No matter what your ideal South Oakland holiday looks like, you can turn it into reality with Expedia.

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
A yellow bridge over a river with a cityscape in the background.

Downtown Pittsburgh

2 out of top 10 points of interest in this area

Abundant dining options, interesting museums and live music are just a few top things to explore in Downtown Pittsburgh. A visit to PPG Paints Arena or Benedum Center might round out your trip, and you can jump aboard the metro at Wood Street Station or Steel Plaza Station to get around town.

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A yellow bridge over a river, a weeping willow tree, and a modern building with glass windows.

North Shore

2 out of top 10 points of interest in this area

Visitors often come to North Shore for its stunning river views, but many stay to explore sights like PNC Park and Acrisure Stadium. Getting around the area on the metro is easy if you take a ride at North Side Station.

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The Mellon Institute at Carnegie Mellon University with classical columns and a Gothic cathedral in the background.

Oakland

1 out of top 10 points of interest in this area

Oakland is known for its ample dining options, and you can make a stop by Petersen Events Center and Carnegie Museum of Natural History while in the area.

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A street with a Starbucks and a plaza with colorful steps.

Strip District

Strip District is popular for its abundant dining options, and if you're looking for more to see and do, you might think about a trip to The Terminal or Senator John Heinz Regional History Centre.

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A courtyard with a fountain, brick walls, and trees.

Shadyside

Unique features of Shadyside include the restaurants and shopping. Make a stop by Walnut Street or Gallerie CHIZ while you're exploring the area.

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Top hotels in South Oakland

Hotel Indigo Pittsburgh University-Oakland by IHG

Hotel Indigo Pittsburgh University-Oakland by IHG

329 Technology Drive Pittsburgh PA
Fully refundable
£104
2 Nov - 3 Nov
includes taxes & fees
Hotel Indigo Pittsburgh University-Oakland by IHG
Wyndham Grand Pittsburgh Downtown

Wyndham Grand Pittsburgh Downtown

600 Commonwealth Pl Pittsburgh PA
Fully refundableReserve now, pay when you stay
£106
22 Oct - 23 Oct
includes taxes & fees
Wyndham Grand Pittsburgh Downtown
The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
£116
18 Oct - 19 Oct
includes taxes & fees
9.4/10 Exceptional! (2,390 reviews)
"Average"

Reviewed on 4 Oct 2026

The Landing Hotel at Rivers Casino
See all 2,005 properties in South Oakland
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 Holidays
All Inclusive Holidays
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Family Friendly Holidays
Golf Holidays
Golf Holidays
Luxury Holidays
Luxury Holidays
gay friendly holidays
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LGBTQ+ Holidays
Romantic Holidays
Romantic Holidays
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Ski Holidays
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Where to go when
Where to go when

Frequently asked questions

How much does a South Oakland travel package cost?
Get your credit card ready, because a trip to South Oakland starts from just . When you bundle your hotels, flights and car rentals into a travel package, you'll score the best deals.
If I'm not able to travel, can I cancel my South Oakland travel package?
Whether it's your hotel, flight or rental car, you can cancel or change it. Booked your South Oakland travel package in the last 24 hours? You may be able to make changes or cancellations for free. For older bookings, you may incur a fee from your airline, hotel or car rental company. For further information, browse our Customer Service Portal. We're here to help you every step of the way.
How do I get a cheap travel package to South Oakland?
One of the simplest ways to save money (and time) is to combine your bookings with Expedia. Hotels, flights, rental cars and activities — we've got everything you need. Pick the combination that suits you and see your savings grow. We know a travel package is never one-size-fits-all. That's why Expedia offers over 550 air carriers and 1,000,000 properties across the world, which lets you customize your South Oakland getaway.
Does Expedia offer Book Now, Pay Later South Oakland holidays?
Expedia has joined forces with online lender Klarna to make booking your next getaway easier on the purse strings. Paying in instalments means you can spread the costs of your next big adventure, leaving you with more cash to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find one that falls within your budget. Take a look at these flexible payment options:
  • Pay monthly holidays: Klarna has convenient monthly payment plans that work for all budgets, so you can jet away on that well-earned holiday now.
  • Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Then go for this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than all of it upfront) makes it easier to click that "book now" button, consider a low deposit holiday payment plan with Klarna.
Where should I stay in South Oakland?
Make sightseeing a breeze by staying in a hotel just around the corner from South Oakland's fantastic attractions. Acrisure Stadium and University of Pittsburgh are two which top many visitors' bucket lists.
What are the top hotels in South Oakland?
Hyatt Regency Pittsburgh International Airport and Doubletree by Hilton Pittsburgh Greentree are a couple of the most popular properties in South Oakland. Why not take a look at the facilities and amenities at each and then make a decision?
How far in advance should I book my South Oakland holiday?
Be rewarded with the biggest variety at the cheapest prices by booking your trip to South Oakland early. Air carriers typically release flights anywhere up to 12 months before departure, so start your planning ASAP. Having said that, Expedia is committed to giving you the best deals around, so it's always a good time to book your dream holiday!
What does an Expedia South Oakland travel package include?
Flights, rental cars and hotels, or any combination of them — the choice is all yours! Whether you're visiting South Oakland with the entire family or adventuring with your friends, there's a package to fit your style and budget. Once you've made your booking, why not add on one or two tours and experiences?
What should I know before booking a South Oakland travel package?
Bundling your bookings into a South Oakland travel package is the easiest way to organise your trip. Not only that, you'll save big when you combine your hotels, flights and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with a South Oakland Expedia travel package?
Yes, and with more than 550 airlines to pick from globally, you have loads of choice. Browse the available options and see which airline suits your budget and needs.

Stay near popular South Oakland attractions

Pittsburgh Playhouse

You can get tickets for a performance at Pittsburgh Playhouse during your stay in Pittsburgh. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.
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Things to do

Picture 4 for Activity Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

£22
per adult
86% 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

£10
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
This tour is the best tour for sports fans! Big fun guaranteed!

Black & Gold Pittsburgh History Tour for Sports Fans

£24
per adult
Black & Gold Pittsburgh History Tour for Sports Fans
See all activities in Pittsburgh

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.