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.

Price found within the past 48 hours. Click for updated prices.
  • Terrace/patio
    Aug 30 - Aug 31

    Joinery Hotel Pittsburgh, Curio Collection by Hilton + Flight

    Downtown Pittsburgh
    1 night
    4.0 star property
    8.6/10 - Excellent (1,527 reviews)
    "I havnt slept that good in a while , right when I woke up I lifted the sheets to see what brand mattress and pillows they were. 100 out of 10"
    Reviewed June 5, 2026
    Return • Boston (BOS) - Pittsburgh (PIT)
    BOS - PIT • Direct PIT - BOS • Direct
    £259
    £242
    per traveller
    found 15 hours ago
    Joinery Hotel Pittsburgh, Curio Collection by Hilton
  • Living area
    Aug 30 - Aug 31

    Traveler's Rest Hotel + Flight

    South Side Flats
    1 night
    2.0 star property
    9.6/10 - Exceptional (102 reviews)
    "Perfect stay! The attention to detail, full fridge , friendly host , great room. This made our stay in Pittsburgh a special one . Thank you !"
    Reviewed May 27, 2026
    Return • Boston (BOS) - Pittsburgh (PIT)
    BOS - PIT • Direct PIT - BOS • Direct
    £282
    £261
    per traveller
    found 15 hours ago
    Traveler's Rest Hotel
  • Exterior
    Aug 30 - Aug 31

    Hilton Garden Inn Pittsburgh University Place + Flight

    Central Oakland
    1 night
    3.0 star property
    8.8/10 - Excellent (1,002 reviews)
    "All good"
    Reviewed June 3, 2026
    Return • Boston (BOS) - Pittsburgh (PIT)
    BOS - PIT • Direct PIT - BOS • Direct
    £279
    £258
    per traveller
    found 15 hours ago
    Hilton Garden Inn Pittsburgh University Place
  • Property amenity
    Aug 30 - Aug 31

    The Oaklander Hotel, Autograph Collection + Flight

    Oakland
    1 night
    4.5 star property
    9.2/10 - Wonderful (781 reviews)
    "Great!!! John, the concierge was incredible!!! Thanks"
    Reviewed June 1, 2026
    Return • Boston (BOS) - Pittsburgh (PIT)
    BOS - PIT • Direct PIT - BOS • Direct
    £289
    £268
    per traveller
    found 15 hours ago
    The Oaklander Hotel, Autograph Collection
  • Restaurant
    Aug 30 - Aug 31

    Sheraton Pittsburgh Hotel at Station Square + Flight

    South Shore
    1 night
    3.5 star property
    9.0/10 - Wonderful (1,090 reviews)
    "Spacious room with modern decor, comfortable beds and spectacular view of the city, river and boats. We had breakfast at the Factory and it was excellent. The portions were huge, the food was delicious and the server was outstanding. Front desk staff was friendly and very knowledgeable about the surrounding area. Lots to do within walking distance and the walk along the river was fantastic. We stayed there a few years ago and it was a significantly better experience this time around. They have a..."
    Reviewed June 1, 2026
    Return • Boston (BOS) - Pittsburgh (PIT)
    BOS - PIT • Direct PIT - BOS • Direct
    £272
    £254
    per traveller
    found 15 hours ago
    Sheraton Pittsburgh Hotel at Station Square

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

3 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 £108 per night from 14 Jun to 15 Jun
£108
14 Jun - 15 Jun
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"The front desk lady wasn’t very nice whenever I told her I didn’t have the room type I booked. She was very odd and asked me for my email randomly and still signed me up for membership. I didn’t ask for she did switch my room but just wasn’t really nice about it. She had glasses"

Reviewed on 4 Jun 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 £127 per night from 30 Jun to 1 Jul
£127
30 Jun - 1 Jul
includes taxes & fees
8.2/10 Very Good! (3,576 reviews)
"very nice hotel. there are extra fees for parking."

Reviewed on 3 Jun 2026

Wyndham Grand Pittsburgh Downtown
The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
757 Casino Dr Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is £122 per night from 14 Jun to 15 Jun
£122
14 Jun - 15 Jun
includes taxes & fees
9.4/10 Exceptional! (1,787 reviews)
"Great"

Reviewed on 4 Jun 2026

The Landing Hotel at Rivers Casino
See all 2,038 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

5/5(1 review)

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

University of Pittsburgh
PPG Paints Arena

PPG Paints Arena

5/5(2 reviews)

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

£21
per adult
80% of travellers recommend
Pittsburgh: Museum of Illusions Entrance Ticket
This tour is the best tour for sports fans! Big fun guaranteed!

New! Black & Gold Sports History Tour for Sports Fans

£25
per adult
New! Black & Gold Sports History Tour for Sports Fans
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
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.