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Leslie County Holiday Rentals

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Top Holiday Rentals Destinations in Leslie County

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

10.0 out of 10, Exceptional, (2)
"Very cute house with everything you need"
Direct Access to Waterfall/Creek Trail of Leatherwood Off Road Park

Historic Property in Hyden KY

10.0 out of 10, Exceptional, (1)
"Had the most peaceful relaxing stay in the mountains. If you can, open the windows and listen to the creek and sleep well."
Historic Property in Hyden KY

Relax and Retreat four bedroom home

2.0 star property
10.0 out of 10, Exceptional, (3)
"Had a great time and the house was located in a great area for what we were going. Very clean and comfortable. Would stay there again for sure"
Relax and Retreat four bedroom home

Small Town Charmer - Rent Entire Home

9.8 out of 10, Exceptional, (58)
"The house was clean and comfortable. The Wi-Fi is fast and it’s a great place to stay while in Hazard for work. "
Small Town Charmer - Rent Entire Home

Red River Gorge/Natural Bridge Cabin Rental

10.0 out of 10, Exceptional, (15)
"The cabin is great Mr Gabbard and his daughter are some of the best people you’ll meet. "
Red River Gorge/Natural Bridge Cabin Rental

Welcome to The Mayor's Retreat! 4-bedroom house in Evarts KY. Book now

10.0 out of 10, Exceptional, (2)
"Cane up from SC to ride Black mountain atv and had a blast definitely will stay here again BJ and his wife are amazing "
Welcome to The Mayor's Retreat! 4-bedroom house in Evarts KY. Book now

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"
The price is NZ$812
includes taxes & fees
10 July - 11 July
The House on Park Avenue-minutes to music venues Laurel Cove and Bell Theater!

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

10.0 out of 10, Exceptional, (1)
"Nice place great for rzr riding "
4BR 2 bath house with full kitchen, living room, hot tub and game room.

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 NZ$1,119
includes taxes & fees
30 June - 1 July
Pine Mountain Inn - Minutes from the Laurel Cove and Bell Theatre music venues!

Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.

9.6 out of 10, Exceptional, (5)
"Perfect little place to hang with the pups and use as a base camp for lots of great hiking in the area. "
Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.

Entire Home near Whitesburg

Entire Home near Whitesburg

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 NZ$395
includes taxes & fees
27 July - 28 July
3-Bedroom Cottage, Peaceful setting, Close to Parks, 2 min. from Bell Theatre

The House on Park Avenue

3.5 star property
The price is NZ$660
includes taxes & fees
10 July - 11 July
The House on Park Avenue

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

8.8 out of 10, Excellent, (3)
"Plenty of space for a family. Adequate furnishings in kitchen to fix meals. I found parking confusing, as the streets are one-way."
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, (2)
"Our family of 4 stayed the first week of June 2025. We absolutely loved our time. We were beyond impressed with the property, especially considering ours was a very last minute booking. The views are amazing and everything within the resort is conveniently located and easy to navigate to. The unit was extremely clean and spacious. Check in was super simple and the host was very responsive. The grounds are immaculately maintained. It’s very family friendly, we only heard the occasional loud...
Harlan, KY GuestHouse 300 Vacation/Weddings/Events (Cole Mansion)

4BR 2 Bath w/ hot tub and game room. Within 10 mins of Harlan & Cumberland.

10.0 out of 10, Exceptional, (1)
"Get cabin and custom service. It was perfect for our group and right next to the trails which was very convenient. Will definitely stay again."
4BR 2 Bath w/ hot tub and game room. Within 10 mins of Harlan & Cumberland.

Manchester's Mountain of Rest

10.0 out of 10, Exceptional, (3)
"We will be back"
Manchester's Mountain of Rest

Secluded Cabin with a mountain view, hot tub, full kitchen, and living room.

10.0 out of 10, Exceptional, (1)
"We can’t wait to return. Everything was great."
Secluded Cabin with a mountain view, hot tub, full kitchen, and living room.

Pappy's Coal Miner's Cabin

10.0 out of 10, Exceptional, (1)
"Only problem I saw was no chlorine tablets in hot tub other than that perfect stay"
Pappy's Coal Miner's Cabin

Beautiful Loft in the Woods

10.0 out of 10, Exceptional, (2)
"Melody was a wonderful and thoughtful host. We had everything we could have wanted or needed including wood for the fire pit. The pictures do not do the property justice. The apartment is gorgeous and very comfortable. The yard was wonderful. We have friends here that we visit at least annually and this will be my go to spot for lodging moving forward. "
The price is NZ$360
includes taxes & fees
29 June - 30 June
Beautiful Loft in the Woods
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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