Prestonsburg Vacation Rentals

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Oct 31 - Nov 2
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Nov 14 - Nov 16
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Dec 12 - Dec 14
In three months
Jan 9 - Jan 11

Vacation Rentals in Prestonsburg

Interior
Luxury Estate nestled atop stunning mountaintop golf course!
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!
Interior
Cozy Home in Heart of Prestonsburg
Cozy Home in Heart of Prestonsburg
10.0 out of 10, Exceptional, (8)
"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. "
$155 nightly
The price is $175
Oct 20 - Oct 21
Total with taxes and fees
Cozy Home in Heart of Prestonsburg
Private kitchen
New to the area? Stop by and see the most recent bachelor pad on the scene
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
House (1 Bedroom) | Interior
Near Scenic Parks: Convenient Home in Prestonsburg
Near Scenic Parks: Convenient Home in Prestonsburg
3.0 star property
Near Scenic Parks: Convenient Home in Prestonsburg
Interior
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace
9.8 out of 10, Exceptional, (11)
"Great place to stay for our family. Loved everything about the location, house, pool, and overall value."
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace
Exterior
Turkey Creek Retreats
Turkey Creek Retreats
10.0 out of 10, Exceptional, (28)
"Would stay there again."
Turkey Creek Retreats
Exterior
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
2.0 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
Outdoor pool
Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails
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
Fridge, microwave, coffee/tea maker, toaster
Tiny Home on Wheels: Your Modern Escape Awaits"
Tiny Home on Wheels: Your Modern Escape Awaits"
2.0 star property
10.0 out of 10, Exceptional, (5)
"Had a great time at this little mountain getaway, would absolutely come back!"
$113 nightly
The price is $125
Oct 28 - Oct 29
Total with taxes and fees
Tiny Home on Wheels: Your Modern Escape Awaits"
Property grounds
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access
9.8 out of 10, Exceptional, (7)
"Loved the house had a great experience would definitely stay again"
$276 nightly
The price is $299
Nov 12 - Nov 13
Total with taxes and fees
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access
3 bedrooms, desk, iron/ironing board, travel crib
New 3 Bdrm unit w/ great location & ex. amenities
New 3 Bdrm unit w/ great location & ex. amenities
9.6 out of 10, Exceptional, (19)
"The property is in a great location in Pikeville. You can walk to several restaurants and the venue where we seen the Red Clay Strays! It was clean and spacious and just a fantastic place to stay in Pikeville, KY."
New 3 Bdrm unit w/ great location & ex. amenities
Fridge, microwave, oven, stovetop
The Nook in Downtown 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. "
The Nook in Downtown Pikeville
Fridge, microwave, oven, stovetop
Private Cottage Near The Lake with 3 bedrooms, 2 baths, and a gameroom!
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!
Living area
Appalachian Hideaways
Appalachian Hideaways
9.2 out of 10, Wonderful, (7)
"Great place "
Appalachian Hideaways
Property grounds
Trail Riders Retreat! Hatfield McCoy Trails. Private Pool. Loads of Parking!
Trail Riders Retreat! Hatfield McCoy Trails. Private Pool. Loads of Parking!
10.0 out of 10, Exceptional, (26)
"We had a excellent time very close to trails pool is very nice house was very clean host are super nice "
Trail Riders Retreat! Hatfield McCoy Trails. Private Pool. Loads of Parking!
Fridge, microwave, oven, stovetop
Country Charm
Country Charm
10.0 out of 10, Exceptional, (38)
"Second time staying at the cabin. We had a blast! Awesome place to stay. "
Country Charm
Fridge, microwave, stovetop, coffee/tea maker
Inspiration Station: Your Peaceful Getaway to Recharge and Refocus in Nature
Inspiration Station: Your Peaceful Getaway to Recharge and Refocus in Nature
2.0 star property
8.4 out of 10, Very Good, (5)
"Great place to stay, nice new buildings. Owner is super easy to communicate with. Highly recommended!!!!👍"
$136 nightly
The price is $151
Oct 28 - Oct 29
Total with taxes and fees
Inspiration Station: Your Peaceful Getaway to Recharge and Refocus in Nature
2 bedrooms, free WiFi, bed sheets
The Red Dog Cottage In The Woods w/ Hot Tub
The Red Dog Cottage In The Woods w/ Hot Tub
10.0 out of 10, Exceptional, (39)
"The nicest place iv stayed so far. Beautiful house. The hosts are very nice people. My next teip will definitely stay again."
The Red Dog Cottage In The Woods w/ Hot Tub
Fridge, microwave, stovetop, coffee/tea maker
Ryder's Retreat overlooking the city of 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."
$310 nightly
The price is $345
Nov 6 - Nov 7
Total with taxes and fees
Ryder's Retreat overlooking the city of Williamson!
Interior
4 Bedroom home less than a mile to Hatfield/McCoy trails
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
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

Quality Inn & Suites Prestonsburg next to Mountain Arts Center

Quality Inn & Suites Prestonsburg next to Mountain Arts Center

10/10 Excellent
"Everything was nice. "
Deanna 1-night trip
Posted 3 days ago
Quality Inn & Suites Prestonsburg next to Mountain Arts Center

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 $125 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.