Book Holiday Homes in Paintsville
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Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Paintsville

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

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

Hidden Acres Escape: A Bluegrass Retreat

Cozy trail house at the Hatfield McCoy Trails

Luxury Estate nestled atop stunning mountaintop golf course!

Cozy Home in Heart of Prestonsburg

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

Near Scenic Parks: Convenient Home in Prestonsburg

Creek View Retreat 3 Bedroom- 2 Full Bathroom. Cozy home
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 |
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Lowest Price | NZ$139 |
Highest Price | NZ$326 |
Popular accommodation | Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace, 'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!, Hidden Acres Escape: A Bluegrass Retreat, Cozy trail house at the Hatfield McCoy Trails, Luxury Estate nestled atop stunning mountaintop golf course!, Cozy Home in Heart of Prestonsburg, Family friendly 12 bed, Serene small town Louisa. Cozy with wifi, AC & farm life, Near Scenic Parks: Convenient Home in Prestonsburg, Creek View Retreat 3 Bedroom- 2 Full Bathroom. Cozy home |
More accommodations in Paintsville
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Ramada Hotel & Conference Center by Wyndham Paintsville

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Downtown Paintsville Vacation Rental!

Downtown Paintsville Vacation Rental!
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^Subject to availability and chosen travel dates.