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Harlan County Holiday Rentals

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Top Holiday Rentals Destinations in Harlan County

4BR 2 bath house with full kitchen, living room, hot tub and game room.

10.0 out of 10, Exceptional, (2)
"Nice place great for rzr riding "
4BR 2 bath house with full kitchen, living room, hot tub and game room.

Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)

8.8 out of 10, Excellent, (3)
"We will rent this property again :)"
Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)

Pappy's Coal Miner's Cabin

10.0 out of 10, Exceptional, (1)
"Only problem I saw was no chlorine tablets in hot tub other than that perfect stay"
Pappy's Coal Miner's Cabin

Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion)

10.0 out of 10, Exceptional, (1)
"Had a few issues but they were resolved."
Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion)

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

10.0 out of 10, Exceptional, (15)
"Our group had a wonderful time staying at Uncle Ernie's! Everything was neat, tidy, and felt like home. We definitely will be back next time we are in the area!"
The price is NZ$361
includes taxes & fees
30 Sept - 1 Oct
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

Small Town Charmer - Rent Entire Home

10.0 out of 10, Exceptional, (63)
"We had a wonderful stay at this beautiful house! The home itself was spotless, well-maintained, and full of charm. One of our favorite features was the lovely back porch—perfect for relaxing in the morning with coffee or winding down in the evening.The location was central and convenient, with easy access to nearby lakes and only about two hours from both the Kentucky Horse Park and Natural Bridge State Resort Park. It made for a perfect base for day trips and outdoor adventures.Would definitely...
Small Town Charmer - Rent Entire Home

1928 Home in the heart of Cumberland Gap

9.8 out of 10, Exceptional, (91)
"Prominent house in historic Cumberland Gap.Family friendly and comfortable accommodations. Lots of different seating options inside and out. We would stay here again."
1928 Home in the heart of Cumberland Gap

Direct Access to Waterfall/Creek Trail of Leatherwood Off Road Park

10.0 out of 10, Exceptional, (5)
"Very cute house with everything you need"
Direct Access to Waterfall/Creek Trail of Leatherwood Off Road Park

Secluded cabin on the Clinch river, kayaks & canoes available! Sleeps 6. WIFI.

2.0 star property
9.6 out of 10, Exceptional, (8)
"It was a great place would love to stay again perfect for my little family "
The price is NZ$287
includes taxes & fees
1 Oct - 2 Oct
Secluded cabin on the Clinch river, kayaks & canoes available! Sleeps 6. WIFI.

Cabin 1, Cozy Cottage with WiFi, Fireplace and Whirlpool Tub in Duffield, VA

10.0 out of 10, Exceptional, (3)
"Cabin was very clean and well stocked and in a beautiful setting. We really enjoyed our stay. Thanks !"
Cabin 1, Cozy Cottage with WiFi, Fireplace and Whirlpool Tub in Duffield, VA

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

10.0 out of 10, Exceptional, (1)
The price is NZ$342
includes taxes & fees
1 Oct - 2 Oct
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

Blissful Bungalow across from LMU campus

9.6 out of 10, Exceptional, (25)
"visiting family at lmu, very close! We had a great weekend, would stay again! "
The price is NZ$400
includes taxes & fees
29 Sept - 30 Sept
Blissful Bungalow across from LMU campus

Harrogate Home Mountain View’s Dog Friendly

9.8 out of 10, Exceptional, (20)
"Good space for me, my family, and my dogs to crash while we did a quick visit to the Gap."
The price is NZ$520
includes taxes & fees
29 Sept - 30 Sept
Harrogate Home Mountain View’s Dog Friendly

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

9.2 out of 10, Wonderful, (39)
"Just as advertised. Very quiet and enjoyable stay!"
The price is NZ$364
includes taxes & fees
2 Oct - 3 Oct
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Spacious and Accessible 2 BR Cabin in Duffield, VA near Devil's Bathtub

9.0 out of 10, Wonderful, (2)
"Great spot to explore the area!!"
Spacious and Accessible 2 BR Cabin in Duffield, VA near Devil's Bathtub

3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre

4.8 out of 10, (3)
"I did not stay at this property due to a double booking. I stayed at a nearby house that needs to be cleaned better, specially the floors, a shower curtain needs to be added to the beautiful update in bathroom, some plates woukd be nice. House rules and check in, check out procedures, places to visit and eat nearby would have been helpful to have posted at the house. Overall was a decent place to stay, quiet neighborhood. I would at least consider staying again."
The price is NZ$399
includes taxes & fees
29 Sept - 30 Sept
3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre

Cozy log cabin near Pennington Gap and Jonesville, VA known as "The Duck Pond"

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great cabin and beautiful location!!!"
Cozy log cabin near Pennington Gap and Jonesville, VA known as "The Duck Pond"

Tiny Treehouse Escape with Wi-Fi, Modern Amenities, BBQ Deck + Mountain Views

10.0 out of 10, Exceptional, (2)
"My friends and I had a wonderful time.It’s a very clean, peaceful and pretty place to stay!I would definitely recommend it to anyone who is looking for a nice getaway!"
The price is NZ$450
includes taxes & fees
29 Sept - 30 Sept
Tiny Treehouse Escape with Wi-Fi, Modern Amenities, BBQ Deck + Mountain Views

Welcoming 3-bedroom house with AC in charming Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro

The House on Park Avenue

3.5 star property
The price is NZ$692
includes taxes & fees
29 Sept - 30 Sept
The House on Park Avenue
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.
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Top Harlan County Hotel Reviews

Find out more about Harlan County

Find out more about Harlan County

Everything you need to know about Harlan County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Harlan County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Harlan County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Harlan County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Harlan County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Harlan County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Harlan County holiday rentals we have selected for you start as low as NZ$287 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Harlan County rentals

At Expedia, we put the best Harlan County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Harlan County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Harlan County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Harlan County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia