Olive Hill Vacation Packages 2026 from $312

Olive Hill flight + hotel vacation packages

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

Tru by Hilton University Medical Center

South Broadway Park

$312

per person

Jul 2 - Jul 5

found 19 hours ago

Roundtrip flight included

Charleston (CHS) to Lexington (LEX)

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

21c Museum Hotel Lexington

Downtown Lexington

$346

per person

Jul 2 - Jul 5

found 19 hours ago

Roundtrip 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.

The Sire Hotel Lexington, Tapestry Collection by Hilton

Downtown Lexington

$421

per person

Jul 2 - Jul 5

found 19 hours ago

Roundtrip 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. Self parking, a 24-hour business center, and a terrace are also offered.

Capital Plaza Hotel

$333

per person

Jul 2 - Jul 5

found 19 hours ago

Roundtrip 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.

Origin Lexington a Wyndham Hotel

$324

per person

Jul 2 - Jul 5

found 19 hours ago

Roundtrip flight included

Charleston (CHS) to Lexington (LEX)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 2 conference rooms, along with free WiFi in public areas. Free self parking and a coffee shop are also offered on site.

Top Olive Hill hotels deals

Carter Caves State Resort Park

344 Caveland Dr Olive Hill KY

$120 nightly

$132 total

Jun 3 - Jun 4

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

$103 nightly

$116 total

Jun 9 - Jun 10

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

Best Western Eagles Inn

110 Toms Dr Morehead KY

Free Cancellation

Reserve now, pay when you stay

$136 nightly

$151 total

Jun 8 - Jun 9

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

Greenbo Lake State Resort Park

965 Lodge Rd Greenup KY

$100 nightly

$110 total

Jun 3 - Jun 4

Total with taxes and fees

This lodge features a marina, 2 outdoor pools, and a restaurant. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.

Pool

Pet friendly

Days Inn by Wyndham Grayson

650 CW Stevens Blvd Grayson KY

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$98 total

Jun 7 - Jun 8

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

Days Inn by Wyndham Ashland

12700 Route 180 Ashland KY

Free Cancellation

Reserve now, pay when you stay

$76 nightly

$86 total

Jun 14 - Jun 15

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

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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

Carter Caves State Park

4.5/5(37 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.

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 $312. 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.