Oakland Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Oakland

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$181 per night from 2 Jul to 3 Jul
S$181
2 Jul - 3 Jul
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
Fine Family Spot near Mammoth Cave
"Great place to stay close to Mammoth Cave NP. Pool area is tired and no more hot tub, just FYI. Check-in staff member was really nice. Breakfast missed on a couple items (ran out of milk for cereal and the pancake machine didn’t work), but still had breakfast, which was efficient."

Reviewed on 23 Jun, 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 S$100 per night from 1 Jul to 2 Jul
S$100
1 Jul - 2 Jul
includes taxes & fees
8.2/10 Very Good! (260 reviews)
"Very clean, very professional. Room was ready and AC was on when we arrived."

Reviewed on 27 Jun, 2025

Woodspring Suites Bowling Green I-65
Holiday Inn University Plaza-Bowling Green by IHG
Holiday Inn University Plaza-Bowling Green by IHG
3 out of 5
1021 Wilkinson Trce, Bowling Green, KY
Fully refundable
The price is S$137 per night from 2 Jul to 3 Jul
S$137
2 Jul - 3 Jul
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
Great Spot in BGKY
"Excellent location with great rooms and plenty of near by dining options"

Reviewed on 27 Jun, 2025

Holiday Inn University Plaza-Bowling Green by IHG
See all 461 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.