Book Holiday Homes in Prestonsburg

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Prestonsburg

Turkey Creek Retreats

Turkey Creek Retreats

Belfry
Stay at this vacation home in Belfry. Enjoy free WiFi, a garden, and patios. Popular attractions Rogers Park and Williamson Memorial Fieldhouse are located ...
Turkey Creek Retreats
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
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access

Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access

Williamson
The price is NZ$447 per night from 28 Apr to 29 Apr
NZ$447
includes taxes & fees
28 Apr - 29 Apr
Stay at this vacation home in Williamson. Enjoy balconies, cable/satellite TV service, and an in-room coffeemaker. Popular attractions South Williamson Park ...
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access
Save an average of 15% on thousands of hotels when you're signed in
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
'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!
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
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 patios and air conditioning. Popular attractions The Coal House and South Williamson Park are located ...
11 bed 7 bath large home and able to ride right from the home to the HMT trails
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
Don't see what you're looking for?
See all available properties in Prestonsburg
View all properties
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
26 Holiday Homes
Lowest Price
NZ$130
Highest Price
NZ$447
Popular accommodation
Turkey Creek Retreats , Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace, Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access, 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!, 11 bed 7 bath large home and able to ride right from the home to the HMT trails, Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails

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$201 per night from 6 Apr to 7 Apr
NZ$201
includes taxes & fees
6 Apr - 7 Apr
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
Quality Inn & Suites Prestonsburg next to Mountain Arts Center

Quality Inn & Suites Prestonsburg next to Mountain Arts Center

2.5 out of 5
85 Hal Rogers Drive, Prestonsburg, KY
Fully refundableReserve now, pay when you stay
The price is NZ$207 per night from 1 Apr to 2 Apr
NZ$207
includes taxes & fees
1 Apr - 2 Apr
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 Prestonsburg next to Mountain Arts Center
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!
Save an average of 15% on thousands of hotels when you're signed in
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$130 per night from 13 Apr to 14 Apr
NZ$130
includes taxes & fees
13 Apr - 14 Apr
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
Don't see what you're looking for?
See all available properties in Prestonsburg
View all properties
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.