Olive Hill Vacations from $469

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Your Olive Hill Vacation

Choose a Olive Hill vacation package and focus on what counts — having fun. There's no more planning stresses, just more free time to uncover the delights of this fascinating city, such as its family-friendly attractions and lively atmosphere. Carter Caves State Park and Carter Caves State Park Golf Course are some of the main attractions to check out during your trip to Olive Hill. A couple of clicks is all it takes to put together a tailor-made Olive Hill vacation on Expedia.

The Latest Olive Hill vacation packages

Price found within the past 48 hours. Click for updated prices.
Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 out of 5
Price was $541, price is now $469 per person
$469
per person
Sep 27 - Sep 30
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Lexington (LEX)
9.4/10 Exceptional! (1,005 reviews)
The man that checked us in was rude unfortunately with this being our first visit to this hotel we were not impressed by our “welcome.” He seemed as if someone had made him mad or he didn’t want to be there working and that carried over into our check in. Very unfortunate bc this was our first stay at this hotel and likely will be our last bc we felt uncomfortable and unwelcome.

Reviewed on Jul 13, 2026

Beautiful House in Nicholasville

Beautiful House in Nicholasville

2 out of 5
Price was $2,208, price is now $1,800 per person
$1,800
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
New Orleans (MSY) to Lexington (LEX)
No reviews

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was $607, price is now $509 per person
$509
per person
Sep 27 - Sep 30
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Lexington (LEX)
8.8/10 Excellent! (1,004 reviews)
The hotel has a cool concept, and the renovations to the building were largely thoughtful. The rooms were ok, bathrooms were great. Overall was a 4 out of 5.

Reviewed on Jul 10, 2026

DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
Price was $576, price is now $491 per person
$491
per person
Sep 27 - Sep 30
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Lexington (LEX)
8.8/10 Excellent! (1,004 reviews)
Overall, it was a great stay! Love the design and decor! Only issue was issues with the AC. I had to call for maintenance twice to fix the AC. They responded but it was still very inconvenient due to the extremely hot temperatures!

Reviewed on Jul 14, 2026

Marriott Lexington Griffin Gate Golf Resort & Spa

Marriott Lexington Griffin Gate Golf Resort & Spa

4.5 out of 5
Price was $668, price is now $575 per person
$575
per person
Sep 27 - Sep 30
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Lexington (LEX)
8.4/10 Very Good! (717 reviews)
Everything was great.

Reviewed on Jul 11, 2026

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Stay near popular Olive Hill attractions

A rocky cave entrance surrounded by large boulders and greenery.

Carter Caves State Park

9.2/10 (148 reviews)
This Kentucky wonderland houses over 20 caverns, including Cascade Cave with its 30-foot underground waterfall. Explore on guided tours ranging from easy walks to adventurous crawls through the limestone labyrinth.
See properties

Olive Hill Hotel Deals

Carter Caves State Resort Park

Carter Caves State Resort Park

3 out of 5
344 Caveland Dr Olive Hill KY
$96 nightly
The price is $106 total per night from Aug 2 to Aug 3
$106 total
Aug 2 - Aug 3
Total with taxes and fees
9.2/10 Wonderful! (761 reviews)
"The cottages were decent. The mattresses were very hard but everything else was good. The employees were beyond helpful and the area is just beautiful."

Reviewed on Jul 13, 2026

Carter Caves State Resort Park
Fairfield Inn & Suites By Marriott Ashland

Fairfield Inn & Suites By Marriott Ashland

3 out of 5
10945 Route 60 Ashland KY
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $116 total per night from Jul 19 to Jul 20
$116 total
Jul 19 - Jul 20
Total with taxes and fees
8.2/10 Very Good! (778 reviews)
"Older hotel but it was satisfactory"

Reviewed on Jul 14, 2026

Fairfield Inn & Suites By Marriott Ashland
Holiday Inn Express and Suites Morehead by IHG

Holiday Inn Express and Suites Morehead by IHG

2.5 out of 5
2650 KY 801 North Morehead KY
Fully refundable
$169 nightly
The price is $186 total per night from Aug 12 to Aug 13
$186 total
Aug 12 - Aug 13
Total with taxes and fees
9/10 Wonderful! (926 reviews)
"The staff were very friendly and helpful. The outdoor pool was good and the breakfast was delicious."

Reviewed on Jul 14, 2026

Holiday Inn Express and Suites Morehead by IHG
See all 162 properties in Olive Hill
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 Olive Hill Vacation Packages

Olive Hill Essential Information

Language
English
Currency
U.S dollars
Population
1,600
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Carter Caves State Park, Grayson Lake State Park and Carter Caves State Park Golf Course

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Frequently asked questions

How much does an Olive Hill vacation package cost?
You can pick up a vacation package to this top destination from $469 on Expedia. But how much your vacation to Olive Hill costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Olive Hill?
If you're looking to snag a cheap Olive Hill vacation package, consider traveling in February, October and December. You'll generally find better rates on hotels and airfares during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Olive Hill?
Usually, a handful of days is enough to visit the top attractions during your Olive Hill vacation. But if you prefer to have some time to rest or take day trips, consider extending your trip.
How to find the best Olive Hill package deals?
Use Expedia's filters to find some great Olive Hill package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Olive Hill package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book an Olive Hill vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and stays separately. Better still, you can tailor your Olive Hill trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Olive Hill?
If you're planning a spur-of-the-moment Olive Hill trip, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find terrific deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Olive Hill vacation packages?
If you're like us, you love going away but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Olive Hill trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.

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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.