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Harlan Holiday Rentals

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Check prices for these dates

Tonight
29 Sept - 30 Sept
Tomorrow
30 Sept - 1 Oct
This weekend
3 Oct - 5 Oct
Next weekend
10 Oct - 12 Oct

Holiday Rentals in Harlan

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

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)
Exterior

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
Exterior

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 HK$856
HK$1,775 total
includes taxes & fees
30 Sept - 1 Oct
Beautiful Loft in the Woods
Harlan, Ky Modern Private Guesthouse 304 Historic Downtown (Vela's Villas)
Exterior detail

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,
2 bedrooms, iron/ironing board, free WiFi, bed sheets

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

10.0 out of 10, Exceptional, (16)
"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 HK$926
HK$1,621 total
includes taxes & fees
30 Sept - 1 Oct
4.6 miles from LMU. Cozy 2-bedroom Lustron home located in Middlesboro, Ky,
1928 Home in the heart of Cumberland Gap
Exterior

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
Terrace/patio

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
Blissful Bungalow across from LMU campus
Fridge, microwave, oven, stovetop

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
Welcoming 3-bedroom house with AC in charming Middlesboro
Terrace/patio

Welcoming 3-bedroom house with AC in charming Middlesboro

Welcoming 3-bedroom house with AC in charming Middlesboro
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Property grounds

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

10.0 out of 10, Exceptional, (1)
The price is HK$637
HK$1,534 total
includes taxes & fees
1 Oct - 2 Oct
Charming 3-bedroom house with WiFi, AC in Pineville Kentucky
Harrogate Home Mountain View’s Dog Friendly
Fridge, microwave, oven, stovetop

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 HK$756
HK$1,713 total
includes taxes & fees
1 Oct - 2 Oct
Harrogate Home Mountain View’s Dog Friendly
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit · Hiking Trails
Pool

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

9.2 out of 10, Wonderful, (24)
"Everything was good!"
The price is HK$972
HK$1,828 total
includes taxes & fees
30 Sept - 1 Oct
Posh Mountain Camping w/ 120" Screen Theater ·Hot-Tub · Firepit · Hiking Trails
Cozy log cabin near Pennington Gap and Jonesville, VA known as "The Duck Pond"
1 bedroom, bed sheets

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

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
Private kitchen

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 HK$537
HK$1,621 total
includes taxes & fees
7 Oct - 8 Oct
3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre
Roomy 1896 Victorian Farmhouse Farm Stay in Lee Virginia
Exterior

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
The House on Park Avenue
Private kitchen

The House on Park Avenue

3.5 star property
The price is HK$2,262
HK$3,108 total
includes taxes & fees
30 Sept - 1 Oct
The House on Park Avenue
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
3 bedrooms, desk, iron/ironing board, travel cot

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

9.2 out of 10, Wonderful, (5)
"We enjoyed our stay. "
The price is HK$1,642
HK$3,233 total
includes taxes & fees
29 Oct - 30 Oct
Charming 3-bedroom house in the Crater City near State Parks, LMU, & hospitals.
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
Exterior

Cozy Cumberland Gap Cottage Near LMU & Nat’l Park

9.2 out of 10, Wonderful, (39)
"Just as advertised. Very quiet and enjoyable stay!"
The price is HK$770
HK$1,636 total
includes taxes & fees
2 Oct - 3 Oct
Cozy Cumberland Gap Cottage Near LMU & Nat’l Park
"Getaway" to this private beautiful chalet.
Terrace/patio

"Getaway" to this private beautiful chalet.

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

Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

10/10 Excellent
"Clean room Great breakfast Staff friendly and helpful "
Tammy 1-night trip
Posted 18 hours ago
Holiday Inn Express Middlesboro by IHG

Find out more about Harlan

Find out more about Harlan

Search for holiday rentals in Harlan on Expedia! You can easily find your home rentals, villas, holiday apartments in Harlan using one of the methods below:

  • View our selection of featured holiday rentals in Harlan
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  • Enter your travel dates to view the best deals on holiday rentals in Harlan while they last

Look no further and take a look at our great range of rental properties in Harlan!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.