Drakesboro Vacations from $258

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The Latest Drakesboro vacation packages

Price found within the past 48 hours. Click for updated prices.
The Lodge at Mammoth Cave

The Lodge at Mammoth Cave

2 out of 5
Price was $285, price is now $258 per person
$258
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Owensboro (OWB)
9/10 Wonderful! (287 reviews)
Charming historic cabin, beautiful setting, comfy bed, very kind and helpful front desk staff, excellent food in the restaurant. Very pleasant stay!

Reviewed on Oct 9, 2025

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Drakesboro Hotel Deals

Days Inn by Wyndham Central City

Days Inn by Wyndham Central City

2.5 out of 5
640 S 2nd St, Central City, KY
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $86 total per night from Oct 19 to Oct 20
$86 total
Oct 19 - Oct 20
Total with taxes and fees
7.2/10 Good! (274 reviews)
"The side door to the first floor has NO LOCK on it. The door looks like you have to use a room key BUT YOU DON’T. You can walk right in WITHOUT a KEY. Not very secure. Also the parking lot has pot holes in it. Not very becoming for place of business."

Reviewed on Sep 28, 2025

Days Inn by Wyndham Central City
Happy Stay Inn Madisonville I-69 By OYO

Happy Stay Inn Madisonville I-69 By OYO

2.5 out of 5
99 Free Henry Ford Rd, Madisonville, KY
Fully refundableReserve now, pay when you stay
$57 nightly
The price is $62 total per night from Oct 16 to Oct 17
$62 total
Oct 16 - Oct 17
Total with taxes and fees
6.2/10 (171 reviews)
"It was ok"

Reviewed on Oct 7, 2025

Happy Stay Inn Madisonville I-69 By OYO
Best Western Central City

Best Western Central City

2.5 out of 5
627 S 2nd St, Central City, KY
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $137 total per night from Oct 16 to Oct 17
$137 total
Oct 16 - Oct 17
Total with taxes and fees
8.4/10 Very Good! (227 reviews)
"Nice hotel. Plenty of parking."

Reviewed on Oct 6, 2025

Best Western Central City
See all 63 properties in Drakesboro
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.

Drakesboro Essential Information

Language
English
Currency
U.S dollars
Population
510

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Frequently asked questions

How much does a Drakesboro vacation package cost?
You can grab a vacation package to this top destination from $258 on Expedia. But how much your vacation to Drakesboro costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Drakesboro?
You can generally find reduced prices and better availability in January, June and July. Take a look at our cheap Drakesboro vacation packages and you could score some great off-season deals.
How many days is enough for Drakesboro?
Usually, a handful of days is enough to see the top attractions during your Drakesboro vacation. However, if you'd like to have some time to chill out or take day tours, think about extending your itinerary.
How to find the best Drakesboro package deals?
Start your search for a Drakesboro package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Drakesboro package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Drakesboro adventure off to a flying start.
Is it cheaper to book a Drakesboro vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component separately. And you'll still get the flexibility to create a personalized Drakesboro vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Drakesboro?
If you've got your Drakesboro travel dates finalized, book as soon as you can to grab some fantastic deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Drakesboro vacation packages?
Your Drakesboro break should be an escape from your daily routine, not a reason for money-related stress. So to allow you a bit more flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.