Book Holiday Homes in Paintsville

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Featured Holiday Homes in Paintsville

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

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

Langley
Located in Langley, this vacation home is in the mountains, within a 15-minute drive of ARH Our Lady of the Way and McDowell ARH Hospital.
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace
Cozy trail house at the Hatfield McCoy Trails

Cozy trail house at the Hatfield McCoy Trails

Williamson
Located in Williamson, this vacation home is in the mountains, within a 15-minute drive of Williamson Memorial Fieldhouse and The Coal House.
Cozy trail house at the Hatfield McCoy Trails
'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!

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

Hagerhill
Located in Hagerhill, this vacation home is a 4-minute drive from Preston Park and 5 minutes from Fresenius Medical Care.
'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!
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Near Scenic Parks: Convenient Home in Prestonsburg

Near Scenic Parks: Convenient Home in Prestonsburg

Prestonsburg
When you stay at this vacation home in Prestonsburg, you'll be in the mountains, within a 5-minute drive of Samuel May House and Archer Park.
Near Scenic Parks: Convenient Home in Prestonsburg
Luxury Estate nestled atop stunning mountaintop golf course!

Luxury Estate nestled atop stunning mountaintop golf course!

2 out of 5
Prestonsburg
Located in Prestonsburg, this vacation home is a 2-minute drive from StoneCrest Golf Course and 7 minutes from Jenny Wiley State Resort Park.
Luxury Estate nestled atop stunning mountaintop golf course!
Hidden Acres Escape: A Bluegrass Retreat

Hidden Acres Escape: A Bluegrass Retreat

Blaine
With a stay at this vacation home in Blaine, you'll be 15.3 mi (24.7 km) from Eagle Ridge Golf Course and 16 mi (25.7 km) from Paintsville Lake.
Hidden Acres Escape: A Bluegrass Retreat
Cozy Home in Heart of Prestonsburg

Cozy Home in Heart of Prestonsburg

Prestonsburg
The price is AU$313 per night from 7 Apr to 8 Apr
AU$313
includes taxes & fees
7 Apr - 8 Apr
A stay at this vacation home places you in the heart of Prestonsburg, within a 5-minute drive of Samuel May House and Archer Park.
Cozy Home in Heart of Prestonsburg
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

Louisa
Located in Louisa, this vacation home is within a 15-minute drive of The Paveillon and Yatesville Lake State Park.
Family friendly 12 bed, Serene small town Louisa. Cozy with wifi, AC & farm life
Creek View Retreat 3 Bedroom- 2 Full Bathroom.  Cozy home

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

Williamson
With a stay at this vacation home in Williamson, you'll be 10.4 mi (16.7 km) from Moonshine Hill and 11 mi (17.7 km) from Mingo County Public Library.
Creek View Retreat 3 Bedroom- 2 Full Bathroom. Cozy home
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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.

Paintsville Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Paintsville vacation homes are the perfect way for you to wing it.

Holiday houses in Paintsville let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Paintsville in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Paintsville adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Paintsville with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Paintsville vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Paintsville Holiday Homes essential information

Accommodation
11 Holiday Homes
Lowest Price
AU$119
Highest Price
AU$313
Popular accommodation
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace, Cozy trail house at the Hatfield McCoy Trails, 'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!, Near Scenic Parks: Convenient Home in Prestonsburg, Luxury Estate nestled atop stunning mountaintop golf course!, Hidden Acres Escape: A Bluegrass Retreat, Cozy Home in Heart of Prestonsburg, Family friendly 12 bed, Serene small town Louisa. Cozy with wifi, AC & farm life, Creek View Retreat 3 Bedroom- 2 Full Bathroom. Cozy home

Top trending hotels in Paintsville

Ramada Hotel & Conference Center by Wyndham Paintsville

Ramada Hotel & Conference Center by Wyndham Paintsville

2.5 out of 5
624 James Trimble Blvd, Hwy 321 & James Trimble Blvd, Paintsville, KY
Fully refundableReserve now, pay when you stay
The price is AU$202 per night from 13 Apr to 14 Apr
AU$202
includes taxes & fees
13 Apr - 14 Apr
With a stay at Ramada Hotel & Conference Center by Wyndham Paintsville in Paintsville, you'll be within a 5-minute walk of Paintsville ARH Hospital and Fresenius ...
Ramada Hotel & Conference Center by Wyndham Paintsville
Days Inn by Wyndham Paintsville

Days Inn by Wyndham Paintsville

2 out of 5
512 S Mayo Trail, Paintsville, KY
Fully refundableReserve now, pay when you stay
The price is AU$119 per night from 12 Apr to 13 Apr
AU$119
includes taxes & fees
12 Apr - 13 Apr
With a stay at Days Inn by Wyndham Paintsville in Paintsville, you'll be in the mountains, just a 3-minute walk from Preston Park and 10 minutes by foot from ...
Days Inn by Wyndham Paintsville
Downtown Paintsville Vacation Rental!

Downtown Paintsville Vacation Rental!

Paintsville
Located in Paintsville, this vacation home is in a rural location, within a 15-minute walk of Johnson County Public Library and Preston Park.
Downtown Paintsville Vacation Rental!
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Downtown Paintsville Vacation Rental!

Downtown Paintsville Vacation Rental!

3 out of 5
Paintsville
With a stay at this cottage in Paintsville, you'll be within a 10-minute walk of Johnson County Public Library and Preston Park.
Downtown Paintsville Vacation Rental!
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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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^Subject to availability and chosen travel dates.