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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 11 Vacation Homes in Paintsville with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (3)
"This was our second time staying at Bluegrass Palace. This was for our annual staff retreat for Bolts & Quarters Quilt Shop in Parkersburg, West Virginia."
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace
Cozy trail house at the Hatfield McCoy Trails
Aerial view

Cozy trail house at the Hatfield McCoy Trails

10.0 out of 10, Exceptional, (37)
"Came here for a work trip and really enjoyed the home, our crew came to work at a local project and were blessed to stay here rather than a hotel. I can speak for the rest of the crew, we would absolutely stay and vacation here."
Cozy trail house at the Hatfield McCoy Trails
'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!
Exterior detail

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

10.0 out of 10, Exceptional, (22)
"Agree w previous comments about loose dogs on biking trails but dogs didn’t hurt us. Just a bit disconcerting. "
'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!
Near Scenic Parks: Convenient Home in Prestonsburg
Interior

Near Scenic Parks: Convenient Home in Prestonsburg

Near Scenic Parks: Convenient Home in Prestonsburg
Luxury Estate nestled atop stunning mountaintop golf course!
Interior

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!
Hidden Acres Escape: A Bluegrass Retreat
Interior

Hidden Acres Escape: A Bluegrass Retreat

10.0 out of 10, Exceptional, (12)
"This was the perfect place for our family to relax and have fun. The house is beautiful and the views are amazing. We will stay again. "
Hidden Acres Escape: A Bluegrass Retreat
Cozy Home in Heart of Prestonsburg
Interior

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 386
AED 686 total
includes taxes & fees
1 May - 2 May
Cozy Home in Heart of Prestonsburg
Family friendly 12 bed, Serene small town Louisa. Cozy with wifi, AC & farm life
5 bedrooms, iron/ironing board, travel crib, WiFi

Family friendly 12 bed, Serene small town Louisa. Cozy with wifi, AC & farm life

Family friendly 12 bed, Serene small town Louisa. Cozy with wifi, AC & farm life
Creek View Retreat 3 Bedroom- 2 Full Bathroom. Cozy home
Outdoor dining

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
Downtown Paintsville Vacation Rental!
TV, fireplace

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!
Cheerful 3 Bedroom Residential Home
Dining tables

Cheerful 3 Bedroom Residential Home

Cheerful 3 Bedroom Residential Home
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 Paintsville

Downtown Paintsville Vacation Rental!
TV, fireplace

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!
Downtown Paintsville Vacation Rental!
Interior

Downtown Paintsville Vacation Rental!

3.0 star property
Downtown Paintsville Vacation Rental!
Lovely Two Bedroom Rental Unit Free Parking
2 bedrooms, free WiFi, bed sheets

Lovely Two Bedroom Rental Unit Free Parking

Lovely Two Bedroom Rental Unit Free Parking
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.