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Holiday Rentals in Harlan County

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Our top choices for Harlan County holiday rentals

Exterior
Beautiful Loft in the Woods

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 €204
includes taxes & fees
28 Dec - 29 Dec
Beautiful Loft in the Woods
Terrace/patio
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath

Holiday Home in Wise

Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath
10.0 out of 10, Exceptional, (13)
"Very comfortable stay! "
United States
Chasity F.
The price is €108
includes taxes & fees
10 Jan - 11 Jan 2026
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath
Exterior
Secluded cabin on the Clinch river, kayaks & canoes available! Sleeps 6. WIFI.

Cabin in Eidson

Secluded cabin on the Clinch river, kayaks & canoes available! Sleeps 6. WIFI.
2.0 star property
9.6 out of 10, Exceptional, (10)
"Such a beautiful spot with a lot of amenities."
United States
Rhiannon C.
The price is €139
includes taxes & fees
31 Dec - 1 Jan 2026
Secluded cabin on the Clinch river, kayaks & canoes available! Sleeps 6. WIFI.
Exterior
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cottage in Cumberland Gap

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
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 €182
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Property grounds
Deer Meadow Cabin-Devil's Bathtub/Nat Tunnel, Secluded, Fireplace, Whirlpool Tub

Cabin in Duffield

Deer Meadow Cabin-Devil's Bathtub/Nat Tunnel, Secluded, Fireplace, Whirlpool Tub
9.8 out of 10, Exceptional, (8)
"Very clean and property well maintained."
United States
Jessica C.
The price is €141
includes taxes & fees
4 Jan - 5 Jan 2026
Deer Meadow Cabin-Devil's Bathtub/Nat Tunnel, Secluded, Fireplace, Whirlpool Tub
Smart TV, fireplace
Laurel Lodge Cabin-Secluded, Spacious, Accessible, Devil's Bathtub/Nat Tunnel

Cabin in DUFFIELD

Laurel Lodge Cabin-Secluded, Spacious, Accessible, Devil's Bathtub/Nat Tunnel
9.0 out of 10, Wonderful, (2)
"Great spot to explore the area!!"
United States
Joshua T.
The price is €157
includes taxes & fees
7 Jan - 8 Jan 2026
Laurel Lodge Cabin-Secluded, Spacious, Accessible, Devil's Bathtub/Nat Tunnel
2 bedrooms, iron/ironing board, free WiFi, bed sheets
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

Holiday Home in Middlesboro

4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
10.0 out of 10, Exceptional, (23)
"Great property! Very clean and homey!"
United States
Lillian I.
The price is €203
includes taxes & fees
28 Dec - 29 Dec
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
Dining
2-bedroom apartment in adorable Pineville with AC for relaxing stays

Apartment in Pineville

2-bedroom apartment in adorable Pineville with AC for relaxing stays
2.0 star property
The price is €159
includes taxes & fees
28 Dec - 29 Dec
2-bedroom apartment in adorable Pineville with AC for relaxing stays
Fridge, microwave, oven, stovetop
Harrogate Home Mountain View’s Dog Friendly

Holiday Home in Harrogate

Harrogate Home Mountain View’s Dog Friendly
10.0 out of 10, Exceptional, (22)
"Great location with friendly neighbors!"
United States
Evan C.
The price is €260
includes taxes & fees
30 Dec - 31 Dec
Harrogate Home Mountain View’s Dog Friendly
Property grounds
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

Holiday Home in Pineville

Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
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 €258
includes taxes & fees
29 Dec - 30 Dec
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Exterior detail
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!

Cottage in Pineville

The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
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 €220
includes taxes & fees
21 Jan - 22 Jan 2026
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!
Fridge, microwave, oven, stovetop
Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell

Holiday Home in Tazewell

Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell
2.0 star property
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 €383
includes taxes & fees
31 Dec - 1 Jan 2026
Tranquil Haven MTN Retreat, 3-bedroom, 2-bath, WIFI, AC in Beautiful Tazewell
3 bedrooms, desk, iron/ironing board, travel cot
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

Holiday Home in Middlesboro

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
9.2 out of 10, Wonderful, (5)
"We enjoyed our stay. "
United States
Emily S.
The price is €324
includes taxes & fees
28 Dec - 29 Dec
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Living area
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville

Holiday Home in Pineville

Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville
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 €234
includes taxes & fees
28 Dec - 29 Dec
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville
Private kitchen
3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre

Holiday Home in Pineville

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."
United States
Stephanie F.
The price is €185
includes taxes & fees
25 Jan - 26 Jan 2026
3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre
Property grounds
Welcoming 3-bedroom house with AC in charming Middlesboro

Holiday Home in Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro
The price is €257
includes taxes & fees
25 Jan - 26 Jan 2026
Welcoming 3-bedroom house with AC in charming Middlesboro
Exterior
Jackson MTN Retreat 3-bedroom entire HOME in Harrogate-Near LMU & Bowling alley

Holiday Home in Harrogate

Jackson MTN Retreat 3-bedroom entire HOME in Harrogate-Near LMU & Bowling alley
2.0 star property
The price is €391
includes taxes & fees
29 Dec - 30 Dec
Jackson MTN Retreat 3-bedroom entire HOME in Harrogate-Near LMU & Bowling alley
Comfort House | Private kitchen
The House on Park Avenue

Holiday Home in Pineville

The House on Park Avenue
3.5 star property
The price is €339
includes taxes & fees
28 Dec - 29 Dec
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

Best Western Of Wise

Best Western Of Wise

10/10 Excellent
"Clean room great staff too!"
Kelsie 1-night trip
Posted 3 days ago
Best Western Of Wise

Find out more about Harlan County

Holiday Homes in Harlan County

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