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Compare 22 Vacation Homes in Prestonsburg with updated reviews, rates, and availability.

Kentucky's Majestic Mountaintop Estate: The Bluegrass Palace

10.0 out of 10, Exceptional, (1)
"Excellent service, very friendly"
Kentucky's Majestic Mountaintop Estate: The Bluegrass Palace

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

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 SAR 394
SAR 723 total
includes taxes & fees
22 Jan - 23 January 2025
Cozy Home in Heart of Prestonsburg

💙The Mountain Mama💛 Trail Riders “Home Away From Home”

10.0 out of 10, Exceptional, (25)
"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”

Luxury Estate nestled atop stunning mountaintop golf course!

2.0 star property
10.0 out of 10, Exceptional, (3)
"Everything was perfect from the booking to checkout. My husband and I live out of state but wanted to host our family and friends. This property exceeded expectations! The home was spacious and decorated beautifully for Christmas. It was both clean and well stocked with supplies. There is also plenty of parking. I highly recommend!"
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

2.0 star property
11 bed 7 bath large home and able to ride right from the home to the HMT trails

Turkey Creek Retreats

10.0 out of 10, Exceptional, (24)
"The location of this home was so conveniently located for us. It was spacious and just what we needed!"
Turkey Creek Retreats

'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!

10.0 out of 10, Exceptional, (17)
"I grew up in the area and come in to visit family. My choices are usually hotels (which are not close) it the lodge at the lake (not convenient). This was the best of both worlds: close to where I needed and PERFECT for a group. We even did the whole family for Thanksgiving here!"
'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!

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 SAR 563
SAR 1,074 total
includes taxes & fees
30 Dec - 31 Dec
Ryder's Retreat overlooking the city of Williamson!

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

Cozy trail house at the Hatfield McCoy Trails

10.0 out of 10, Exceptional, (37)
"Everything was absolutely perfect! The look, the smell, the cleanliness, the mini muffins when we came in, the amount of supplies provided, the option to buy firewood, The accessibility for trailers and SxS's! It was so perfect and comfortable and we will definitely come back again! "
Cozy trail house at the Hatfield McCoy Trails

Creek View Retreat 3 Bedroom- 2 Full Bathroom. Cozy home

9.8 out of 10, Exceptional, (12)
"Great 4 wheeling from this location and a beautiful house. "
Creek View Retreat 3 Bedroom- 2 Full Bathroom. Cozy home

4 Bedroom home less than a mile to Hatfield/McCoy trails

10.0 out of 10, Exceptional, (27)
"This was a great place for me & friends to stay while in the area to ride SXS trails. Great access to Buffalo Mountain Trail and 12 miles to Devil Anse Trail. We did not receive access code & could not get into the home. We were very lucky the basement door was not locked:) "
4 Bedroom home less than a mile to Hatfield/McCoy trails

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!

Country Roads Cliffside Cottage

Country Roads Cliffside Cottage

Big Blue House Apt 1

Big Blue House Apt 1

Cheerful 3 Bedroom Residential Home

Cheerful 3 Bedroom Residential Home

The Bear’s Den

The Bear’s Den

The Nest

The Nest

Near Scenic Parks: Convenient Home in Prestonsburg

Near Scenic Parks: Convenient Home in Prestonsburg
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

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 SAR 394
SAR 723 total
includes taxes & fees
22 Jan - 23 January 2025
Cozy Home in Heart of Prestonsburg

Luxury Estate nestled atop stunning mountaintop golf course!

2.0 star property
10.0 out of 10, Exceptional, (3)
"Everything was perfect from the booking to checkout. My husband and I live out of state but wanted to host our family and friends. This property exceeded expectations! The home was spacious and decorated beautifully for Christmas. It was both clean and well stocked with supplies. There is also plenty of parking. I highly recommend!"
Luxury Estate nestled atop stunning mountaintop golf course!

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
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.