A snow-covered highway curving through a mountainous landscape with a sunset sky. A road sign indicates the direction to Whitesburg and Harlan.

Vacation Homes in Letcher County

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Top Cities in Letcher County

Our top choices for Letcher County vacation homes

1. Red Oak Cottage

Red Oak Cottage
Sassafras
10.0 out of 10, Exceptional, (5 reviews)
"Loved this place "
United States
Partido E.
Red Oak Cottage

2. Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace

Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace
Langley
9.8 out of 10, Exceptional, (25 reviews)
"Really loved our stay! There were a few more bugs than I would have liked, but that is an issue when you are in the mountains.Otherwise the venue was an amazing value for the experience. The host and property manager were very communicative, and the grounds and property were beautiful!"
United States
Gavin C.
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace

3. Whitesburg Vacation Home w/ Glass-Enclosed Porch

Whitesburg Vacation Home w/ Glass-Enclosed Porch
Whitesburg
9.6 out of 10, Exceptional, (15 reviews)
"Wonderful place to stay."
United States
Maria H.
Whitesburg Vacation Home w/ Glass-Enclosed Porch

4. Charming 1-bedroom house in welcoming Big Stone Gap Virginia!

Charming 1-bedroom house in welcoming Big Stone Gap Virginia!
Big Stone Gap
9.8 out of 10, Exceptional, (11 reviews)
"Excellent place to stay"
United States
Michael R.
Charming 1-bedroom house in welcoming Big Stone Gap Virginia!

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

Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)
Harlan
7.6 out of 10, Good, (5 reviews)
"We will rent this property again :)"
United States
David M.
Harlan, KY Modern Private Guesthouse 302 Historic Downtown (Vela's Villas)

6. Rachel’s Retreat Near Leatherwood Off Road Park

Rachel’s Retreat Near Leatherwood Off Road Park
Yeaddiss
10.0 out of 10, Exceptional, (9 reviews)
"Very cute house with everything you need"
United States
Jennifer A.
Rachel’s Retreat Near Leatherwood Off Road Park

7. Small Town Charmer - Hazards Best Airbnb!

Small Town Charmer - Hazards Best Airbnb!
Hazard
10.0 out of 10, Exceptional, (69 reviews)
"Beautiful home, very clean and conveniently located to our family. We would definitely stay here again "
United States
Sue B.
Small Town Charmer - Hazards Best Airbnb!

8. Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath

Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath
Wise
10.0 out of 10, Exceptional, (14 reviews)
"Very comfortable stay! "
United States
Chasity F.
The price is AED 459
AED 560 total
includes taxes & fees
13 Nov - 14 Nov
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath

9. Family farm guest house 10 minutes from Big Stone

Family farm guest house 10 minutes from Big Stone
Dryden
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful accommodation! Clean, great lighting, nicely decorated, well-stocked, modern kitchen."
United States
John T.
Family farm guest house 10 minutes from Big Stone

10. Vicco Cottage Between Hazard and Whitesburg

Vicco Cottage Between Hazard and Whitesburg
Vicco
10.0 out of 10, Exceptional, (2 reviews)
"The house is cute as a button, pet friendly and very clean. Everything you need for your stay is available and the Host is very good at communicating with any issues or questions you may have."
United States
Susan L.
Vicco Cottage Between Hazard and Whitesburg

11. Big Tree Lodge- Near Leatherwood Off Road Park!

Big Tree Lodge- Near Leatherwood Off Road Park!
Slemp
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay at Big Tree Lodge and it was a great place for our group to spend time together and enjoy our stay. Our host, and we appreciate the opportunity to stay at the property. We would recommend Big Tree Lodge to others looking for a place to stay."
United States
Garry N.
Big Tree Lodge- Near Leatherwood Off Road Park!

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

Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.
Partridge
9.8 out of 10, Exceptional, (16 reviews)
"Best stay we have had in the area. Wonderful place. Will stay here again!!!"
United States
Darren
The price is AED 514
AED 615 total
includes taxes & fees
3 Dec - 4 Dec
Bed and Biscuit Inn Pet friendly ! Near Kingdom come park & Pine mtn.

13. 1-bedroom Little Lodge 2.5 miles from Hillbilly Trails

1-bedroom Little Lodge 2.5 miles from Hillbilly Trails
Jenkins
10.0 out of 10, Exceptional, (2 reviews)
"Very cute little place to stay and super clean. The check in process was very easy! The host was very friendly and quick to respond!"
United States
Keira L.
1-bedroom Little Lodge 2.5 miles from Hillbilly Trails

14. 360 Degree Mountain View

360 Degree Mountain View
Jenkins
9.8 out of 10, Exceptional, (8 reviews)
"Thank you we had an amazing weekend and everything was perfect ! Will most definitely book again"
United States
Crystal E.
360 Degree Mountain View

15. Laptop-Friendly Appalachian Mountain Retreat!

Laptop-Friendly Appalachian Mountain Retreat!
Norton
10.0 out of 10, Exceptional, (15 reviews)
"We had a great stay at this property while visiting family for July 4th! The home is clean, beautiful, and well-appointed. Highly recommended!"
United States
Jen S.
Laptop-Friendly Appalachian Mountain Retreat!

16. Wayne's World - A Nature Lovers Dream!

Wayne's World - A Nature Lovers Dream!
Hazard
10.0 out of 10, Exceptional, (4 reviews)
"Great place!"
United States
Eric K.
Wayne's World - A Nature Lovers Dream!

17. Handicapped Friendly House in the peaceful country side

Handicapped Friendly House in the peaceful country side
Jonesville
10.0 out of 10, Exceptional, (32 reviews)
"Beautiful property and home. The check in and out process was seamless and the host was very attentive making sure we had everything we need."
United States
Dee L.
Handicapped Friendly House in the peaceful country side

18. Spacious 5-bedroom house in town-within walking distance to everything

Spacious 5-bedroom house in town-within walking distance to everything
Clintwood
9.0 out of 10, Wonderful, (2 reviews)
"We really enjoyed our stay here. Melinda was amazing. Quick to respond to any questions I had. The location was perfect as we were attending a graduation in Wise. Home was clean and large enough for my family. Fully stocked with linens, beds were very comfortable, kitchen had everything we needed. A bonus was the coffee shop right next store. If we ever pass through this area again we would definitely stay here. "
United States
Cheryl
The price is AED 393
AED 834 total
includes taxes & fees
16 Nov - 17 Nov
Spacious 5-bedroom house in town-within walking distance to everything

19. Valley View Retreat Near Whitesburg KY

Valley View Retreat Near Whitesburg KY
Whitesburg
7.0 out of 10, Good, (2 reviews)
"The house is spacious and the beds are good. The AC works well. Mostly untouched circa 1960. The single bath room is tiny and lighting through out the house is inadequate. Nice neighborhood."
United States
Robert B.
Valley View Retreat Near Whitesburg KY

20. Breaks Home: 3 Mi to ATV Trails!

Breaks Home: 3 Mi to ATV Trails!
Breaks
10.0 out of 10, Exceptional, (7 reviews)
"Loved this place. Its very well appointed and my kids enjoyed playing in the creek. My favorite was the front porch. Very comfortable and the property managers were very responsive."
United States
Leah G.
Breaks Home: 3 Mi to ATV Trails!
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 Letcher County Hotel Reviews

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