Oakland Holidays from £799

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Your Oakland Holiday

From its cycling to its walking, there's tons to like about Oakland. Book a customized Oakland holiday package and get set to experience the wonders of this neighbourhood. Your trip to Oakland wouldn't be complete without stopping by popular attractions nearby such as PNC Park, Acrisure Stadium and University of Pittsburgh. Expedia will help put your travel plans into action. Book your perfect Oakland holiday today.

Price found within the past 48 hours. Click for updated prices.
Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was £977, price is now £799 per person
£799
per person
10 Oct - 13 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Pittsburgh (PIT)
7.8/10 Good! (169 reviews)
Only a couple of visible stains, nothing out of the ordinary. Very convenient hotel booking with affordable rates. Support was very responsive to questions. Would absolutely stay again.

Reviewed on 26 Aug 2025

Placemakr Downtown Pittsburgh at The Pennsylvanian

Placemakr Downtown Pittsburgh at The Pennsylvanian

4 out of 5
Downtown Pittsburgh
Price was £1,398, price is now £1,055 per person
£1,055
per person
10 Oct - 13 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Pittsburgh (PIT)
7.6/10 Good! (16 reviews)
Unique, incredible preservation of the historical aspects of the property fused with modern design in the condos .

Reviewed on 25 Aug 2025

Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
Downtown Pittsburgh
Price was £1,560, price is now £1,215 per person
£1,215
per person
10 Oct - 13 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Pittsburgh (PIT)
8.8/10 Excellent! (1,000 reviews)
Everything was great

Reviewed on 12 Aug 2025

The Westin Pittsburgh, a Marriott Hotel

The Westin Pittsburgh, a Marriott Hotel

4 out of 5
Downtown Pittsburgh
Price was £1,108, price is now £889 per person
£889
per person
10 Oct - 13 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Pittsburgh (PIT)
8.6/10 Excellent! (1,001 reviews)
The property was great the and the sfaff were awesome.

Reviewed on 17 Aug 2025

Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG

4.5 out of 5
Downtown Pittsburgh
Price was £1,411, price is now £1,161 per person
£1,161
per person
10 Oct - 13 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Pittsburgh (PIT)
9.4/10 Exceptional! (1,212 reviews)
One of my favorites! Always clean and comfortable Great bar/restaurant.

Reviewed on 24 Aug 2025

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
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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 Oakland

Courtyard by Marriott Pittsburgh University Center

Courtyard by Marriott Pittsburgh University Center

3.5 out of 5
100 Lytton Avenue, Pittsburgh, PA
The price is £110 per night from 28 Aug to 29 Aug
£110
28 Aug - 29 Aug
includes taxes & fees
8.8/10 Excellent! (415 reviews)
"excellent"

Reviewed on 23 Aug 2025

Courtyard by Marriott Pittsburgh University Center
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 £101 per night from 1 Sept to 2 Sept
£101
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Perfect place to stay - uplifting staff"

Reviewed on 23 Aug 2025

Hotel Indigo Pittsburgh University-Oakland by IHG
The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection

4.5 out of 5
5130 Bigelow Boulevard, Pittsburgh, PA
The price is £159 per night from 28 Aug to 29 Aug
£159
28 Aug - 29 Aug
includes taxes & fees
9.2/10 Wonderful! (678 reviews)
"close to all"

Reviewed on 23 Aug 2025

The Oaklander Hotel, Autograph Collection
See all 1,779 properties in 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 an Oakland travel package cost?
From as little as £799, you can tailor your Oakland package the way you want. Simply combine hotels, flights and car rentals and we'll reward you with discounts.
If I'm not able to travel, can I cancel my Oakland travel package?
Yes, you can. We get that life doesn't always go to plan, so we're here to help if you need to make changes to your Oakland travel package. You may be able to change or cancel your itinerary at no cost if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if your booking was made more than 24 hours ago. Have a look at our Customer Service Portal for further information. Also, check your itinerary for the nitty-gritty on change fees.
How do I get a cheap travel package to Oakland?
Booking an Oakland travel package with Expedia is one of the easiest ways to save. We offer more than 550 air carriers and 1,000,000 properties around the world. With such a broad range to choose from, you'll have no worries pulling together your dream holiday.
Does Expedia offer Book Now, Pay Later Oakland holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has come up with a solution to help. Now that we've formed a partnership with online lender Klarna, it's easier than ever to book a fabulous getaway without draining your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your trip. Consider one of these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's easy monthly instalment plans. If paying small amounts each month sounds right for you, pick this option during the checkout process.
  • Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Then go for this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: Pressing the "book now" button is much easier with this payment plan. Just put down a small deposit on your booking and then get on your way.

Where should I stay in Oakland?
A visit to Oakland isn't complete without stopping by Acrisure Stadium and University of Pittsburgh. Look for somewhere to stay close by so you can easily access these terrific tourist attractions.
What are the top hotels in Oakland?
Secure a room at Hyatt Regency Pittsburgh International Airport. It's one of this area's most sought-after properties. Another top-rated option in Oakland is Doubletree by Hilton Pittsburgh Greentree.
How far in advance should I book my Oakland holiday?
To land rock-bottom prices, book as early as you can. Airlines typically release flight tickets, along with some of the lowest fares, around 12 months ahead of time. Hotels, car rental and activities should also be booked well in advance to avoid disappointment. If you're in need of a last-minute getaway in Oakland, there are always lots of great deals on Expedia. Book something in today!
What does an Expedia Oakland travel package include?
Hotels, flights and rental cars — you'll find them all here. With Expedia, you can create your Oakland travel package your way. All you have to do is work out what you need. Once you've made your booking, you can add on fun things like tours and activities. The more you bundle, the bigger the savings!
What should I know before booking an Oakland travel package?
You can save big by combining your flights, hotels and rental cars. Once you've made your booking, you can add on sightseeing tours or experiences. Your next unforgettable adventure is only a couple of clicks away.
Can I choose my airline with an Oakland Expedia travel package?
Yes, you're in charge. We offer more than 550 partner airlines across the globe, so you can design your Oakland trip according to your budget and travel needs.

Popular places to visit

University of Pittsburgh

University of Pittsburgh

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

Things to do

Pittsburgh, PA: Sandcastle Waterpark Entry Ticket

Pittsburgh, PA: Sandcastle Waterpark Entry Ticket

£23
per adult
Pittsburgh, PA: Sandcastle Waterpark Entry Ticket
Visit beautiful shopping and dining complex in your private tour

Private City Kickstart Tour: Tokyo

£100
per adult
100% of travellers recommend
Private City Kickstart Tour: Tokyo
Pittsburgh Pirates Baseball Game at PNC Park

Pittsburgh Pirates Baseball Game at PNC Park

£41
per adult
Pittsburgh Pirates Baseball Game at PNC Park
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.