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
Downtown Pittsburgh

Downtown Pittsburgh

2 out of top 10 points of interest in this area
4.5/5(15 area reviews)

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.

Find hotels in Downtown Pittsburgh

Top hotels in South Oakland

Hotel Indigo Pittsburgh University-Oakland by IHG

Hotel Indigo Pittsburgh University-Oakland by IHG

3.5 out of 5
329 Technology Drive Pittsburgh PA
Fully refundable
The price is £113 per night from 18 May to 19 May
£113
18 May - 19 May
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Very clean Complimentary coffee in lobby Didn’t like that had to pay additional fee to park

Reviewed on 13 Apr 2026

Hotel Indigo Pittsburgh University-Oakland 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 £126 per night from 21 Apr to 22 Apr
£126
21 Apr - 22 Apr
includes taxes & fees
Wyndham Grand Pittsburgh Downtown
Joinery Hotel Pittsburgh, Curio Collection by Hilton

Joinery Hotel Pittsburgh, Curio Collection by Hilton

4 out of 5
453 Boulevard of the Allies Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is £116 per night from 27 Apr to 28 Apr
£116
27 Apr - 28 Apr
includes taxes & fees
8.4/10 Very Good! (1,475 reviews)
A beautiful hotel with great views. The staff was attentive and everything was very clean. Great stay and convenient location.

Reviewed on 15 Apr 2026

Joinery Hotel Pittsburgh, Curio Collection by Hilton
See all 2,025 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

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.

Popular places to visit

University of Pittsburgh in Pittsburgh, PA

University of Pittsburgh

Explore the campus of University of Pittsburgh, a top university in Pittsburgh. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

University of Pittsburgh
PPG Paints Arena

PPG Paints Arena

Catch an event at PPG Paints Arena during your trip to Pittsburgh. Experience the acclaimed theatre scene or attend a sporting event in this vibrant area.

PPG Paints Arena
Kennywood

Kennywood

Spend a fun-filled day making your way between over 30 rides and attractions in one of the oldest continually running amusement parks in the United States.

Kennywood

Things to do

Pittsburgh: Museum of Illusions Entrance Ticket

Pittsburgh: Museum of Illusions Entrance Ticket

£22
per adult
80% 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
Make new friends as you learn the exciting history of whiskey in Pittsburgh

Whiskey Rebellion & Prohibition Tour

£37
per adult
Whiskey Rebellion & Prohibition Tour
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.