Oakland Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Oakland flight + hotel deals
- Radio Hotel
10 Sept - 14 SeptRadio Hotel + Flight
Manhattan4 nights4.0 star property8.6/10 - Excellent (2,482 reviews)"My comforter was stained and so was the window shade. The shower faucet was broken. An item was stolen from my room and when I reported it to the manager, he told me it was “Not his problem”"Reviewed July 17, 2026Return • Shannon (SNN) - New York (JFK)SNN - JFK • Direct JFK - SNN • Direct - Hotel Riu Plaza New York Times Square
1 Sept - 6 SeptHotel Riu Plaza New York Times Square + Flight
Manhattan5 nights4.0 star property9.0/10 - Wonderful (3,205 reviews)"The morning buffet was not good , the food was subpar ?.. nothing extraordinary, I felt like I was being herded into an area to eat in a manufacturing factory .."Reviewed July 16, 2026Return • Dublin (DUB) - New York (JFK)DUB - JFK • Direct JFK - DUB • Direct - Hotel Riu Plaza Manhattan Times Square
1 Sept - 6 SeptHotel Riu Plaza Manhattan Times Square + Flight
Manhattan5 nights4.0 star property9.2/10 - Wonderful (3,747 reviews)"There were issues with the elevators. Every time they stopped on our floor they were completely full. After waiting for 20 minutes we finally took the elevator going up just so we can go down."Reviewed July 17, 2026Return • Dublin (DUB) - New York (JFK)DUB - JFK • Direct JFK - DUB • Direct - Roxy Hotel New York
20 Sept - 26 SeptRoxy Hotel New York + Flight
Manhattan6 nights4.5 star property9.4/10 - Exceptional (1,600 reviews)"Beautiful hotel, incredible staff and service. Entertainment at Roxy was fabulous!"Reviewed July 16, 2026Return • Dublin (DUB) - New York (JFK)DUB - JFK • Direct EWR - DUB • Direct - Hotel St. James
1 Sept - 6 SeptHotel St. James + Flight
Manhattan5 nights3.0 star property8.8/10 - Excellent (7,613 reviews)"All was very good, the staff is very kind, they are all always aware of the safety of the place. The location is amazing."Reviewed July 17, 2026Return • Dublin (DUB) - New York (JFK)DUB - JFK • Direct JFK - DUB • Direct
Frequently Asked Questions
How much does an Oakland holiday package cost?
You'll find cheap prices from €796 on Expedia for your Oakland escape. However, factors like the season, choice of hotel and length of stay will influence how much your holiday to Oakland costs.
What are the cheapest months to go to Oakland?
If you're looking to snag a cheap Oakland holiday package, consider travelling in January, February and March. You're likely to find lower rates on accommodation and flights during these months — perfect for travellers wishing to save money.
How many days is enough for Oakland?
The ideal duration for your Oakland holiday depends on what you'd like to do. Typically, a handful of days to a week will give you plenty of time to hit all the main attractions and explore some hidden spots along the way.
How to find the best Oakland package deals?
Begin your search for an Oakland package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Oakland package deal right away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Oakland adventure off to a flying start.
Is it cheaper to book an Oakland holiday as a package?
You can enjoy significant savings on your next Oakland getaway by booking a personalised holiday package. Check the "Package" heading, then select your destination and travel dates to see the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Oakland?
Score incredible discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Oakland adventure.
How to plan a trip to Oakland?
- Pick your dates: The things you plan to do in Oakland and your favourite season will help you decide when to go.
- Work out your budget: Make sure you have enough money to cover everything from food and transportation to activities and flights. Your hotel will likely be the largest expense during your trip to Oakland.
- Decide your trip length: Consider how long you want to spend exploring Oakland. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
- Combine your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to choose an Oakland holiday package that brings all your bookings together.