Oakland Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Oakland

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 S$86 per night from 18 Aug to 19 Aug
S$86
18 Aug - 19 Aug
includes taxes & fees
8/10 Very Good! (1,295 reviews)
Clean room and good greeting.
"I was greeted by a welcoming smile and taken care of right away. The room was clean and comfortable. Easy to feel comfortable. The property was clean and no issues with the parking lot. The only challenge I see is the breakfast. It was ho-hum. Very limited on the breakfast menu. I don’t know if it ..."

Reviewed on 12 Aug, 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 S$84 per night from 1 Sept to 2 Sept
S$84
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (1,009 reviews)
"Easy and quick check-in check out no issues"

Reviewed on 14 Aug, 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 S$143 per night from 15 Sept to 16 Sept
S$143
15 Sept - 16 Sept
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"We lived our room bed was comfortable Sheets soft. Loved the set up of the King with sofa bed. Loved the breakfast. The fresh ground coffee was delicious. The staff was great. Easiest check in ever."

Reviewed on 15 Aug, 2025

Holiday Inn Express Horse Cave by IHG
See all 459 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 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.