Photo by Brittany Davidson

Harlan County Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Our top choices for Harlan County holiday rentals

Apartment in Harlan

Beautiful Loft in the Woods
10.0 out of 10, Exceptional, (3)
"Beautiful setting. Incredible space well laid out. Owner was very engaging. "
United States
Fred
The price is NZ$399
includes taxes & fees
4 Jan - 5 Jan 2026
Beautiful Loft in the Woods
9.8 out of 10, Exceptional, (8)
"Very clean and property well maintained."
United States
Jessica C.
The price is NZ$277
includes taxes & fees
4 Jan - 5 Jan 2026
Deer Meadow Cabin-Devil's Bathtub/Nat Tunnel, Secluded, Fireplace, Whirlpool Tub
9.8 out of 10, Exceptional, (11)
"Such a beautiful spot with a lot of amenities."
United States
Rhiannon C.
The price is NZ$274
includes taxes & fees
31 Dec - 1 Jan 2026
Secluded cabin on the Clinch river, kayaks & canoes available! Sleeps 6. WIFI.
9.0 out of 10, Wonderful, (2)
"Great spot to explore the area!!"
United States
Joshua T.
The price is NZ$307
includes taxes & fees
4 Jan - 5 Jan 2026
Laurel Lodge Cabin-Secluded, Spacious, Accessible, Devil's Bathtub/Nat Tunnel
10.0 out of 10, Exceptional, (13)
"Very comfortable stay! "
United States
Chasity F.
The price is NZ$210
includes taxes & fees
11 Jan - 12 Jan 2026
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath
9.2 out of 10, Wonderful, (42)
"Great location. Easy walk to town and close to hiking areas. Highly recommend. "
United States
Linda O.
The price is NZ$364
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
10.0 out of 10, Exceptional, (23)
"Very nice and extra clean great time"
United States
Johnny C.
The price is NZ$399
includes taxes & fees
2 Jan - 3 Jan 2026
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
10.0 out of 10, Exceptional, (22)
"Great location with friendly neighbors!"
United States
Evan C.
The price is NZ$515
includes taxes & fees
31 Dec - 1 Jan 2026
Harrogate Home Mountain View’s Dog Friendly
9.6 out of 10, Exceptional, (25)
"This place was just as described and perfect for our stay!"
United States
Melissa M.
The price is NZ$343
includes taxes & fees
4 Jan - 5 Jan 2026
Luxury Brooklyn St APT - Near LMU & Nat’l Park
9.0 out of 10, Wonderful, (2)
"The home was just perfect for what we needed. Looking forward to seeing how it comes out when all construction is finished! Host was very responsive. Will stay again"
United States
Kami L.
The price is NZ$435
includes taxes & fees
21 Jan - 22 Jan 2026
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
10.0 out of 10, Exceptional, (2)
"We stayed here for a wedding weekend in Pineville, KY, and it was absolutely perfect from start to finish. The home was spotless, cozy, and had everything we could possibly need. The beds were so comfortable, and we instantly felt at home the moment we walked in.What truly set this stay apart was the host’s kindness and above-and-beyond hospitality. We got lost in the middle of the night trying to find the property, and the host stayed on the phone with us, patiently guiding us right to the...
United States
Samantha P.
The price is NZ$509
includes taxes & fees
31 Dec - 1 Jan 2026
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
The price is NZ$289
includes taxes & fees
31 Dec - 1 Jan 2026
3-bedroom home away from home in Middesboro. A family friendly environment.
10.0 out of 10, Exceptional, (7)
"Great place that is well stocked and close to amenities as well. Spacious house with an awesome porch with a view!"
United States
Brendan W.
The price is NZ$757
includes taxes & fees
31 Dec - 1 Jan 2026
Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell
9.2 out of 10, Wonderful, (5)
"We enjoyed our stay. "
United States
Emily S.
The price is NZ$640
includes taxes & fees
31 Dec - 1 Jan 2026
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
10.0 out of 10, Exceptional, (1)
"Clean"
United States
Phineas S.
The price is NZ$700
includes taxes & fees
29 Jan - 30 Jan 2026
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU
10.0 out of 10, Exceptional, (1)
"Well cared for property with nice upgrades! Perfect for our stay, everything we needed, and accommodating. "
United States
Hope C.
The price is NZ$382
includes taxes & fees
7 Jan - 8 Jan 2026
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville
The price is NZ$314
includes taxes & fees
31 Dec - 1 Jan 2026
2-bedroom apartment in adorable Pineville with AC for relaxing stays
The price is NZ$776
includes taxes & fees
31 Dec - 1 Jan 2026
Jackson MTN Retreat 3-bedroom entire HOME in Harrogate-Near LMU & Bowling alley
The price is NZ$494
includes taxes & fees
26 Jan - 27 Jan 2026
Welcoming 3-bedroom house with AC in charming Middlesboro

Holiday Home in Pineville

The House on Park Avenue
3.5 star property
The price is NZ$688
includes taxes & fees
31 Dec - 1 Jan 2026
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Harlan County Hotel Reviews

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$274 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