Oakland Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Marc Maheu

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Oakland Holiday

Our pick of the best Oakland Hotel Deals

Rustic Farm Retreat with Pool and Farm animals -Family & Pet Friendly!
Rustic Farm Retreat with Pool and Farm animals -Family & Pet Friendly!
Oakland
10/10 Exceptional! (1 review)
A great 1st exerience with Vrbo
"The property we rented was as advertised - 3 bedrooms and a 10-minute drive from Colby College, where we attended our college reunion. The house was older but had modern appliances, 2 bathrooms, a washer and dryer. The home is on a farm with horses and a mule on the premises, which we enjoyed. The ..."

Reviewed on 22 Jun. 2025

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Rustic Farm Retreat with Pool and Farm animals -Family & Pet Friendly!
Sister A-Frame in Woods B
Sister A-Frame in Woods B
Oakland
The price is NZ$384 per night from 30 June to 1 July
NZ$384
30 June - 1 July
includes taxes & fees
10/10 Exceptional! (1 review)
Cute place tucked in the woods
"Great stay. Would stay here again if in the area."

Reviewed on 4 Jun. 2025

Sister A-Frame in Woods B
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Oakland
9.4/10 Exceptional! (52 reviews)
"Had a very peacefully stay. Was a very nice weekend getaway during cancer treatments. Fishing and sitting by the water was soothing."

Reviewed on 18 Jun. 2025

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Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
See all 532 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?
You'll find cheap prices on Expedia for your Oakland break. However, factors like the length of stay, hotel choice and season will influence how much your holiday to Oakland costs.
What are the cheapest months to go to Oakland?
To score cheap Oakland holiday packages, plan your trip outside of peak periods such as public holidays. You'll generally find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Oakland?
Generally, a handful of days is enough to visit the major sights during your Oakland holiday. However, if you prefer to have time to rest or take day trips, consider extending your trip.
How to find the best Oakland package deals?
Start your search for an Oakland package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Oakland package deal straight away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oakland escape underway.
Is it cheaper to book an Oakland holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Oakland holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Oakland?
If you have your Oakland holiday dates finalized, book as soon as you can to grab some awesome deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Oakland?

  1. Choose when to go: Check your calendar and get your bags packed. Your favourite season and the type of activities available will also help you decide when to visit Oakland.
  2. Set a budget: Consider costs such as flights, meals and transportation when working out how much to put aside for your trip to Oakland. Then, pick a property that fits your budget, whether that's an economical option or a deluxe retreat.
  3. Set the duration of your trip: Start by making a list of all the attractions and activities you'd like to experience in Oakland. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Oakland holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.