Oakland Holidays

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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.

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh which includes a bridge and a river or creek

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 Benedum Center or Heinz Hall 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
Fully refundableReserve now, pay when you stay
The price is £95 per night from 23 Feb to 24 Feb
£95
23 Feb - 24 Feb
includes taxes & fees
9/10 Wonderful! (600 reviews)
Room was clean and beautiful. Nice walk in shower. Staff was very friendly and helpful.

Reviewed on 5 Feb 2026

Courtyard by Marriott Pittsburgh University Center
The Oaklander Hotel, Autograph Collection

The Oaklander Hotel, Autograph Collection

4.5 out of 5
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
The price is £163 per night from 18 Feb to 19 Feb
£163
18 Feb - 19 Feb
includes taxes & fees
9.2/10 Wonderful! (741 reviews)
Friendly folks at the front desk. Kayla the bartender was awesome! The room was stocked with top notch products and amenities. Wish we could have stayed one more night, as it was so comfortable and welcoming.

Reviewed on 2 Feb 2026

The Oaklander Hotel, Autograph Collection
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 £99 per night from 17 Feb to 18 Feb
£99
17 Feb - 18 Feb
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
Cool atmosphere, spotless rooms, and friendly staff for a great price!

Reviewed on 1 Feb 2026

Hotel Indigo Pittsburgh University-Oakland by IHG
See all 1,936 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 , 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 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

Things to do

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
Smartphone-Guided Tour of Downtown Pittsburgh Sights & Stories

Smartphone-Guided Tour of Downtown Pittsburgh Sights & Stories

£20
per traveller
Smartphone-Guided Tour of Downtown Pittsburgh Sights & Stories
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.