Oakland Holidays from £1,182

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Top Oakland Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Americas Best Value Inn Pittsburgh Airport

Americas Best Value Inn Pittsburgh Airport

2 out of 5
Price was £1,337, price is now £1,182 per person
£1,182
per person
22 Dec - 29 Dec
found 6 hours ago
Return direct flight included
London (LON) to Pittsburgh (PIT)
6.6/10 (1,006 reviews)

The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

2 out of 5
North Side
Price was £1,772, price is now £1,491 per person
£1,491
per person
22 Dec - 29 Dec
found 7 hours ago
Return direct flight included
London (LON) to Pittsburgh (PIT)
9.4/10 Exceptional! (2,465 reviews)

Stay Pittsburgh

Stay Pittsburgh

2 out of 5
Downtown Pittsburgh
Price was £1,647, price is now £1,387 per person
£1,387
per person
22 Dec - 29 Dec
found 7 hours ago
Return direct flight included
London (LON) to Pittsburgh (PIT)
8/10 Very good! (339 reviews)

Fairmont Pittsburgh

Fairmont Pittsburgh

4.5 out of 5
Downtown Pittsburgh
Price was £2,064, price is now £1,814 per person
£1,814
per person
22 Dec - 29 Dec
found 7 hours ago
Return direct flight included
London (LON) to Pittsburgh (PIT)
8.8/10 Excellent! (1,004 reviews)
Great Stay for Our Anniversary Weekend We stayed at the Fairmont Pittsburgh for our wedding anniversary and had a great experience. We mentioned our anniversary when booking and were pleasantly surprised to find champagne and chocolates waiting in our room. A really thoughtful touch! The room and bathroom were both spacious, clean, and comfortable. Floor 2 also has a great bar with a nice atmosphere. Overall, a wonderful stay and a great place to celebrate a special occasion. We’d definitely stay again!

Reviewed on 1 Nov 2026

Kimpton Hotel Monaco Pittsburgh by IHG

Kimpton Hotel Monaco Pittsburgh by IHG

4.5 out of 5
Downtown Pittsburgh
Price was £1,782, price is now £1,583 per person
£1,583
per person
22 Dec - 29 Dec
found 7 hours ago
Return direct flight included
London (LON) to Pittsburgh (PIT)
9.4/10 Exceptional! (1,324 reviews)
Amazing experience

Reviewed on 1 Nov 2026

Oakland Essential Information

Language
English
Currency
U.S dollars
Population
1,550
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
McConnells Mill State Park, Living Treasures Wild Animal Park and Knockin Noggin Cidery & Winery

Top hotels in Oakland

Holiday Inn Youngstown South by IHG

Holiday Inn Youngstown South by IHG

3 out of 5
7410 South Ave Boardman OH
Fully refundable
The price is £78 per night from 29 Nov to 30 Nov
£78
29 Nov - 30 Nov
includes taxes & fees
8.4/10 Very good! (818 reviews)
"Would stay again"

Reviewed on 30 Oct 2026

Holiday Inn Youngstown South by IHG
Comfort Suites Youngstown North

Comfort Suites Youngstown North

2.5 out of 5
201 Perni Ln Youngstown OH
Fully refundable
The price is £79 per night from 22 Nov to 23 Nov
£79
22 Nov - 23 Nov
includes taxes & fees
Comfort Suites Youngstown North
Wingate by Wyndham Grove City

Wingate by Wyndham Grove City

3 out of 5
118 Garrett Dr Grove City PA
Fully refundableReserve now, pay when you stay
The price is £75 per night from 15 Nov to 16 Nov
£75
15 Nov - 16 Nov
includes taxes & fees
Wingate by Wyndham Grove City
See all 254 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?
Tailor make your Oakland travel package from only £1,182. Choose from any combination of hotels, flights and rental cars to craft the trip you've long been dreaming about. Remember to add on one or two experiences!
If I'm not able to travel, can I cancel my Oakland travel package?
It's good to know that you can cancel your Oakland booking if your travel plans have changed. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. You may be able to change or cancel your booking for free if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.
How do I get a cheap travel package to Oakland?
If you love landing a bargain, combine your bookings into an Oakland travel package. Whether you're searching for hotels, flights, rental cars or day tours, you can book them all in one place. You'll have loads of choice at your fingertips too. Expedia has more than 550 airlines and 1,000,000 hotel options globally to select from. Fly with who you prefer, stay wherever you like and save some cash — now that's the ideal holiday!
Does Expedia offer Book Now, Pay Later Oakland holidays?
We certainly do. Expedia has joined forces with online lender Klarna to help you easily pay for your trip in instalments. Simply choose the payment plan that suits best during the checkout process and take away the stress of budgeting for your trip. Remember to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your holiday buck. Browse our flexible payment options below:

  • Pay monthly holidays: If paying small amounts each month sounds right for you, Klarna can help. Paying in convenient monthly instalments will make that dream getaway possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay off your holiday across multiple transactions.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan with Klarna.

Where should I stay in Oakland?
With loads to explore in Oakland, we suggest you book a room in a hotel close to its attractions. New Castle Primary Care, UPMC Jameson and Hospital Butler Memorial are some good ones to put on your must-see list.
What are the top hotels in Oakland?
If this will be your first time in Oakland, book a room at Club Quarters Hotel Rittenhouse Square, Philadelphia or Mount Airy Casino and Resort. Both hotels offer friendly service and are popular options with many travellers.
How far in advance should I book my Oakland holiday?
While not all air carriers advertise tickets early, you can normally look up international airfares on Expedia up to 12 months in advance. This is when you'll nab some incredible deals. If you've left everything to the last minute, you could still be in luck. Low prices sometimes appear just weeks before departure.
What does an Expedia Oakland travel package include?
Hotels, flights and a cool car for all your fun road trip adventures. Simply select your preferred bundle and gain access to great discounts. Once you've made your booking, add on a couple of sightseeing tours and watch your savings pile up. When it comes to organising your Oakland holiday, you're in charge!
What should I know before booking an Oakland travel package?
A package can be easier on the hip pocket than separately booking everything you need for your escape. For example, bundle your hotels, flights and rental cars and save a pretty penny. Whatever your holiday goals are, you'll find a package that's perfect for you.
Can I choose my airline with an Oakland Expedia travel package?
Expedia offers access to more than 550 airline partners worldwide, so you definitely can. Just select your preferred air carrier and put together the perfect Oakland getaway.

* 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.