Oakland Holidays

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    Better together

    Save up to €185 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

Top Flight + Hotel Deals in Oakland

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Nashville Green Hills
Bobby Hotel
1 Hotel Nashville
Margaritaville Hotel Nashville
Placemakr Premier SoBro

Top hotels in Oakland

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 €64 per night from 3 Aug to 4 Aug
€64
3 Aug - 4 Aug
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"Upon check in the staff was very friendly! Our room was on the ground level! It was 96 degrees outside and our room was a cool 70! Room was very clean, bathroom was cleaner than some 5 star hotels! I was a little worried as all of the rooms are outside entrance but no problems whatsoever!! We would ..."

Reviewed on 29 Jul 2025

Red Roof Inn & Suites Cave City
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 €107 per night from 13 Aug to 14 Aug
€107
13 Aug - 14 Aug
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"This hotel is literally right off of the highway (65) so very convenient. Breakfast was good. They even had a pork-free sausage option which was amazing for our family. A few spiders near/under the AC unit (since we had to unplug and plug it). AC does kick on and off throughout the night instead ..."

Reviewed on 30 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 €68 per night from 10 Aug to 11 Aug
€68
10 Aug - 11 Aug
includes taxes & fees
8.2/10 Very Good! (299 reviews)
Good stop!
"The room was very comfortable and extremely clean. The only complaint I has is there is not a blackout curtain. Otherwise, it’s an excellent and very reasonable place to stay when traveling."

Reviewed on 25 Jul 2025

Woodspring Suites Bowling Green I-65
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 from €789 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.