Book Holiday Homes in Prestonsburg

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Featured Holiday Homes in Prestonsburg

Kentucky's Majestic Mountaintop Estate: The Bluegrass Palace

Kentucky's Majestic Mountaintop Estate: 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: The Bluegrass Palace
Large 4BR Buffalo Mountain Retreat in Williamson with pool,  Ride to trails

Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails

Williamson
Book a stay at this family-friendly vacation home in Williamson. Enjoy private pools, a garden, and a pool table. Popular attractions The Coal House and Williamson ...
Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails
Cozy Home in Heart of Prestonsburg

Cozy Home in Heart of Prestonsburg

Prestonsburg
The price is NZ$341 per night from 1 Jan to 2 Jan
NZ$341
includes taxes & fees
1 Jan - 2 Jan 2025
Stay at this vacation home in Prestonsburg. Enjoy free WiFi, a garden, and patios. Popular attractions Archer Park and Samuel May House are located nearby.
Cozy Home in Heart of Prestonsburg
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💙The Mountain Mama💛 Trail Riders “Home Away From Home”

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

Chattaroy
Stay at this vacation home in Williamson. Enjoy free WiFi, a garden, and patios. Popular attractions Williamson Memorial Fieldhouse and The Coal House are located ...
💙The Mountain Mama💛 Trail Riders “Home Away From Home”
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!
11 bed 7 bath large home and able to ride right from the home to the HMT trails

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

2 out of 5
Williamson
Stay at this vacation home in Williamson. Enjoy air conditioning. Popular attractions The Coal House and Williamson Memorial Fieldhouse are located nearby.
11 bed 7 bath large home and able to ride right from the home to the HMT trails
Turkey Creek Retreats

Turkey Creek Retreats

Belfry
Stay at this vacation home in Belfry. Enjoy free WiFi, a garden, and patios. Popular attractions Williamson Memorial Fieldhouse and The Coal House are located ...
Turkey Creek Retreats
'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 Paintsville ...
'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!
Ryder's Retreat overlooking the city of Williamson!

Ryder's Retreat overlooking the city of Williamson!

Williamson
The price is NZ$506 per night from 24 Dec to 25 Dec
NZ$506
includes taxes & fees
24 Dec - 25 Dec
Stay at this vacation home in Williamson. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions The Coal House and Williamson Memorial ...
Ryder's Retreat overlooking the city of Williamson!
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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.

Prestonsburg 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 Prestonsburg vacation homes are the perfect way for you to wing it.

Holiday houses in Prestonsburg 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 Prestonsburg 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 Prestonsburg adventures, obvs.

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

Prestonsburg Holiday Homes essential information

Accommodation
22 Holiday Homes
Lowest Price
NZ$119
Highest Price
NZ$506
Popular accommodation
Kentucky's Majestic Mountaintop Estate: The Bluegrass Palace, Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails, Cozy Home in Heart of Prestonsburg, 💙The Mountain Mama💛 Trail Riders “Home Away From Home”, 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, Turkey Creek Retreats , 'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!, Ryder's Retreat overlooking the city of Williamson!

Top trending hotels in Prestonsburg

Comfort Suites Prestonsburg West

Comfort Suites Prestonsburg West

2.5 out of 5
51 Hal Rogers Dr, Prestonsburg, KY
Fully refundableReserve now, pay when you stay
The price is NZ$186 per night from 5 Jan to 6 Jan
NZ$186
includes taxes & fees
5 Jan - 6 Jan 2025
Book a stay at this business-friendly hotel in Prestonsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Comfort Suites Prestonsburg West
Super 8 by Wyndham Prestonsburg

Super 8 by Wyndham Prestonsburg

2 out of 5
80 Shoppers Path, Prestonsburg, KY
Fully refundableReserve now, pay when you stay
The price is NZ$119 per night from 5 Jan to 6 Jan
NZ$119
includes taxes & fees
5 Jan - 6 Jan 2025
Book a stay at this business-friendly hotel in Prestonsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Super 8 by Wyndham Prestonsburg
Jenny Wiley State Resort Park

Jenny Wiley State Resort Park

3 out of 5
75 Theatre Ct, Prestonsburg, KY
Stay at this 3-star hotel in Prestonsburg. Enjoy free parking, an outdoor pool, and a marina. Our guests praise the helpful staff and the clean rooms in our ...
Jenny Wiley State Resort Park
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Quality Inn & Suites

Quality Inn & Suites

2.5 out of 5
85 Hal Rogers Drive, Prestonsburg, KY
Fully refundableReserve now, pay when you stay
The price is NZ$169 per night from 5 Jan to 6 Jan
NZ$169
includes taxes & fees
5 Jan - 6 Jan 2025
Book a stay at this business-friendly hotel in Prestonsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Quality Inn & Suites
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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.