Harlan County Vacation Rentals

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Harlan County Vacation Rentals

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

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

Putney KY
Guests staying at this cabin enjoy a hot tub, laundry facilities, and barbecue grills.
Hot Tub
Kitchen
Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion)

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

Harlan KY
Guests of this vacation home enjoy access to a water park, laundry facilities, and barbecue grills. This smoke-free vacation home also has a garden.
Kitchen
Washer
Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)

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

Harlan KY
Guests staying at this vacation home enjoy a hot tub, laundry facilities, and a garden. This smoke-free vacation home also has barbecue grills.
Hot Tub
Kitchen
Beautiful Loft in the Woods

Beautiful Loft in the Woods

Harlan KY
$212 nightly
The price is $234 total per night
$234 total
Dec 21 - Dec 22
Total with taxes and fees
This apartment is a smoke-free apartment building.
Kitchen
Pet friendly
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit · Hiking Trails

Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit · Hiking Trails

Jonesville VA
Guests staying at Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit · Hiking Trails enjoy a hot tub, local meal delivery service, and barbecue grills. Transportation is made easy with limo/town car service.
Hot Tub
Kitchen
Direct Access to Waterfall/Creek Trail of Leatherwood Off Road Park

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

Yeaddiss KY
At this vacation home, guests have access to features like laundry facilities.
Kitchen
Washer
Cozy log cabin near Pennington Gap and Jonesville, VA known as "The Duck Pond"

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

2 out of 5
Pennington Gap VA
This cabin is a smoke-free cabin.
Pet friendly
Air conditioning
Whitesburg Vacation Home w/ Screened Porch

Whitesburg Vacation Home w/ Screened Porch

3 out of 5
Whitesburg KY
This cottage features free WiFi in public areas and barbecue grills. A stay here includes free offsite parking.
Kitchen
Washer
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!

The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!

Pineville KY
$282 nightly
The price is $311 total per night
$311 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Guests staying at this cottage enjoy a hot tub, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.
Hot Tub
Kitchen
Mountain Views - LMU 1 1/2

Mountain Views - LMU 1 1/2

2 out of 5
Harrogate TN
At this apartment, guests have access to features like laundry facilities.
Kitchen
Washer
Blissful Bungalow across from LMU campus

Blissful Bungalow across from LMU campus

Harrogate TN
At this vacation home, guests have access to features like laundry facilities.
Kitchen
Washer
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

Cumberland Gap TN
$190 nightly
The price is $212 total per night
$212 total
Dec 21 - Dec 22
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.
Kitchen
Washer
1928 Home in the heart of Cumberland Gap

1928 Home in the heart of Cumberland Gap

Cumberland Gap TN
At this vacation home, guests have access to a garden.
Kitchen
Pet friendly
Cozy Cottage-Devil's Bathtub/Nat Tunnel-Secluded, WiFi, Fireplace, Whirlpool Tub

Cozy Cottage-Devil's Bathtub/Nat Tunnel-Secluded, WiFi, Fireplace, Whirlpool Tub

Duffield VA
$141 nightly
The price is $155 total per night
$155 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has barbecue grills.
Kitchen
Washer
Laurel Lodge Cabin-Secluded, Spacious, Accessible, Devil's Bathtub/Nat Tunnel

Laurel Lodge Cabin-Secluded, Spacious, Accessible, Devil's Bathtub/Nat Tunnel

DUFFIELD VA
$162 nightly
The price is $178 total per night
$178 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has barbecue grills.
Kitchen
Air conditioning
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU

Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU

Middlesboro KY
$535 nightly
The price is $590 total per night
$590 total
Dec 21 - Dec 22
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities.
Washer
Dryer
Welcoming 3-bedroom house with AC in charming Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro

Middlesboro KY
At this vacation home, guests have access to features like laundry facilities. This vacation home also has barbecue grills.
Washer
Dryer
Secluded cabin on the Clinch river, kayaks & canoes available! Sleeps 6. WIFI.

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

2 out of 5
Eidson TN
$144 nightly
The price is $159 total per night
$159 total
Dec 31 - Jan 1, 2026
Total with taxes and fees
At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has barbecue grills.
Kitchen
Washer
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See all available properties in Harlan County
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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.

Hotel Options in Harlan County

    Quality Inn

    Quality Inn

    2608 South Highway 421 Harlan KY
    $89 nightly
    The price is $101 total per night from Jan 4 to Jan 5
    $101 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    8.4/10 Very Good! (339 reviews)
    Rodeway Inn

    Rodeway Inn

    355 Skidmore Drive Harlan KY
    $51 nightly
    The price is $58 total per night from Dec 28 to Dec 29
    $58 total
    Dec 28 - Dec 29
    Total with taxes and fees
    5.6/10 (231 reviews)
    The Inn at Wise

    The Inn at Wise

    110 E Main Street Wise VA
    $109 nightly
    The price is $122 total per night from Dec 21 to Dec 22
    $122 total
    Dec 21 - Dec 22
    Total with taxes and fees
    9.2/10 Wonderful! (1,001 reviews)

Orbitz makes it easy to find vacation rentals in Harlan County 

🏠 What is the best price for a Harlan County vacation rental?


Harlan County rentals range between $58 and $590 per night. At Orbitz, we have a vacation rental for every budget.


🏠 What types of vacation rentals in Harlan County can I rent?


Choose from apartments to beautifully decorated vacation homes, condo resorts or even B&Bs or motels for your next Harlan County getaway. Orbitz filters your search results so you can find the best Harlan County vacation rental for you. We have tons of options.


🏠 Are cancellations free on Harlan County vacation rentals with Orbitz?


You may be able to cancel or amend your Harlan County vacation rental booking free of charge before a pre-agreed deadline. Make sure to check the terms of cancellation before you book—so you know exactly where you stand. 


🏠 How do I find the best vacation rental deals in Harlan County?


Enter your travel dates, and we’ll do the rest. You can then browse our exciting deals and all the tempting vacation rentals we have on offer in Harlan County by filtering your search by amenities, prices, and property types and look at customers ratings to help you pick.


🏠 How do I cancel my vacation rental booking through Orbitz


Vacation rentals have slightly different rules to other bookings on Orbitz. Usually, you need to contact your property manager, you may be able to get a full refund before the cancellation date. Click My TripsOpens in a new window on your Orbitz account page to find the right information contact. If you need more help, visit our Customer ServiceOpens in a new window page. 


🏠 What are the advantages of booking a vacation rental in Harlan County?


When you book a Harlan County vacation rental, you have the privacy of home and can add on those luxury amenities of a hotel. Filter your vacation rental results to find a place with a hot tub or pool, games rooms or large patio with a barbecue. With so much choice on offer, it’s easy to plan the perfect trip with Orbitz. 


🏠 Where can I find vacation rentals in Harlan County?


Escape back to nature and check out some of the smaller towns. You’ll find great vacation rentals right across Harlan County—with plenty of hidden gems. We also have plenty of inventory in Harlan County main cities and near popular attraction spots.


🏠 Why should I book my Harlan County vacation rental with Orbitz?


At Orbitz, we search the market for the best accommodation, flights, and car rental deals, so you don’t have to. We’ll help you build your dream Harlan County vacation. With plenty of vacation rentals on offer, you can be sure to find the one that’s right for you in just a few clicks. 


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