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
Book a stay at this family-friendly vacation home in Langley. Enjoy free WiFi, private pools, and a garden.
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace
'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!

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

Hagerhill
Book a stay at this family-friendly vacation home in Hagerhill. Enjoy a garden, furnished patios, and in-room washers/dryers. Popular attractions Preston Park ...
'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!
Hidden Acres Escape: A Bluegrass Retreat

Hidden Acres Escape: A Bluegrass Retreat

Blaine
Book a stay at this family-friendly vacation home in Blaine. Enjoy free WiFi, private pools, and a garden.
Hidden Acres Escape: A Bluegrass Retreat
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Cozy trail house at the Hatfield McCoy Trails

Cozy trail house at the Hatfield McCoy Trails

Williamson
Stay at this vacation home in Williamson. Enjoy free WiFi, a garden, and patios. Popular attractions Williamson Memorial Fieldhouse and Rogers Park are located ...
Cozy trail house at the Hatfield McCoy Trails
Luxury Estate nestled atop stunning mountaintop golf course!

Luxury Estate nestled atop stunning mountaintop golf course!

2 out of 5
Prestonsburg
Stay at this vacation home in Prestonsburg. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions StoneCrest Golf Course and Jenny Wiley ...
Luxury Estate nestled atop stunning mountaintop golf course!
Cozy Home in Heart of Prestonsburg

Cozy Home in Heart of Prestonsburg

Prestonsburg
The price is NZ$326 per night from 19 Mar to 20 Mar
NZ$326
includes taxes & fees
19 Mar - 20 Mar
Stay at this vacation home in Prestonsburg. Enjoy free WiFi, a garden, and patios. Popular attractions Samuel May House and Mountain Arts Center are located ...
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
Stay at this vacation home in Louisa. Enjoy an in-room coffeemaker and air conditioning. Popular attractions The Paveillon and Eagle Ridge Golf Course are located ...
Family friendly 12 bed, Serene small town Louisa. Cozy with wifi, AC & farm life
Near Scenic Parks: Convenient Home in Prestonsburg

Near Scenic Parks: Convenient Home in Prestonsburg

Prestonsburg
Stay at this vacation home in Prestonsburg. Enjoy cable/satellite TV service, an in-room coffeemaker, and air conditioning. Popular attractions Samuel May House ...
Near Scenic Parks: Convenient Home in Prestonsburg
Creek View Retreat 3 Bedroom- 2 Full Bathroom.  Cozy home

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

Williamson
Stay at this vacation home in Williamson. Enjoy free WiFi, cable/satellite TV service, and air conditioning. Popular attractions Laurel Lake Wildlife Management ...
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
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

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 NZ$212 per night from 6 Apr to 7 Apr
NZ$212
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this business-friendly hotel in Paintsville. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. ...
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 NZ$139 per night from 16 Mar to 17 Mar
NZ$139
includes taxes & fees
16 Mar - 17 Mar
Book a stay at this business-friendly motel in Paintsville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Days Inn by Wyndham Paintsville
Downtown Paintsville Vacation Rental!

Downtown Paintsville Vacation Rental!

Paintsville
Stay at this vacation home in Paintsville. Enjoy cable/satellite TV service, in-room washers/dryers, and in-room fireplaces. Popular attractions Johnson County ...
Downtown Paintsville Vacation Rental!
Save an average of 15% on thousands of hotels when you're signed in
Downtown Paintsville Vacation Rental!

Downtown Paintsville Vacation Rental!

3 out of 5
Paintsville
Stay at this 3-star cottage in Paintsville. Enjoy free parking, in-room fireplaces, and air conditioning. Popular attractions Johnson County Public Library and ...
Downtown Paintsville Vacation Rental!
Don't see what you're looking for?
See all available properties in Paintsville
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.