Photo by Dawn Sanders

Harlan Holiday Rentals

    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

Holiday Rentals in Harlan

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

9.4 out of 10, Exceptional, (23)
"This was the perfect place for a long weekend getaway. The host communicated well and checked in via message to ensure everything was running smoothly. Very cute camper and surprisingly comfy beds - overall a wonderful experience. Thanks!"
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit · Hiking Trails

A beautiful colonial house with breathtaking views of the Cumberland Gap Mnts!

8.8 out of 10, Excellent, (25)
"Stayed for LMU graduation. Great location and great property, very accommodating hosts. Thank you!"
The price is AU$934
includes taxes & fees
19 July - 20 July
A beautiful colonial house with breathtaking views of the Cumberland Gap Mnts!

Harrogate Home Mountain View’s Dog Friendly

9.8 out of 10, Exceptional, (19)
"The entire stay was great. The house was nice and cozy, the beds were comfortable and the showers were great. Overall a very comfortable stay. Great hosts."
The price is AU$461
includes taxes & fees
16 July - 17 July
Harrogate Home Mountain View’s Dog Friendly

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

10.0 out of 10, Exceptional, (1)
The price is AU$402
includes taxes & fees
16 July - 17 July
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky

1928 Home in the heart of Cumberland Gap

9.8 out of 10, Exceptional, (86)
"Nice spot that is conveniently located in Cumberland Gap. Highly recommend!!!"
The price is AU$353
includes taxes & fees
14 July - 15 July
1928 Home in the heart of Cumberland Gap

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

4.0 out of 10, (2)
"The inside photos are somewhat representative of the interior. This is not a “peaceful” location. There were rowdy teens and basketball games very late. Also, you are literally right beside the highway so expect traffic noise. I could deal with all of this, but the smell. I have never left an accommodation nor have I ever left a negative review. However, I must warn others that the smell of tobacco smoke in this place was unlike anything I’ve ever experienced. I went and bought a candle hoping...
The price is AU$347
includes taxes & fees
21 July - 22 July
3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre

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 AU$367
includes taxes & fees
11 Aug - 12 Aug
Charming 2-bedroom bungalow with AC, WiFi in pleasant Pineville

Pine Mountain Inn - Minutes from the Laurel Cove and Bell Theatre music venues!

10.0 out of 10, Exceptional, (2)
"Perfect for our event! Very laid back atmosphere. "
The price is AU$883
includes taxes & fees
7 Aug - 8 Aug
Pine Mountain Inn - Minutes from the Laurel Cove and Bell Theatre music venues!

The House on Park Avenue

3.5 star property
The price is AU$607
includes taxes & fees
14 July - 15 July
The House on Park Avenue

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

10.0 out of 10, Exceptional, (7)
"Perfect! Owner was awesome and incredibly responsive. The house was immaculate and ideal for us. Wish we could have enjoyed the fire pit too but we were able to stay high and dry and cozy in the house and avoid the torrential downpours. There is even a nice covered area to get to the carport from the house. Neat historical home close to everything and we were honored to be the first VRBO customer. Thank you for a great experience. We will be back!"
The price is AU$327
includes taxes & fees
14 July - 15 July
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,

Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

9.0 out of 10, Wonderful, (4)
"We enjoyed our stay. "
The price is AU$517
includes taxes & fees
3 Aug - 4 Aug
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.

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

The price is AU$784
includes taxes & fees
12 Aug - 13 Aug
Spacious Renovated Ranch Retreat near Tackett Creek & Cumberland Gap Park, & LMU

5 minutes from LMU!

9.8 out of 10, Exceptional, (6)
"Have stayed here several times. Always a great stay. Place is clean and tidy and owner is always responsive to my needs. Will definitely stay here again!"
The price is AU$498
includes taxes & fees
3 Aug - 4 Aug
5 minutes from LMU!
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

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 GuestHouse 300 Vacation/Weddings/Events (Cole Mansion): This highly rated holiday home rental in Harlan is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

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 Gap National Historical Park and Cumberland River are a couple of lovely local spots to get outside and enjoy nature. Smith Recreation Area Beach 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.