Oakland Trips (flight + hotel)

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    Save up to P 3,118 when you book a flight and hotel together*
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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 P3,743 per night from Jul 28 to Jul 29
P3,743
P4,166 total
Jul 28 - Jul 29
includes taxes & fees
8.4/10 Very Good! (1,010 reviews)
"Not their fault, but had to run AC constantly to keep floor from getting wet."

Reviewed on Jul 23, 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 P5,973 per night from Aug 24 to Aug 25
P5,973
P6,585 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"Every thing was great"

Reviewed on Jul 24, 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 P3,925 per night from Jul 27 to Jul 28
P3,925
P4,452 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very Good! (295 reviews)
"Good room for the price"

Reviewed on Jul 18, 2025

Woodspring Suites Bowling Green I-65
See all 457 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 vacation 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 vacation 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 vacation 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 vacation. 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 vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays separately. Better still, you can customize 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 vacation 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 favorite 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 vacation 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.