Oakland Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by L Ru

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 2.127.931 ₫ per night from 17 Aug to 18 Aug
2.127.931 ₫
2.159.723 ₫ total
17 Aug - 18 Aug
includes taxes & fees
7.6/10 Good! (214 reviews)
Great little budget hotel
"Check in was fast, front desk gal was friendly, room was clean, AC worked. Quick stop while traveling and it stored our needs and was a great price. Beds are not the most comfortable but it was adequate for what we paid. I felt safe as a woman traveling alone with kids"

Reviewed on 7 Aug 2025

Rice Hill Inn
The Ranch Motel

The Ranch Motel

2 out of 5
581 John Long Rd, Oakland, OR
8.8/10 Excellent! (79 reviews)
A cool place to stay
"The lady at the front desk was very nice. A unique place to stay, clean room, and easy parking."

Reviewed on 7 Aug 2025

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The Ranch Motel
Southern Oregon Cabin: Fire Pit & Private Pond!

Southern Oregon Cabin: Fire Pit & Private Pond!

3 out of 5
Oakland, OR
"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

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Southern Oregon Cabin: Fire Pit & Private Pond!
See all 131 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.

Popular places to visit

Misty Oaks Vineyard

You can enjoy a tasting or tour at Misty Oaks Vineyard during your travels to Oakland. While in this walkable area, you can savour the top-notch restaurants.

Misty Oaks Vineyard

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?

  1. Choose your dates: What you'd like to do in Oakland and your favourite season will help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.