Oakland Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to NZ$616 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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    Rest easy
    Plan, book, and manage your trip all in one place

Oakland Holiday

Our pick of the best Oakland Hotel Deals

Holiday Inn Express Horse Cave by IHG
Holiday Inn Express Horse Cave by IHG
2.5 out of 5
750 Flint Ridge Rd, Horse Cave, KY
Fully refundable
The price is NZ$204 per night from 11 July to 12 July
NZ$204
11 July - 12 July
includes taxes & fees
8.2/10 Very Good! (1,009 reviews)
"Overall good stay"

Reviewed on 5 Jul. 2025

Holiday Inn Express Horse Cave by IHG
Woodspring Suites Bowling Green I-65
Woodspring Suites Bowling Green I-65
2.5 out of 5
175 Orange Court, Bowling Green, KY
Fully refundableReserve now, pay when you stay
The price is NZ$129 per night from 13 July to 14 July
NZ$129
13 July - 14 July
includes taxes & fees
8.2/10 Very Good! (267 reviews)
Nice place
"Very clean and modern. Well maintained."

Reviewed on 5 Jul. 2025

Woodspring Suites Bowling Green I-65
Red Roof Inn & Suites Cave City
Red Roof Inn & Suites Cave City
2 out of 5
807 Mammoth Cave St, Cave City, KY
Fully refundableReserve now, pay when you stay
The price is NZ$117 per night from 13 July to 14 July
NZ$117
13 July - 14 July
includes taxes & fees
8.4/10 Very Good! (1,011 reviews)
"It’s clean and comfortable. The room was spacious. No amenities, but close to the little downtown area that has a good coffee shop. Easy drive to Mammoth Cave"

Reviewed on 6 Jul. 2025

Red Roof Inn & Suites Cave City
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 escape. However, a range of 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?
The off-season is the best time to travel to Oakland if you're hoping to keep costs down. Another tip for scoring cheap Oakland holiday packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Oakland?
Usually, a handful of days is enough to visit the main attractions during your Oakland holiday. But if you want to have more time to relax or take day trips, think about extending your trip.
How to find the best Oakland package deals?
Begin your search for an Oakland package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Oakland package deal straight away, just tweak 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?
An Expedia holiday package could land you considerable savings when compared to booking flights and stays 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 bundle deals and find out how much you can save.
When to book a holiday package to Oakland?
If you're planning a spur-of-the-moment Oakland adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Oakland?

  1. Choose your travel dates: What you plan to do in Oakland and your favourite season will help you decide when to travel.
  2. Set a budget: Consider expenses such as transportation, flights and meals when calculating how much to set aside for your trip to Oakland. Then, select a hotel that fits your budget, whether that's a wallet-friendly stay or a swankier getaway.
  3. Determine how many days away: Start by compiling a list of the activities and attractions you want to get to 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.

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