Prestonsburg Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Prestonsburg vacation rentals

Interior
Cozy Home in Heart of Prestonsburg

Vacation Home in Prestonsburg

Cozy Home in Heart of Prestonsburg
9.8 out of 10, Exceptional, (9)
"We loved our stay at The Shotgun House! It was very clean, peaceful and safe. The bed was super comfortable, and we lacked for nothing as the host has the place fully stocked. Super easy check-in and out process. The location is perfect! You’re in town and within minutes of food, shopping and local entertainment. We will definitely stay again soon. "
United States
Tracey N.
The price is ￥14,796
￥27,437 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Cozy Home in Heart of Prestonsburg
Fridge, microwave, coffee/tea maker, toaster
Tiny Home on Wheels: Your Modern Escape Awaits"

Apartment in Pikeville

Tiny Home on Wheels: Your Modern Escape Awaits"
2.0 star property
10.0 out of 10, Exceptional, (7)
"Had a great time at this little mountain getaway, would absolutely come back!"
United States
Dakota C.
The price is ￥11,273
￥20,389 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Tiny Home on Wheels: Your Modern Escape Awaits"
Microwave, oven, stovetop, dishwasher
Appalachian Hideaways Cabin #2

Cabin in Williamson

Appalachian Hideaways Cabin #2
9.6 out of 10, Exceptional, (12)
"Nice little spot to stay after a day riding the trails."
United States
Curtis J.
The price is ￥16,910
￥31,524 total
includes taxes & fees
Dec 30 - Dec 31
Appalachian Hideaways Cabin #2
Exterior
Rustic Retreat at Backwoods Bungalow – Secluded Cabin with Modern Comforts

Cabin in Pikeville

Rustic Retreat at Backwoods Bungalow – Secluded Cabin with Modern Comforts
2.0 star property
9.8 out of 10, Exceptional, (10)
"I stayed here with my mom while visiting town, and we absolutely loved it! It was clean, cozy, and had plenty of space for the two of us. The location was quiet but still convenient to everything we needed. Would definitely stay here again! "
United States
Arielle D.
The price is ￥11,978
￥22,047 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Rustic Retreat at Backwoods Bungalow – Secluded Cabin with Modern Comforts
Smart TV
Cozy Creekside Tiny Home w/ Full Kitchen - New Paint & Flooring

Cottage in Forest Hills

Cozy Creekside Tiny Home w/ Full Kitchen - New Paint & Flooring
10.0 out of 10, Exceptional, (2)
"Great spot cabin had everything we needed and was a short drive from the buffalo mountain trail head. Would gladly stay there again. Host was very nice and is local to the cabin. "
United States
Carson G.
The price is ￥15,500
￥25,093 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Cozy Creekside Tiny Home w/ Full Kitchen - New Paint & Flooring
Fridge, microwave, oven, stovetop
Cozy studio on US 23 between Pikeville and Prestonsburg

Apartment in Harold

Cozy studio on US 23 between Pikeville and Prestonsburg
2.0 star property
9.0 out of 10, Wonderful, (2)
"I have no complaints. The property was nice and comfortable. It was clean. The property manager was very easy to get ahold of and extremely. Would stay her again. "
United States
Zach S.
The price is ￥10,568
￥23,734 total
includes taxes & fees
Dec 30 - Dec 31
Cozy studio on US 23 between Pikeville and Prestonsburg
Fridge, microwave, oven, stovetop
The Nook in Downtown Pikeville

Apartment in Pikeville

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. "
United States
Dyana F.
The price is ￥13,935
￥28,501 total
includes taxes & fees
Dec 30 - Dec 31
The Nook in Downtown Pikeville
Property grounds
The Boons Camp Cabin

Cabin in Boons Camp

The Boons Camp Cabin
The price is ￥13,152
￥54,638 total
includes taxes & fees
Dec 30 - Dec 31
The Boons Camp Cabin
Fridge, microwave, stovetop, coffee/tea maker
Inspiration Station: Your Peaceful Getaway to Recharge and Refocus in Nature

Cabin in Pikeville

Inspiration Station: Your Peaceful Getaway to Recharge and Refocus in Nature
2.0 star property
8.8 out of 10, Excellent, (6)
"Great place to stay, nice new buildings. Owner is super easy to communicate with. Highly recommended!!!!👍"
United States
Lyle G.
The price is ￥15,500
￥26,836 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Inspiration Station: Your Peaceful Getaway to Recharge and Refocus in Nature
Property grounds
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access

Vacation Home in Chattaroy

Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access
9.8 out of 10, Exceptional, (9)
"Great spot, really enjoyed our stay."
United States
Seth W.
The price is ￥23,486
￥43,558 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access
Fridge, microwave, stovetop, coffee/tea maker
Ryder's Retreat overlooking the city of Williamson!

Vacation Home in Williamson

Ryder's Retreat overlooking the city of Williamson!
8.8 out of 10, Excellent, (5)
"One end of the neighborhood is sketch, other end is nice. People were nice to us in both ends."
United States
Michael K.
The price is ￥28,183
￥50,194 total
includes taxes & fees
Dec 30 - Dec 31
Ryder's Retreat overlooking the city of Williamson!
Exterior
Charming 2-bedroom cabin + loft in fabulous Salyersville with AC and WiFi

Cabin in Salyersville

Charming 2-bedroom cabin + loft in fabulous Salyersville with AC and WiFi
10.0 out of 10, Exceptional, (2)
"Secluded and peaceful. Well maintained with trails and pond to fish. Owners are extremely friendly "
United States
randy l.
The price is ￥19,571
￥46,767 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Charming 2-bedroom cabin + loft in fabulous Salyersville with AC and WiFi
8 bedrooms, WiFi, bed sheets
South Williamson Suites 8br 6 bath

Condo in South Williamson

South Williamson Suites 8br 6 bath
The price is ￥82,199
￥142,896 total
includes taxes & fees
Dec 31 - Jan 1, 2026
South Williamson Suites 8br 6 bath
Interior
Escape to Tranquility at Wanderer's Oasis – Your Boho-Inspired Cabin Retreat

Apartment in Pikeville

Escape to Tranquility at Wanderer's Oasis – Your Boho-Inspired Cabin Retreat
2.0 star property
The price is ￥10,568
￥19,607 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Escape to Tranquility at Wanderer's Oasis – Your Boho-Inspired Cabin Retreat
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

Hampton Inn Pikeville

Hampton Inn Pikeville

10/10 Excellent
"Very nice place. I have stayed here many times. "
Cynthia 1-night trip
Posted 7 days ago
Hampton Inn Pikeville

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 & Varia 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 & Varia Planetarium, whereas Archer Park and Middle Creek National Battlefield are a couple of picturesque spots to enjoy the outdoors. StoneCrest Golf Course and Jenny Wiley State Resort Park 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.