Oakland Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Oakland

Park Inn by Radisson Sharon
Park Inn by Radisson Sharon
3.5 out of 5
3377 New Castle Road, West Middlesex, PA
Fully refundable
The price is S$83 per night from 15 Jun to 16 Jun
S$83
15 Jun - 16 Jun
includes taxes & fees
6.6/10 (1,004 reviews)
"Needs updating a lil new owners looks to be starting a remodel so have high hopes in the future"

Reviewed on 9 Jun, 2025

Park Inn by Radisson Sharon
Baymont by Wyndham Boardman
Baymont by Wyndham Boardman
2.5 out of 5
7393 South Ave, Boardman, OH
Fully refundableReserve now, pay when you stay
The price is S$96 per night from 15 Jun to 16 Jun
S$96
15 Jun - 16 Jun
includes taxes & fees
5.6/10 (762 reviews)
"Good for the price"

Reviewed on 6 Jun, 2025

Baymont by Wyndham Boardman
Wingate by Wyndham Grove City
Wingate by Wyndham Grove City
2.5 out of 5
118 Garrett Dr, Grove City, PA
Fully refundableReserve now, pay when you stay
The price is S$121 per night from 15 Jun to 16 Jun
S$121
15 Jun - 16 Jun
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Outside of the building was being painted and when we drove up to it I was a little worried but it was actually very nice inside. I stayed in 5 different hotels last week and the wingate had the most comfortable bed by far"

Reviewed on 8 Jun, 2025

Wingate by Wyndham Grove City
See all 219 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.

Frequently asked questions

How much does an Oakland holiday package cost?
Offering great value package deals on Expedia, you’ll be pleasantly surprised at how much a holiday to Oakland costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Oakland?
If you’re looking to score a cheap Oakland holiday package, consider planning a trip in January, February and March. You’ll generally find lower prices on airfares and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for Oakland?
The ideal duration for your Oakland holiday depends on what you’d like to see. Generally, a handful of days to a week will give you time to tick off all the top attractions and discover some hidden treasures along the way.
How to find the best Oakland package deals?
Use Expedia’s handy filters to find some of the best Oakland package deals. When you begin your search, simply set your maximum budget and then order the results by “Price: low to high.” If you want to save, plan your escape for midweek, or browse for Oakland package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it’s typically best to lock in your holiday package well in advance.
Is it cheaper to book an Oakland holiday as a package?
An Expedia holiday package could land you significant savings when compared to booking stays and flights separately. Better still, you can customise your Oakland trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Oakland?
Land incredible discounts by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Oakland break.
How to plan a trip to Oakland?

  1. Pick your travel dates: The things you want to do in Oakland and your preferred season can help you decide when to go.
  2. Plan your budget wisely: Besides the cost of your stay, you should consider other expenses. These include flights, food and transportation. Also, put aside some extra funds for unexpected expenses that could arise during your trip to Oakland.
  3. Decide your trip length: Consider how long you’d like to spend exploring Oakland. Plan your itinerary so you can get to all the attractions and activities you’re interested in at a leisurely pace.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that’s left is to choose an Oakland holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.