Photo by Dawn Sanders

Harlan Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Harlan

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)

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)

Beautiful Loft in the Woods

10.0 out of 10, Exceptional, (3)
"Beautiful setting. Incredible space well laid out. Owner was very engaging. "
The price is NZ$395
includes taxes & fees
28 Sept - 29 Sept
Beautiful Loft in the Woods

Harlan, Ky Modern Private Guesthouse 304 Historic Downtown (Vela's Villas)

10.0 out of 10, Exceptional, (1)
"We loved our stay at Vela’s Villa! We had a family gathering and it was wonderful for us to all be together we had a family reunion and it was such a great stay! thanks so much"
Harlan, Ky Modern Private Guesthouse 304 Historic Downtown (Vela's Villas)

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

10.0 out of 10, Exceptional, (14)
"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
29 Sept - 30 Sept
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

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

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! "
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!"
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

"Getaway" to this private beautiful chalet.

9.0 out of 10, Wonderful, (7)
"Very peaceful. Loved the cows."
"Getaway" to this private beautiful chalet.

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. "
The price is NZ$468
includes taxes & fees
28 Sept - 29 Sept
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville

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$448
includes taxes & fees
28 Sept - 29 Sept
Tiny Treehouse Escape with Wi-Fi, Modern Amenities, BBQ Deck + Mountain Views

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.

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
28 Sept - 29 Sept
3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre

Roomy 1896 Victorian Farmhouse Farm Stay in Lee Virginia

10.0 out of 10, Exceptional, (9)
"We enjoyed our stay at the farmhouse. Close enough to Pennington Gap for groceries and restaurants. "
Roomy 1896 Victorian Farmhouse Farm Stay in Lee Virginia

Harrogate Hideaway - 5 Min to LMU & Nat'l Park

9.8 out of 10, Exceptional, (7)
"We enjoyed our stay at this property. It was quiet and met our needs for a two night stay to visit our son in the area."
The price is NZ$334
includes taxes & fees
27 Oct - 28 Oct
Harrogate Hideaway - 5 Min to LMU & Nat'l Park

Welcoming 3-bedroom house with AC in charming Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro
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 Hotel Reviews

Find out more about Harlan

Find out more about Harlan

Everything you need to know about Harlan 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 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Harlan holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Harlan. 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 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 holiday rentals we have selected for you start as low as NZ$334 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Harlan rentals

At Expedia, we put the best Harlan 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 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 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. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Harlan?

Yes, there are holiday rentals close to the most popular sights in Harlan, or you can select a more secluded option if you're looking for a relaxing stay. Harlan is known for its shopping and mountain views. Make sure you have time to check out the lake views and churches during your trip.

What are some of the best holiday rentals that Harlan has to offer?

Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas): This highly rated holiday home rental in Harlan is located in the city centre, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of Access to hot tub in this rental home to help you unwind. Our travellers also rate Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion) as a favourite home for rent in Harlan.

How many holiday rentals are there in Harlan?

Choose from 4 Expedia holiday rentals in Harlan for a memorable holiday.

What can I see and do in Harlan?

Cumberland River and Smith Recreation Area Beach are a couple of lovely local spots to get outside and enjoy nature. Cumberland Gap National Historical Park and Black Mountain Offroad Adventure Area - Putney Trailhead are a couple of places you'll find in the wider area.

What are holiday rentals like in Harlan?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Harlan. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for small groups.