Olive Hill Vacation Packages 2026 from $532

Olive Hill flight + hotel vacation packages

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

GuestHouse Lexington

$532

per person

Jul 10 - Jul 13

just found

Roundtrip non-stop flight included

Charleston (CHS) to Lexington (LEX)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the indoor pool and conveniences like a 24-hour front desk and laundry facilities.

21c Museum Hotel Lexington

Downtown Lexington

$687

per person

Jul 10 - Jul 13

just found

Roundtrip non-stop flight included

Charleston (CHS) to Lexington (LEX)

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

Capital Plaza Hotel

$572

per person

Jul 10 - Jul 13

just found

Roundtrip non-stop flight included

Charleston (CHS) to Lexington (LEX)

This hotel features a restaurant, an indoor pool, and a bar/lounge. There's a gym on site, and laundry facilities and concierge services are also offered.

Country Inn & Suites by Radisson, Georgetown, KY

$537

per person

Jun 13 - Jun 16

found 1 day ago

Roundtrip non-stop flight included

Charleston (CHS) to Lexington (LEX)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

Montgomery Inn BnB

$666

per person

Jun 13 - Jun 16

found 1 day ago

Roundtrip non-stop flight included

Charleston (CHS) to Lexington (LEX)

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free full breakfast each morning. A terrace, a garden, and a lobby fireplace 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

$85 nightly

$94 total

Apr 30 - May 1

Total with 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

Fairfield Inn & Suites By Marriott Ashland

10945 Route 60 Ashland KY

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$106 total

May 3 - May 4

Total with 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

Days Inn by Wyndham Grayson

650 CW Stevens Blvd Grayson KY

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$98 total

Apr 30 - May 1

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Breakfast included

Parking included

Newly renovated 2 bedroom cabin near Cave Run Lake & Red River Gorge

Wellington KY

$190 nightly

$211 total

Apr 30 - May 1

Total with taxes and fees

This cabin featured laundry facilities and barbecue grills.

Kitchen

Washer

Days Inn by Wyndham Ashland

12700 Route 180 Ashland KY

Free Cancellation

Reserve now, pay when you stay

$77 nightly

$87 total

May 17 - May 18

Total with 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. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Pet friendly

Best Western Eagles Inn

110 Toms Dr Morehead KY

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$132 total

May 17 - May 18

Total with 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

Don't see what you're looking for?

See all available properties in Olive Hill

View all properties

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

Carter Caves State Park

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.

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

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 $532. 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.