Olive Hill Vacation Packages 2025 from $468

Olive Hill flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Home2 Suites by Hilton Lexington University / Medical Center

Zandale

per person

Aug 12 - Aug 16

found 4 hours ago

Roundtrip non-stop flight included

Pensacola (PNS) to Lexington (LEX)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free continental breakfast each morning.

The Sire Hotel Lexington, Tapestry Collection by Hilton

Downtown Lexington

per person

Aug 12 - Aug 16

found 4 hours ago

Roundtrip non-stop flight included

Pensacola (PNS) to Lexington (LEX)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a 24-hour business center, and a terrace are also offered.

The Manchester

Distillery District

per person

Aug 12 - Aug 16

found 4 hours ago

Roundtrip non-stop flight included

Pensacola (PNS) to Lexington (LEX)

This smoke-free hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. WiFi in public areas is free. Valet parking, express check-in, and express check-out are also offered.

Home2 Suites by Hilton Georgetown

per person

Aug 12 - Aug 16

found 4 hours ago

Roundtrip non-stop flight included

Pensacola (PNS) to Lexington (LEX)

This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Elwood Hotel & Suites

per person

Aug 12 - Aug 16

found 4 hours ago

Roundtrip non-stop flight included

Pensacola (PNS) to Lexington (LEX)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A lobby fireplace, express check-out, and dry cleaning are also on offer.

Top Olive Hill hotels deals

Carter Caves State Resort Park

344 Caveland Dr, Olive Hill, KY

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$117 total

Jun 15 - Jun 16

Total includes taxes and fees

This hotel features an outdoor pool, an outdoor tennis court, and a restaurant. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.

Pool

Pet friendly

Cozy Country FarmHouse GetAway - Yet Minutes to a small Town

Get rates

This farm stay featured laundry facilities and barbecue grills.

Free WiFi

Air conditioning

Fairfield Inn & Suites By Marriott Ashland

10945 Route 60, Ashland, KY

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$91 total

Jun 15 - Jun 16

Total includes taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Pool

Breakfast included

SureStay by Best Western Grayson

501 C W Stevens Boulevard, Grayson, KY

Free Cancellation

Reserve now, pay when you stay

$92 nightly

$105 total

Jun 8 - Jun 9

Total includes taxes and fees

An indoor pool, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A fireplace in the lobby and a computer station are also provided.

Pool

Breakfast included

Best Western Eagles Inn

110 Toms Dr, Morehead, KY

Free Cancellation

Reserve now, pay when you stay

$102 nightly

$113 total

Jun 22 - Jun 23

Total includes taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Days Inn by Wyndham Ashland

12700 Route 180, I-64 and Route 180 Exit 185, Ashland, KY

Free Cancellation

Reserve now, pay when you stay

$71 nightly

$81 total

Jun 29 - Jun 30

Total includes taxes and fees

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. A safe deposit box and laundry facilities are also provided.

Breakfast included

Pet friendly

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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.

Popular places to visit

This is a lovely place in Eastern Kentucky! #lifeatexpedia

Carter Caves State Park

4.5/5(36 reviews)

Commune with nature and explore the great outdoors at Carter Caves State Park during your travels in Olive Hill. While you're in the area, wander around the parks.

Greyson Lake.. A beautiful place located in Kentucky where you can jump on in your bathing suit and start swimming, hop in a kayak, throw your tennis shoes on and start hiking, or simply go cliff jumping off some of the beautiful rocks there. Highly recommend it to anyone looking for an adventurous day. #AquaTrove Everyone please help me win.

Grayson Lake State Park

You can take time to visit Grayson Lake State Park during your travels to Olive Hill. While you're in the area, wander around the natural setting.

Bat Cave and Cascade Caverns

4.5/5(10 reviews)

Explore the great outdoors at Bat Cave and Cascade Caverns, a lovely green space in Olive Hill. While you're in the area, wander around the natural setting.

Frequently asked questions

How much are vacation packages to Olive Hill?

With Travelocity vacation packages, you can be living it up in Olive Hill for as little as $468. Activities, flights and hotels — we’ve got you covered. You can save some cash just by combining your bookings together. With everything taken care of before leaving, you can sit back, relax and not worry about a thing.

How long should my Olive Hill vacation be?

Many travelers pack their suitcase and kick back in Olive Hill for approximately 2 nights. That gives you an idea of time frames, but don’t be limited by it. Whether you just stay for a few days to see the major sights or settle in to explore new places, an unforgettable journey awaits.

Where can I get the best vacation package deals for Olive Hill?

For an amazing Olive Hill package deal, turn to Travelocity. Choose from 400 air carriers and 1,000,000 properties around the world to create your dream escape — it’s really that easy.

Why should I purchase my Olive Hill vacation bundle with Travelocity?

Incredible savings, an abundance of enticing destinations and a team of customer service experts available 24/7 — that’s why. And with our Price Match Guarantee, you can rest easy knowing that you’ll always get the best possible deal with Travelocity.

Can I save money on my Olive Hill car rental if I bundle it with my hotel or flight?

Combining your hotel, car and flight into an Olive Hill vacation package is the easiest way to score the best deal. Plus, having your own set of wheels gives you the freedom to get to all those famous sights you’re itching to see. Situated 30 mi from Olive Hill, Paramount Arts Center is one place that should be on your agenda. Buckle up and make a day trip of it.

Which airport is best for Olive Hill?

Tri-State Airport (HTS) is 35 mi east of inner Olive Hill.

What is there to do in Olive Hill?

You’ll sense a certain magic as you roam the streets of Olive Hill. Carter Caves State Park and Grayson Lake State Park are just a couple of renowned sights that lure visitors to this fantastic city, so add them to your travel itinerary.

Where should I stay when visiting Olive Hill?

Many travelers check in to the Carter Caves State Resort Park. It’s sure to be a great base for your Olive Hill escape.