Prestonsburg Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Prestonsburg

Interior
Cozy Home in Heart of Prestonsburg

Vacation Home in 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.
$155 nightly
The price is $175
Dec 15 - Dec 16
Total with taxes and fees
Cozy Home in Heart of Prestonsburg
Microwave, oven, stovetop, dishwasher
Appalachian Hideaways Cabin #2

Cabin in Williamson

9.6 out of 10, Exceptional, (12)
"Nice little spot to stay after a day riding the trails."
United States
Curtis J.
$181 nightly
The price is $201
Dec 6 - Dec 7
Total with taxes and fees
Appalachian Hideaways Cabin #2
Fridge, microwave, coffee/tea maker, toaster
Tiny Home on Wheels: Your Modern Escape Awaits"

Apartment in Pikeville

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.
$122 nightly
The price is $135
Dec 7 - Dec 8
Total with taxes and fees
Tiny Home on Wheels: Your Modern Escape Awaits"
Exterior
Rustic Retreat at Backwoods Bungalow – Secluded Cabin with Modern Comforts

Cabin in Pikeville

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.
$135 nightly
The price is $150
Jan 4 - Jan 5, 2026
Total with taxes and fees
Rustic Retreat at Backwoods Bungalow – Secluded Cabin with Modern Comforts
Property grounds
The Boons Camp Cabin

Cabin in Boons Camp

$348 nightly
The price is $351
Dec 7 - Dec 8
Total with taxes and fees
The Boons Camp Cabin
Fridge, microwave, oven, stovetop
Cozy studio on US 23 between Pikeville and Prestonsburg

Apartment in Harold

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.
$138 nightly
The price is $152
Dec 7 - Dec 8
Total with taxes and fees
Cozy studio on US 23 between Pikeville and Prestonsburg
Smart TV
Cozy Creekside Tiny Home w/ Full Kitchen - Walk to Distillery

Cottage in Forest Hills

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.
$125 nightly
The price is $139
Dec 8 - Dec 9
Total with taxes and fees
Cozy Creekside Tiny Home w/ Full Kitchen - Walk to Distillery
Property grounds
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access

Vacation Home in Chattaroy

9.8 out of 10, Exceptional, (8)
"This location was perfect for our big group! "
United Kingdom
Dion V.
$257 nightly
The price is $278
Dec 8 - Dec 9
Total with taxes and fees
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access
Fridge, microwave, oven, stovetop
The Nook in Downtown Pikeville

Apartment in 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.
$159 nightly
The price is $182
Dec 19 - Dec 20
Total with taxes and fees
The Nook in Downtown Pikeville
Exterior
Charming 2-bedroom cabin + loft in fabulous Salyersville with AC and WiFi

Cabin in Salyersville

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.
$280 nightly
The price is $300
Dec 8 - Dec 9
Total with taxes and fees
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

$820 nightly
The price is $913
Dec 31 - Jan 1, 2026
Total with taxes and fees
South Williamson Suites 8br 6 bath
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

Ramada Hotel & Conference Center by Wyndham Paintsville

Ramada Hotel & Conference Center by Wyndham Paintsville

10/10 Excellent
"Very clean and comfortable stay. I wish they would’ve had a lounge and a restaurant that was open at night."
Joseph 2-night trip
Posted 5 days ago
Ramada Hotel & Conference Center by Wyndham Paintsville

Find out more about Prestonsburg

Everything you need to know about Prestonsburg vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Prestonsburg vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Prestonsburg vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Prestonsburg vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Prestonsburg. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Prestonsburg in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $150 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Prestonsburg rentals

At Expedia, we put the best Prestonsburg vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Prestonsburg rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Prestonsburg vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Prestonsburg. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 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.