Eastern Kentucky Holidays

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Your Eastern Kentucky Holiday

When you're ready for your next epic adventure, our Eastern Kentucky holiday packages are the answer. If you're making your way to Middlesboro, walking trails and culture are among the many things that make this city truly special. Your trip to Eastern Kentucky wouldn't be complete without spending some time in its leading cities, starting with London. Some of the most popular attractions here include Wood Creek Lake and London Dragway. Corbin is another favourite with Eastern Kentucky travellers. Visitors to this exciting destination enjoy The Arena at SE KY Agricultural and Expo Complex and Corbin Municipal Golf Course. From the instant you book your Eastern Kentucky holiday to the second you come back home, Expedia has your back each step of the way.

Eastern Kentucky Holiday Packages

Untamed wilderness unfurls throughout this easterly region, where you’ll find thundering waterfalls, mountain trails and tranquil forest retreats.

Experience some of Kentucky’s most stunning landscapes in the wild region of Eastern Kentucky. With Appalachian peaks and lush valleys carved by wild rivers, you’ll find magnificent scenery in Kentucky’s great outdoors. Visit quaint towns and learn about the rich tradition of arts, crafts and country music in the cosy townships. See the breathtaking works of nature in national forests, state parks and the Kentucky Appalachians.

The Appalachians stretch across Kentucky’s northeastern border. Explore this mountainous region’s beautiful reserves via a network of trails suitable for hiking, RV driving and horseback riding. Check out Broke Leg Falls or the serene beauty of the Red River Gorge. Go fishing or boating on the pretty lakes or tour the intriguing geological formations at Carters Caves State Resort Park.

The Highlands Museum and Discovery Centre and the Kentucky Folk Arts Centre present an insight into regional arts, history and crafts. Appalachian music is honored at the US 23 Country Music Highway Museum, as well as numerous festivals held throughout the region.

Further south, you’ll find nature’s splendour in Daniel Boone Country and the Cumberland Falls State Park. Kayak along the river or camp with a riverside vista. Don’t miss the intriguing phenomenon that appears on moonlit nights at Cumberland Falls, a beautiful cascade known as the Niagara of the South. You can also go rock climbing at Torrent Falls or explore the thrilling trails at the Black Mountain Off-Road Adventure Park. Charming Renfro Valley is the home of the “Grand Ole Opry of Kentucky” and numerous country music, comedy and entertainment events. Learn about the historic expedition through the Cumberland Gap in 1750 at the preserved cabin of the trip’s leader, Dr. Thomas Walker.

Reach the breathtaking landscapes of Eastern Kentucky by flying into Lexington’s Bluegrass Airport, which is situated within a few hours’ drive of many Eastern Kentucky attractions. Interstate highways stretch across the region’s northerly and westerly borders from Lexington.

Whether you camp out or stay in a cabin or cosy motel room, you’ll feel revitalized after a visit to Eastern Kentucky.

Eastern Kentucky Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tri-State Airport (HTS)

Top hotels in Eastern Kentucky

Natural Bridge State Resort Park

Natural Bridge State Resort Park

2135 Natural Bridge Road Slade KY
£82
30 Sept - 1 Oct
includes taxes & fees
8.6/10 Excellent! (2,061 reviews)
"The room we had needs a lot of cleaning and a check of the air conditioning system. Couldn’t get the air to go any lower than 70 degrees. Bathroom needs new caulking and grout. Carpeting needs to be replaced and the vents in the bathroom need to be cleaned"

Reviewed on 20 Sept 2026

Natural Bridge State Resort Park
Country Inn & Suites by Radisson, London, KY

Country Inn & Suites by Radisson, London, KY

2035 Highway 192 West London KY
Fully refundable
£71
11 Oct - 12 Oct
includes taxes & fees
8/10 Very good! (1,003 reviews)
"Great & clean place."

Reviewed on 21 Sept 2026

Country Inn & Suites by Radisson, London, KY
The Landmark Hotel

The Landmark Hotel

190 S Mayo Trail Pikeville KY
Fully refundableReserve now, pay when you stay
£76
23 Sept - 24 Sept
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Staff very positive & helpful. Facility build in ‘64 minor old odor. Room rate reasonable- likely to stay again. Bathroom small."

Reviewed on 20 Sept 2026

The Landmark Hotel
See all 878 properties in Eastern Kentucky
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Stay near popular Eastern Kentucky attractions

A forest with autumn foliage, a rocky outcrop, and a cloudy sky.

Red River Gorge

9.6/10 (460 reviews)
Commune with nature and explore the great outdoors at Red River Gorge during your travels in Wellington. Amble around this relaxing area's riverfront or seek out the hiking trails.
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A waterfall with two kayakers in red kayaks.
Photo by www.kentuckytourism.com

Cumberland Falls

9.6/10 (642 reviews)
Gaze in awe at Kentucky’s own Niagara of the South, where a stunning cascade creates a unique natural phenomenon on brightly moonlit nights.
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University of the Cumberlands

8.8/10 (61 reviews)
Enjoy the student vibe at University of the Cumberlands during your visit to Williamsburg. Discover the restaurants and museums in this family-friendly area.
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Black Mountain Offroad Adventure Area - Putney Trailhead

10.0/10 (4 reviews)
You can take time to visit Black Mountain Offroad Adventure Area - Putney Trailhead during your travels to Putney. Wander the lakeside or discover the area's mountain views.
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Kentucky Splash Water Park

7.6/10 (59 reviews)
Bring the family to Kentucky Splash Water Park and have a fun-filled day at this theme park in Williamsburg. While in this family-friendly area, you can savour the top-notch restaurants.
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Frequently asked questions

Why should I book my Eastern Kentucky holiday with Expedia?
Expedia has you covered for all aspects of your upcoming Eastern Kentucky getaway. You'll always get the best prices, but when you bundle your airfares, accommodation and/or hire car into a holiday package, you'll score even bigger savings. Looking to really make the most of your stay? Add some awesome activities and tours to your customised package. Expedia offers flexible cancellation policies on almost all bookings, so there's no need to stress if your travel plans change. Head over to our Customer Service Portal link to learn more.
When is the best time of year to holiday in Eastern Kentucky?
Eastern Kentucky is at its busiest in March, July and August. If you want a more laid-back escape, visit in November, December and January. Arrange your trip to Eastern Kentucky based on what type of holiday you want. January is the coolest time of year, when daytime temperatures average 1ºC. In July, the warmest period, you'll experience temperatures of around 23ºC during the day.
What are the top hotels for my holiday in Eastern Kentucky?
Check out Hot Tub & WiFi - Large Family Cabin - Climbers Haven - Red River Gorge, Kentucky! and WiFi & Adventure - Large Family-Friendly Cabin - Starlight Cabin - Red River Gorge, Kentucky!. They're top picks for many travellers headed to Rogers. If Campton features in your travel plans, Newly built large cabin and Hot Tub, Firepit, WiFi, Cabin in Red River Gorge Lake are both popular options.
How do I get a cheap holiday to Eastern Kentucky?
Bundle your bookings with Expedia to save on your next big adventure. With over 400 partner airlines and 321,000 hotel options worldwide, your Eastern Kentucky holiday can be customised exactly to suit your travel style. With all those extra pounds, why not throw in a few fun tours and activities? It's an easy way to unlock even more discounts. Your dream getaway to Eastern Kentucky is closer than you thought! Learn more about how you can save money on your holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Eastern Kentucky holiday?
Discover leading attractions like U.S. 23 Country Music Highway Museum, Natural Bridge State Park, Cumberland Falls and Red River Gorge Geological Area. With so many exciting things to see and do, your holiday in Eastern Kentucky will be unforgettable.
What is the best city to stay in when on holiday in Eastern Kentucky?
U.S. 23 Country Music Highway Museum is one of the main attractions that attract visitors to Eastern Kentucky, so it makes perfect sense that many decide to holiday in Staffordsville.
Do I need a visa for my Eastern Kentucky holiday?
Official government websites will have all the information you need on visa requirements, application procedures and necessary documentation. Your nationality and reason for travelling, whether it be for tourism or business, will determine if you'll need a visa for Eastern Kentucky. Also check that your passport is up to date and has at least six months validity remaining after the date of your intended return. Finalise all your travel planning well ahead of time to avoid any last-minute surprises.
What should I wear on my Eastern Kentucky holiday?
Consider the types of activities you'll be doing during your Eastern Kentucky trip and select versatile pieces that you can easily mix and match. For fashion inspiration or information on any dress codes, browse style blogs or social media accounts. In Eastern Kentucky, daytime average temperatures reach 23ºC during July, making it the warmest month. January is the coolest time of year here, with the mercury hovering around 1ºC during the day. Make packing a breeze by monitoring the forecast for each place on your itinerary.
What does an Expedia Eastern Kentucky holiday include?
Flights, hotels and car hires, or any combination of the three — you decide! Whether you're exploring Eastern Kentucky with the entire family or enjoying a solo break, there's a package to fit every style and budget. Once you've made your booking, why not add on some tours and experiences? Expedia has many types of properties in Eastern Kentucky, providing you with the freedom and flexibility to customise your holiday. Cabins and private holiday homes are two of the most-favoured stays for our guests here.
Does Expedia offer Book Now, Pay Later Eastern Kentucky holidays?
Yes. Expedia has teamed up with online lender Klarna to help you conveniently pay for your holiday in instalments. Simply pick the payment plan best suited to your needs during the checkout process and take away the stress of budgeting for your trip. Make sure you bundle your flights, car hire and hotel with Expedia to get the biggest bang for your buck. Browse our flexible payment options below:
  • Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's convenient monthly instalment plans. If paying across multiple instalments sounds right for you, pick this option during the checkout process.
  • No-deposit holidays: If no upfront fee for your getaway makes pressing that "book now" button more stress-free, choose a no-deposit holiday plan from Klarna so you can Book Now, Pay Later!
Can I choose my airline with an Eastern Kentucky Expedia holiday?
Yes — that's the beauty of an Expedia holiday package. You're in charge! We have access to more than 400 partner airlines worldwide, so you have loads of choice when creating your Eastern Kentucky adventure.

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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. Flight-inclusive packages are ATOL protected.