Oakland Vacations

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Find the Best Oakland Vacation Packages

Oakland Hotel Deals

Days Inn & Suites by Wyndham Bowling Green

Days Inn & Suites by Wyndham Bowling Green

2 out of 5
181 Cumberland Trace Rd, Bowling Green, KY
Fully refundableReserve now, pay when you stay
The price is ₩81,404 per night from Aug 28 to Aug 29
₩81,404
₩92,328 total
Aug 28 - Aug 29
includes taxes & fees
8/10 Very Good! (1,298 reviews)
Great hotel!!
"Stated for 2 nights and the room was quiet and clean and close to everything we needed in town. Would definitely stay again!!!"

Reviewed on Aug 8, 2025

Days Inn & Suites by Wyndham Bowling Green
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 ₩81,390 per night from Sep 1 to Sep 2
₩81,390
₩90,588 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (1,006 reviews)
"The rooms just need upgrades the Gentleman at the front desk was very nice and helpful and the check-in was fast"

Reviewed on Aug 10, 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 ₩144,718 per night from Aug 17 to Aug 18
₩144,718
₩159,538 total
Aug 17 - Aug 18
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
"Excellent location. Excellent value. Close to where we needed to be."

Reviewed on Jul 31, 2025

Holiday Inn Express Horse Cave by IHG
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.