Prestonsburg Vacation Rentals

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Vacation Rentals in Prestonsburg

Our top choices for Prestonsburg vacation rentals

Luxury Estate nestled atop stunning mountaintop golf course!
Interior

Luxury Estate nestled atop stunning mountaintop golf course!

2.0 star property
10.0 out of 10, Exceptional, (6)
"The house is beautiful, and located in the mountains overlooking breathtaking scenery. It is surrounded by a golf course. It is an easy drive to Prestonsburg. Our host was lovely, and checked on us regularly. We really could not have been more pleased. Thank you!"
Luxury Estate nestled atop stunning mountaintop golf course!
Cozy Home in Heart of Prestonsburg
Interior

Cozy Home in Heart of Prestonsburg

10.0 out of 10, Exceptional, (8)
"Great location, quite, adequate"
The price is ￥13,949
￥25,867 total
includes taxes & fees
Sep 29 - Sep 30
Cozy Home in Heart of Prestonsburg
New to the area? Stop by and see the most recent bachelor pad on the scene
Private kitchen

New to the area? Stop by and see the most recent bachelor pad on the scene

2.0 out of 10, (1)
"The place does not exist. Could not find it. Called the host. Host had phone on not accepting calls. I was in the area for my mom's funeral. Had to scramble to find another place to stay. "
New to the area? Stop by and see the most recent bachelor pad on the scene
Near Scenic Parks: Convenient Home in Prestonsburg
House (1 Bedroom) | Interior

Near Scenic Parks: Convenient Home in Prestonsburg

3.0 star property
Near Scenic Parks: Convenient Home in Prestonsburg
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace
Interior

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

9.8 out of 10, Exceptional, (11)
"Excellent service, very friendly"
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace
Appalachian Hideaways
Living area

Appalachian Hideaways

9.0 out of 10, Wonderful, (6)
"Great place "
Appalachian Hideaways
Turkey Creek Retreats
Exterior

Turkey Creek Retreats

10.0 out of 10, Exceptional, (27)
"Would definitely recommend for everyone"
Turkey Creek Retreats
Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails
Outdoor pool

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

9.6 out of 10, Exceptional, (21)
"We really enjoyed our stay. The home was extremely spacious for all of us. The home was extremely clean And Welcoming when you enter. We will Definitely lease this property again on our next trip. "
Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access
Property grounds

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

9.8 out of 10, Exceptional, (6)
"Loved the house had a great experience would definitely stay again"
The price is ￥23,618
￥43,043 total
includes taxes & fees
Sep 30 - Oct 1
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access
Appalachian Hideaways Cabin #2
Microwave, oven, stovetop, dishwasher

Appalachian Hideaways Cabin #2

9.4 out of 10, Exceptional, (10)
"Nice little spot to stay after a day riding the trails."
The price is ￥15,942
￥29,407 total
includes taxes & fees
Sep 26 - Sep 27
Appalachian Hideaways Cabin #2
Cabin in the Appalachian mountains!
Property grounds

Cabin in the Appalachian mountains!

Cabin in the Appalachian mountains!
11 bed 7 bath large home and able to ride right from the home to the HMT trails
Exterior

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

2.0 star property
10.0 out of 10, Exceptional, (1)
11 bed 7 bath large home and able to ride right from the home to the HMT trails
Trail Riders Retreat! Hatfield McCoy Trails. Private Pool. Loads of Parking!
Property grounds

Trail Riders Retreat! Hatfield McCoy Trails. Private Pool. Loads of Parking!

10.0 out of 10, Exceptional, (25)
"Great place to stay very easy trail access don’t even have to go on a main road. Very clean and a quiet place to stay. Would recommend to anyone! "
Trail Riders Retreat! Hatfield McCoy Trails. Private Pool. Loads of Parking!
Suite 3 South Williamson, Ky HMT 10
Exterior

Suite 3 South Williamson, Ky HMT 10

10.0 out of 10, Exceptional, (1)
"Location was great for our needs. Nice accomodations"
The price is ￥18,603
￥36,110 total
includes taxes & fees
Sep 30 - Oct 1
Suite 3 South Williamson, Ky HMT 10
New 3 Bdrm unit w/ great location & ex. amenities
3 bedrooms, desk, iron/ironing board, travel crib

New 3 Bdrm unit w/ great location & ex. amenities

9.6 out of 10, Exceptional, (17)
"This place is exactly as advertised and quieter than expected. Hostess thought of everything. Lovely place for my family of 5. "
New 3 Bdrm unit w/ great location & ex. amenities
Private Cottage Near The Lake with 3 bedrooms, 2 baths, and a gameroom!
Fridge, microwave, oven, stovetop

Private Cottage Near The Lake with 3 bedrooms, 2 baths, and a gameroom!

9.4 out of 10, Exceptional, (3)
"Fully furnished pit stop for your mountain activities....People are very nice...thanks Curtis :-)"
Private Cottage Near The Lake with 3 bedrooms, 2 baths, and a gameroom!
The Nook in Downtown Pikeville
Fridge, microwave, oven, stovetop

The Nook in Downtown Pikeville

9.0 out of 10, Wonderful, (4)
"Small clean apartment like accommodations. Nicer than any hotel room I’ve stayed at in Pikeville and the price was great. "
The Nook in Downtown Pikeville
Country Charm
Fridge, microwave, oven, stovetop

Country Charm

10.0 out of 10, Exceptional, (37)
"Second time staying at the cabin. We had a blast! Awesome place to stay. "
Country Charm
4 Bedroom home less than a mile to Hatfield/McCoy trails
Interior

4 Bedroom home less than a mile to Hatfield/McCoy trails

10.0 out of 10, Exceptional, (32)
"Long weekend trip to the Hatfield and McCoy trails. Perfect place to stay near lots of trails."
4 Bedroom home less than a mile to Hatfield/McCoy trails
The Red Dog Cottage In The Woods w/ Hot Tub
2 bedrooms, free WiFi, bed sheets

The Red Dog Cottage In The Woods w/ Hot Tub

10.0 out of 10, Exceptional, (39)
"This is an amazing place! Such a wonderful idea for rental property. We will be back! Pictures don’t do it justice! "
The Red Dog Cottage In The Woods w/ Hot Tub
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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Top Prestonsburg Hotel Reviews

Brookshire Inn

Brookshire Inn

10/10 Excellent
"Add more breakfast items "
Michael 2-night trip
Posted 6 days ago
Brookshire Inn

Find out more about Prestonsburg

Find out more about Prestonsburg

Search for holiday rentals in Prestonsburg on Expedia! You can easily find your home rentals, villas, holiday apartments in Prestonsburg using one of the methods below:

  • View our selection of featured holiday rentals in Prestonsburg
  • Use the map to find apartments and other holiday homes in the Prestonsburg neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Prestonsburg while they last

Look no further and take a look at our great range of rental properties in Prestonsburg!

Frequently asked questions

Can I find a vacation rental in Prestonsburg?

Yes, we have vacation rentals in Prestonsburg close to East Kentucky Science Center and Planetarium, or you can choose a more secluded option if you're looking for a relaxing stay. Prestonsburg is known for its live music and riverfront. Make sure you have time to check out the entertainment choices and theaters during your trip.

What are some of the best vacation rentals in Prestonsburg?

Luxury Estate nestled atop stunning mountaintop golf course!: Visitors give good reviews to this Prestonsburg vacation home rental, which offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind. Our travelers also rate Cozy Home in Heart of Prestonsburg as a favorite home for rent in Prestonsburg.

How many vacation rentals will I find in Prestonsburg?

Expedia has 3 vacation rentals for your stay in Prestonsburg.

What’s there to see and do in Prestonsburg?

Cultural attractions include Mountain Arts Center and East Kentucky Science Center and Planetarium, whereas Archer Park and Jenny Wiley State Resort Park are a couple of picturesque spots to enjoy the outdoors. StoneCrest Golf Course and Samuel May House are other places to visit while you're in town.

What’s a vacation rental in Prestonsburg like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Prestonsburg. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a small group gathering.