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Compare 19 Vacation Homes in Prestonsburg with updated reviews, rates, and availability.

Turkey Creek Retreats
Living room offers a full size hideaway bed and fireplace.
Turkey Creek Retreats
10.0 out of 10, Exceptional, (23)
"The location of this home was so conveniently located for us. It was spacious and just what we needed!"
Turkey Creek Retreats
Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails
Exterior
Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails
9.6 out of 10, Exceptional, (19)
"We had a great time. The house is beautiful and very spacious. Location is perfect because it’s close to everything. Neighbors were very nice! Host was super nice and very accommodating. We will definitely come back and stay again! Dirt Days was a lot of fun for us and my nephews. The vendors were very friendly. The town has a lot of cool history."
Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails
Cozy Home in Heart of Prestonsburg
Living area
Cozy Home in Heart of Prestonsburg
10.0 out of 10, Exceptional, (6)
"Stopped in the area to visit family that has passed on and to find our family cemetery. Was unable to find the cemetery but still enjoyed my trip. We also visted Loretta Lynns place."
The price is AED 529
AED 882 total
includes taxes & fees
12 Nov - 13 Nov
Cozy Home in Heart of Prestonsburg
Luxury Estate nestled atop stunning mountaintop golf course!
Front view from circular drive.
Luxury Estate nestled atop stunning mountaintop golf course!
2.0 star property
10.0 out of 10, Exceptional, (1)
"We were coming to town to celebrate my son's wedding and we needed a big house. Not easy to find in this area. This house fit the bill and was simply AMAZING! The house is easily the best house that we have ever stayed at...hands down! Plenty of rooms and everything you could ever need to play, cook, and relax with family and friends. I could not more highly recommend this house. We LOVED it!!! John"
Luxury Estate nestled atop stunning mountaintop golf course!
11 bed 7 bath large home and able to ride right from the home to the HMT trails
Exterior
11 bed 7 bath large home and able to ride right from the home to the HMT trails
2.0 star property
11 bed 7 bath large home and able to ride right from the home to the HMT trails
'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!
Hagerhill Vacation Rental | 3BR | 2BA | 5 Entry Steps | 4,100 Sq Ft
'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!
10.0 out of 10, Exceptional, (16)
"Lovely home that easily accommodated our little family gathering. Perfect place for us to be together after 6 long years!"
'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!
Ryder's Retreat overlooking the city of Williamson!
Exterior
Ryder's Retreat overlooking the city of Williamson!
8.8 out of 10, Excellent, (5)
"The owner was very quick at responding, and willing to alleviate any concerns immediately. The property was very clean and well taken care of. The inside had many cosmetic upgrades. There were a few minor broken things (toilet paper holder broketoilet lidtttoilet lid"
The price is AED 1,098
AED 1,725 total
includes taxes & fees
11 Nov - 12 Nov
Ryder's Retreat overlooking the city of Williamson!
4 bedroom Trail House in Williamson, WV
Exterior of house
4 bedroom Trail House in Williamson, WV
9.8 out of 10, Exceptional, (37)
"We highly recommend (group of 8) We stayed right after Hurricane Helene had passed through the area. Our home owner made sure we had everything we needed to make due while the communtity dealt with a few power and water issues. She went above and beyond to make sure we weeetaken carw of. "
4 bedroom Trail House in Williamson, WV
💙The Mountain Mama💛 Trail Riders “Home Away From Home”
Exterior
💙The Mountain Mama💛 Trail Riders “Home Away From Home”
10.0 out of 10, Exceptional, (24)
"Beautiful home. Tons of room. Beds everywhere. Didnt see in the add that it had a pool table in the basement! "
💙The Mountain Mama💛 Trail Riders “Home Away From Home”
Cozy trail house at the Hatfield McCoy Trails
Exterior
Cozy trail house at the Hatfield McCoy Trails
10.0 out of 10, Exceptional, (35)
"This was family trip to ride the trails. House was great location. Easy access to trails and town yet private. Our host Daniel made sure everything met our expectations. Highly recommend staying here!"
Cozy trail house at the Hatfield McCoy Trails
Creek View Retreat 3 Bedroom- 2 Full Bathroom. Cozy home
Exterior
Creek View Retreat 3 Bedroom- 2 Full Bathroom. Cozy home
9.8 out of 10, Exceptional, (11)
"We enjoyed our stay. The house is very clean and comfortable. "
Creek View Retreat 3 Bedroom- 2 Full Bathroom. Cozy home
4 Bedroom home less than a mile to Hatfield/McCoy trails
Exterior of The Gibson House
4 Bedroom home less than a mile to Hatfield/McCoy trails
10.0 out of 10, Exceptional, (26)
"Was a super nice clean place we enjoyed the outdoor pavilion and fire pit. The reason for the 4stars on the location is we had 22’ trailers and it was tough getting them up the hill. A single trailer would have been a breeze. Ashley replied super quickly on any txt I sent her. "
4 Bedroom home less than a mile to Hatfield/McCoy trails
Downtown Paintsville Vacation Rental!
Paintsville Vacation Rental | 1,500 Sq Ft | 3BR | 2BA | Stairs Required
Downtown Paintsville Vacation Rental!
8.0 out of 10, Very Good, (2)
"The home and linens were clean, plenty of living space. The house is like walking into a time capsule of your grandmothers home. Very small bathrooms, drafty window AC units still installed in late November, old TVs. No grill outside was disappointing. Tight single stacked parking. There is another small house on the same lot with multiple vehicles coming and going, combined with the close neighbors and there is limited privacy and no outdoor space."
Downtown Paintsville Vacation Rental!
Kentucky's Majestic Mountaintop Estate: The Bluegrass Palace
Exterior
Kentucky's Majestic Mountaintop Estate: The Bluegrass Palace
Kentucky's Majestic Mountaintop Estate: The Bluegrass Palace
Country Roads Cliffside Cottage
Living area
Country Roads Cliffside Cottage
Country Roads Cliffside Cottage
Big Blue House Apt 1
Exterior
Big Blue House Apt 1
Big Blue House Apt 1
Cheerful 3 Bedroom Residential Home
Exterior
Cheerful 3 Bedroom Residential Home
Cheerful 3 Bedroom Residential Home
The Bear’s Den
Exterior
The Bear’s Den
The Bear’s Den
The Nest
Exterior
The Nest
The Nest
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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Other property types in Prestonsburg

Cozy Home in Heart of Prestonsburg
Living area
Cozy Home in Heart of Prestonsburg
10.0 out of 10, Exceptional, (6)
"Stopped in the area to visit family that has passed on and to find our family cemetery. Was unable to find the cemetery but still enjoyed my trip. We also visted Loretta Lynns place."
The price is AED 529
AED 882 total
includes taxes & fees
12 Nov - 13 Nov
Cozy Home in Heart of Prestonsburg
New to the area? Stop by and see the most recent bachelor pad on the scene
Room
New to the area? Stop by and see the most recent bachelor pad on the scene
2.0 out of 10, (1)
"The place does not exist. Could not find it. Called the host. Host had phone on not accepting calls. I was in the area for my mom's funeral. Had to scramble to find another place to stay. "
New to the area? Stop by and see the most recent bachelor pad on the scene
Luxury Estate nestled atop stunning mountaintop golf course!
Front view from circular drive.
Luxury Estate nestled atop stunning mountaintop golf course!
2.0 star property
10.0 out of 10, Exceptional, (1)
"We were coming to town to celebrate my son's wedding and we needed a big house. Not easy to find in this area. This house fit the bill and was simply AMAZING! The house is easily the best house that we have ever stayed at...hands down! Plenty of rooms and everything you could ever need to play, cook, and relax with family and friends. I could not more highly recommend this house. We LOVED it!!! John"
Luxury Estate nestled atop stunning mountaintop golf course!
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.