Drakesboro Vacations from $244

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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
per person
Aug 22 - Aug 25
found 13 hours ago
Roundtrip flight included
New York (NYC) to Owensboro (OWB)
9/10 Wonderful! (193 reviews)
Nice employees property was nice easy walking very beautiful

Reviewed on Jul 12, 2025

Shady Cliff Resort

Shady Cliff Resort

3 out of 5
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Owensboro (OWB)
8.8/10 Excellent! (39 reviews)
It was clean. Beds ok. Booking said there’d be a breakfast but restaurant was closed. Had to find a town with one. Challenging especially on a Sunday. Wasn’t horrible, but wouldn’t go back.

Reviewed on Jun 8, 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
$81 nightly
The price is $93 total per night from Jul 20 to Jul 21
$93 total
Jul 20 - Jul 21
Total includes taxes and fees
7.4/10 Good! (264 reviews)
Very good for price
"It was great. I was worried about the jetted tub being super clean but it didnt appear dirty but you always wonder. Everything else was very clean. Only issue when we were trying to check out no one was to be found and we had to wait a while, and if you're out late, good luck getting parking on a ..."

Reviewed on Jul 6, 2025

Days Inn by Wyndham Central City
Super 8 by Wyndham Central City
Super 8 by Wyndham Central City
2 out of 5
635 S 2nd St, Central City, KY
$77 nightly
The price is $89 total per night from Jul 29 to Jul 30
$89 total
Jul 29 - Jul 30
Total includes taxes and fees
7.4/10 Good! (418 reviews)
"Good place to stay."

Reviewed on Jun 9, 2025

Super 8 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
$62 nightly
The price is $68 total per night from Jul 16 to Jul 17
$68 total
Jul 16 - Jul 17
Total includes taxes and fees
6.4/10 (159 reviews)
"It was a great stay nice managers and staff i woukd go back agai"

Reviewed on Jun 21, 2025

Happy Stay Inn Madisonville I-69 By OYO
See all 55 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.

Find the Best Drakesboro Vacation Packages

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 $244 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.