Hillsboro Vacations from $559
Book a Hotel + Flight or Car together to unlock savings
The Latest Hillsboro vacation packages
Price found within the past 48 hours. Click for updated prices.
Elwood Hotel & Suites
$559
per person
Nov 5 - Nov 7
found 1 day ago
Roundtrip flight included
New York (NYC) to Lexington (LEX)
9.6/10 Exceptional! (1,170 reviews)
Always our go to place in Lexington. We did have some very disruptive wild kids in the room across the hall causing their mama all kinds of hell but she got them quieted down by 9pm. Nothing on Elmwood except thin walls. That can happen anywhere.
Reviewed on Oct 3, 2026
Montgomery Inn BnB
$571
per person
Nov 5 - Nov 7
found 1 day ago
Roundtrip flight included
New York (NYC) to Lexington (LEX)
9.4/10 Exceptional! (119 reviews)
The room was unclean with visible dust and cobwebs in multiple locations. I killed three spiders…. one IN the bed, one in the shower and one on the coffee station. I checked out a day early because the room smelled strongly of mold… so much so, that I sneezed and coughed all night and woke up sick!! Management never even offered up an apology. I would never stay here again or recommend it to anybody.
Reviewed on Sep 30, 2026
Hillsboro Hotel Deals
Beautiful Country Sunsets I
Hillsboro KY
$135 nightly
$145 total
Oct 14 - Oct 15
Total with taxes and fees
9.6/10 Exceptional! (69 reviews)
"This was our second stay at this property. Just as with the first stay, very tidy, great atmosphere, the host was very friendly and accommodating, the sunsets were amazing,the stars at night were incredible, and the privacy was second to none. I highly recommend this property and host! Hoping to ..."
Reviewed on Sep 7, 2026
Holiday Inn Express and Suites Morehead by IHG
2650 KY 801 North Morehead KY
Fully refundable
$111 nightly
$122 total
Nov 1 - Nov 2
Total with taxes and fees
9/10 Wonderful! (947 reviews)
"Very clean just a good Post stay highly recommend"
Reviewed on Oct 3, 2026
Ramada Limited Mount Sterling
115 Stone Trace Dr Mount Sterling KY
Fully refundableReserve now, pay when you stay
$67 nightly
$74 total
Nov 1 - Nov 2
Total with taxes and fees
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 Hillsboro Vacation Packages
Hillsboro Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Fleming County Recreation Park and Fleming County Golf Association |
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Frequently asked questions
How much does a Hillsboro vacation package cost?
Offering excellent value package deals from $559 on Expedia, you'll be pleasantly surprised at how much a vacation to Hillsboro costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Hillsboro?
If you'd like to score a cheap Hillsboro vacation package, consider planning a trip in November, December and January. You'll usually find lower rates on hotels and airfares during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Hillsboro?
Usually, a handful of days is enough to check out the main attractions during your Hillsboro vacation. But if you'd like to have time to kick back or go on day tours, think about extending your itinerary.
How to find the best Hillsboro package deals?
Use Expedia's filters to find some fabulous Hillsboro package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Hillsboro package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Hillsboro vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still have the freedom to create a personalized Hillsboro vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Hillsboro?
Secure incredible bargains by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Hillsboro trip.
Does Expedia offer Book Now, Pay Later Hillsboro vacation packages?
If you're anything like us, you love going away but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the overall cost of your Hillsboro break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.