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
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in Oakland

Rice Hill Inn
Rice Hill Inn
2 out of 5
621 John Long Rd, Oakland, OR
Fully refundableReserve now, pay when you stay
The price is S$111 per night from 7 Dec to 8 Dec
S$111
includes taxes & fees
7 Dec - 8 Dec
7.4/10 Good! (190 reviews)
"Basic but good for the price...a new Indian food truck just opened outside and it was amazing with other food options being the truck stop (have to walk along the main road to get there)"

Reviewed on 18 Oct,2024

Rice Hill Inn
The Ranch Motel
The Ranch Motel
2 out of 5
581 John Long Rd, Oakland, OR
9/10 Wonderful! (54 reviews)
"Although it is of course a bit dated, the staff is friendly and accommodating. Overall a pleasant stay."

Reviewed on 28 Nov,2023

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The Ranch Motel
Riverfront Inn Roseburg
Riverfront Inn Roseburg
2 out of 5
315 W Harvard Ave, Roseburg, OR
Fully refundableReserve now, pay when you stay
The price is S$145 per night from 1 Dec to 2 Dec
S$145
includes taxes & fees
1 Dec - 2 Dec
8.4/10 Very Good! (1,223 reviews)
"Stayed here many times, great cozy hotel on the river."

Reviewed on 21 Nov,2024

Riverfront Inn Roseburg
See all 110 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?
From just . Yes, you read that correctly. Our Oakland holiday packages are a great way to make your budget last longer. Combine your preferred flights, hotels and rental car and get out and explore this lively destination.
How do I get a cheap travel package to Oakland?
Find flights that suit your schedule, add a hotel room to your booking and watch the savings rack up with an Oakland holiday package. It’s as easy as that! From hotels and flights to tours and rental cars, Expedia is where your cheap getaway begins. And with over 550 airlines and 1,000,000 hotels worldwide to pick from, you won’t be short of choice.
Where should I stay in Oakland?
A getaway to Oakland wouldn’t be complete without checking out Misty Oaks Vineyard, MarshAnne Landing and Oakland City Park. Spend your evenings close to these top attractions and make sightseeing easy.
How far in advance should I book my Oakland holiday?
Reserving your tickets early with Expedia means one less thing to worry about. A number of air carriers display prices up to a year in advance. This is usually the cheapest time to book. If circumstances have left you booking late, discount flights to Oakland sometimes emerge just weeks before departure.
What does an Expedia Oakland travel package include?
Flights, hotels and a cool car for all your road trip adventures. Simply pick and choose your preferred bundle and get access to great discounts. Once you’ve made your booking, add on a few tours and activities and watch your savings pile up. When it comes to creating your Oakland holiday, you’re in charge!
What should I know before booking an Oakland travel package?
Discover deals that suit your budget with an Expedia package. Flights, hotels, rental cars — we’ve got everything you need to plan your getaway. You’ll save big bucks just by combining your bookings. Whether you’re heading away on a snow and ski adventure or sunning yourself on a warm beach, your ideal holiday is just a few clicks away.
Can I choose my airline with an Oakland Expedia holiday package?
Yes, and with over 550 airlines to pick from around the world, you’re not short on choice. Have a look through the available options and see which airline best fits your needs and budget.
If I'm not able to travel, can I cancel my Oakland holiday package?
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 cancel or change free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.

* 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.