Oakland Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 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 hotels in Oakland
Rice Hill Inn
621 John Long Rd Oakland OR
Fully refundableReserve now, pay when you stay
S$92
10 Aug - 11 Aug
includes taxes & fees
8/10 Very good! (297 reviews)
"Convenient location for me, quiet, and the staff have always been friendly."
Reviewed on 4 Aug, 2026
The Ranch Motel
581 John Long Rd Oakland OR
S$119
15 Aug - 16 Aug
includes taxes & fees
9.2/10 Wonderful! (139 reviews)
"Unique, clean and friendly motel. Love the drive right up to the front door for easy loading and unloading. This is our 2nd stay here and we will choose it again when traveling through the West Coast on I-5."
Reviewed on 2 Aug, 2026
Southern Oregon Cabin: Fire Pit & Private Pond!
Oakland OR
10/10 Exceptional! (1 review)
"Cute little place! Especially liked the patio and outside areas. Inside needs a few finishing touches like coat hooks on back of doors, but place is very new, clean and worked great for our few days there."
Reviewed on 25 Oct, 2024
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.
Stay near popular Oakland attractions
MarshAnne Landing
5.0/10 (6 reviews)
You can enjoy a tasting or tour at MarshAnne Landing during your travels to Oakland. While in this family-friendly area, you can savour the top-notch restaurants.
Oakland City Park
6.8/10 (16 reviews)
Oakland City Park is just one of the places to see in Oakland, so why not enjoy the other things to explore during your travels? While in this trendy area, you can savour the top-notch restaurants.
Frequently asked questions
How much does an Oakland holiday package cost?
You can pick up a holiday package to this destination on Expedia. However, how much your holiday to Oakland costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Oakland?
You can typically find lower rates and greater availability in February, May and August. Browse our cheap Oakland holiday packages and you could get some excellent off-season deals.
How many days is enough for Oakland?
Typically, a handful of days is enough to check out the top sights during your Oakland holiday. But if you'd like to have some time to relax or take day trips, consider extending your itinerary.
How to find the best Oakland package deals?
Use Expedia's filter tool to help you find some of the best Oakland package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Oakland package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your holiday package as early as possible.
Is it cheaper to book an Oakland holiday as a package?
An Expedia holiday package could land you great savings when compared to booking flights and stays separately. Better still, you can customise your Oakland escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Oakland?
If you've got your Oakland holiday dates finalized, book as soon as you can to bag some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for quick escapes.
How to plan a trip to Oakland?
- Choose your dates: What you'd like to do in Oakland and your favourite season will help you decide when to travel.
- Plan your budget wisely: Besides the cost of your hotel, you'll need to consider other expenses too. These include flights, food and transportation. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Oakland.
- Determine how many days away: Start by compiling a list of the activities and attractions you want to experience in Oakland. Then, estimate how long you'll need for each, as well as any travel time.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick 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.
