Olive Hill Vacations from $582

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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.
Comfort Inn & Suites Springfield

Comfort Inn & Suites Springfield

2 out of 5
Price was $607, price is now $582 per person
$582
per person
Jan 14 - Jan 19
found 14 hours ago
Roundtrip non-stop flight included
New York (JFK) to Lexington (LEX)
6.6/10 (143 reviews)
This hotel is exactly what you need if you want a no-frills, clean place to stay while traveling. The price is good and the place is comfortable.

Reviewed on Oct 30, 2026

Wildflower Ranch Inn

Wildflower Ranch Inn

3.5 out of 5
Price was $993, price is now $810 per person
$810
per person
Jan 14 - Jan 19
found 14 hours ago
Roundtrip non-stop flight included
New York (JFK) to Lexington (LEX)
9.2/10 Wonderful! (24 reviews)
Carol and Rich were wonderful hosts! They made sure we had everything we needed, were very accommodating, and served 5 star breakfasts. The pool was sublime, the sun room was magical. We can’t say enough about how special we felt during our stay!

Reviewed on Aug 17, 2026

Hill House B&B

Hill House B&B

2 out of 5
Price was $881, price is now $822 per person
$822
per person
Jan 14 - Jan 19
found 14 hours ago
Roundtrip non-stop flight included
New York (JFK) to Lexington (LEX)
10/10 Exceptional! (21 reviews)
Beautiful home! Super clean and cozy! Jim and Cheryl were amazing. We went for only 1 night but had the best time. The hosts are very welcoming and friendly., and the breakfast was fantastic! . Thank you both so much for your hospitality! We will definitely be back! I may never stay at a hotel again!

Reviewed on Nov 8, 2026

Hampton Inn Lebanon

Hampton Inn Lebanon

2.5 out of 5
Price was $726, price is now $697 per person
$697
per person
Jan 14 - Jan 19
found 14 hours ago
Roundtrip non-stop flight included
New York (JFK) to Lexington (LEX)
8.6/10 Excellent! (588 reviews)

Maple Hill Manor

Maple Hill Manor

3.5 out of 5
Price was $862, price is now $862 per person
$862
per person
Jan 14 - Jan 19
found 14 hours ago
Roundtrip non-stop flight included
New York (JFK) to Lexington (LEX)
9.4/10 Exceptional! (651 reviews)
Beautiful and charming accommodations! Unique experience stepping into history. Breakfast and the night time dessert were fantastic.

Reviewed on Sep 29, 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.
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Olive Hill Hotel Deals

Carter Caves State Resort Park

Carter Caves State Resort Park

3 out of 5
344 Caveland Dr Olive Hill KY
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Carter Caves State Resort Park
Days Inn by Wyndham Grayson

Days Inn by Wyndham Grayson

2 out of 5
650 CW Stevens Blvd Grayson KY
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $98 total per night from Nov 15 to Nov 16
$98 total
Nov 15 - Nov 16
Total with taxes and fees
9/10 Wonderful! (467 reviews)
"All went well - surprised though that the bathroom sink was super slow draining - don't that have drano on site?"

Reviewed on Nov 10, 2026

Days Inn by Wyndham Grayson
Best Western Eagles Inn

Best Western Eagles Inn

2.5 out of 5
110 Toms Dr Morehead KY
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $142 total per night from Nov 27 to Nov 28
$142 total
Nov 27 - Nov 28
Total with taxes and fees
8.8/10 Excellent! (844 reviews)
"Clean and nice staff"

Reviewed on Nov 11, 2026

Best Western Eagles Inn
See all 165 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 $582 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.