Prestonsburg Holiday Rentals

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Holiday Rentals in Prestonsburg

Interior
Cozy Home in Heart of Prestonsburg
10.0 out of 10, Exceptional, (5)
"House is clean and decor is great. Location to town is easy and a walkable distance. Enjoyed Prestonsburg and surrounding areas. Property manager was very responsive. Great place!"
The price is NZ$317
per night
10 Jun - 11 Jun
Cozy Home in Heart of Prestonsburg
TV, video games
Perfect Lake Getaway!!
Perfect Lake Getaway!!
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
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Fridge, microwave, oven, stovetop
4 Bedroom home less than a mile to Hatfield/McCoy trails
10.0 out of 10, Exceptional, (23)
"Great place and hosts. Super close to what we needed. Would definitely book again in the future!"
4 Bedroom home less than a mile to Hatfield/McCoy trails
Shower, hair dryer, towels, soap
Large 4BR Buffalo Mountain Retreat in Williamson
9.6 out of 10, Exceptional, (19)
"We had a great time. The house is beautiful and very spacious. Location is perfect because it’s close to everything. Neighbors were very nice! Host was super nice and very accommodating. We will definitely come back and stay again! Dirt Days was a lot of fun for us and my nephews. The vendors were very friendly. The town has a lot of cool history."
Large 4BR Buffalo Mountain Retreat in Williamson
Exterior
Appalachian Hideaways
10.0 out of 10, Exceptional, (1)
"We had a great time. Everything was very clean and owner was very helpful anyway she needed to be. If we ever go back that way we would stay here again!!"
Appalachian Hideaways
2 bedrooms, free WiFi, bed sheets
The Red Dog Cottage In The Woods w/ Hot Tub
10.0 out of 10, Exceptional, (28)
"The Red Dog Cottage is absolutely amazing! By far the nicest and best kept VRBO that we have ever stayed at. It had everything that we needed for our riding trip and is in a great location for single track riders. The hot tub was a wonderful surprise and very relaxing after a long day of riding. The Cool's are wonderful hosts! We appreciated the pre-arrival call and all of the information they provided. Their attention to detail, design, and the work put into the property is quite impressive."
The Red Dog Cottage In The Woods w/ Hot Tub
Smart TV
Newly est. cabin close to trails, gas and great food!
10.0 out of 10, Exceptional, (22)
"It was our second time back with our whole quad squad Framily crew and even all the kids loved it. The area is just beautiful and there's plenty of yard room to do fun activities and have the small kiddos ride around. Close to trails and can ride the quad pretty much anywhere. Brandon is always amazing with replying to messages and being quick about it. They're fantastic people to rent from and we will be continuing to go back bc we love it and them so much!!"
Newly est. cabin close to trails, gas and great food!
Exterior
Turkey Creek Retreats
10.0 out of 10, Exceptional, (20)
"Spent two nights here in early May. The place was clean and comfortable and very convenient to many places of interest."
Turkey Creek Retreats
Exterior
'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!
10.0 out of 10, Exceptional, (14)
"The most clean rental I’ve ever been in. Loved the authenticity of the home."
'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!
Fridge, microwave, stovetop, coffee/tea maker
Ryder's Retreat overlooking the city of Williamson!
Ryder's Retreat overlooking the city of Williamson!
Exterior
Jmeez cabin rentals
10.0 out of 10, Exceptional, (4)
"Just what we needed for a weekend riding the trails. A place to sleep and shower."
The price is NZ$312
per night
26 May - 27 May
Jmeez cabin rentals
Private kitchen
Appalachian Hideaways Cabin #2
The price is NZ$354
per night
27 May - 28 May
Appalachian Hideaways Cabin #2
Exterior
4 bedroom Trail House in Williamson, WV
9.8 out of 10, Exceptional, (34)
"Ashley was a wonderful host. She responded to all questions promptly and had plenty of information on Hatfield McCoy trails near the house. She left a list of nearby restaurants and SXS repair shops. House is in a quiet neighborhood. We plan to stay here again."
4 bedroom Trail House in Williamson, WV
Fridge, oven, stovetop
Cozy Apartment embedded in Kentucky mountains. Pet friendly.
10.0 out of 10, Exceptional, (3)
"The owner has excellent communication. When you walk in, everything smells nice and fresh. Just a quick trip to the golf course where my daughter was playing."
The price is NZ$202
per night
27 May - 28 May
Cozy Apartment embedded in Kentucky mountains. Pet friendly.
Exterior
💙The Mountain Mama💛 Trail Riders “Home Away From Home”
10.0 out of 10, Exceptional, (21)
"Great place to stay for the trails. Host was awesome! House house was nice and clean. Short ride by bike to Buffalo Mountain. Definitely would stay here again."
💙The Mountain Mama💛 Trail Riders “Home Away From Home”
Aerial view
Cozy trail house at the Hatfield McCoy Trails
10.0 out of 10, Exceptional, (31)
"Owner was great! Location great! Trails great! House great! We all loved everything about it!"
Cozy trail house at the Hatfield McCoy Trails
Interior
The Red Dog Chalet Couples Retreat w/ Hot Tub
10.0 out of 10, Exceptional, (2)
"Beautiful place & close HMT & outlaw trails. Highly recommended"
The Red Dog Chalet Couples Retreat w/ Hot Tub
Exterior
Jmeez cabin rentals
8.6 out of 10, Excellent, (8)
"Property was clean and worked well for our needs. Only issue we had is there were no blankets for beds or sheets for pullout"
The price is NZ$363
per night
27 May - 28 May
Jmeez cabin rentals
Property grounds
Creek View Retreat 3 Bedroom- 2 Full Bathroom. Cozy home
10.0 out of 10, Exceptional, (9)
"We went riding from here for the second time and both times the riding and the house were great. There is plenty of room inside and out and the house is always very clean."
Creek View Retreat 3 Bedroom- 2 Full Bathroom. Cozy home
Don't see what you're looking for?
See all available properties in Prestonsburg
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.

Other types of properties in Prestonsburg you may be interested in

Lake
Jenny Wiley State Resort Park
3.0 star property
8.4 out of 10, Very good, (366)
"It was a nice area and getaway"
The price is NZ$269
per night
2 Jun - 3 Jun
Jenny Wiley State Resort Park
Suite, 1 King Bed with Sofa bed, Accessible, Non Smoking
Comfort Suites Prestonsburg West
2.5 star property
8.6 out of 10, Excellent, (537)
"It was great. Everyone was very friendly and helpful to use. Well stay there again."
The price is NZ$204
per night
27 May - 28 May
Comfort Suites Prestonsburg West
Exterior
Super 8 by Wyndham Prestonsburg
2.0 star property
6.4 out of 10, (406)
"The hotel is run down, needs some updating. "
The price is NZ$121
per night
1 Jun - 2 Jun
Super 8 by Wyndham Prestonsburg
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Prestonsburg holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Prestonsburg. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Prestonsburg. Seeing all the best attractions is bound to make you fall in love with Prestonsburg. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Prestonsburg short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Prestonsburg?

Yes, there are holiday rentals in Prestonsburg close to East Kentucky Science Center and Planetarium, or you can select 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 theatres during your trip.

How many holiday rentals will I find in Prestonsburg?

Expedia has 3 holiday 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 Jenny Wiley State Resort Park and Archer 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 holiday rental in Prestonsburg like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Prestonsburg. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for families.

Recent reviews of Prestonsburg properties
Expedia verified reviews