Prestonsburg Vacation Rentals

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Vacation Rentals in Prestonsburg

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 CA $144
CA $265 total
includes taxes & fees
Jun 10 - Jun 11
Cozy Home in Heart of Prestonsburg
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
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
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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
Ryder's Retreat overlooking the city of Williamson!
8.0 out of 10, Very good, (1)
"Parking will hold 4 trucks with trailers and this includes on street parking and the gravel parking area. We had to park a car on the trailer so we had room for the side by sides to park in the gravel area. There is no privacy other than bathrooms. The house otherwise was clean and held 10 guests. There are alot of run down or abandoned properties right around the area. There was alot of late night traffic."
Ryder's Retreat overlooking the city of Williamson!
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
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!
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
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 CA $170
CA $303 total
includes taxes & fees
Jun 7 - Jun 8
Jmeez cabin rentals
Turkey Creek Retreats
10.0 out of 10, Exceptional, (21)
"We rented this house to join friends on a sxs trip. It was a cute cozy home and great location! The owners were very nice! Thanks, Tina for allowing us to stay in your home!"
Turkey Creek Retreats
Private entire home • Pikeville • 6 min. drive from PMC
9.6 out of 10, Exceptional, (10)
"We enjoyed our stay in Pikeville. The property was perfect for us. It was very clean and the owners were really nice. Will definitely stay there again."
Private entire home • Pikeville • 6 min. drive from PMC
New 3 Bdrm unit w/ great location & ex. amenities
9.8 out of 10, Exceptional, (9)
"This was our third stay here. The property is clean, well-located and comfortable. The Host is very nice and communication is excellent."
The price is CA $271
CA $354 total
includes taxes & fees
Jun 16 - Jun 17
New 3 Bdrm unit w/ great location & ex. amenities
'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!
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 CA $170
CA $259 total
includes taxes & fees
Jun 19 - Jun 20
Jmeez cabin rentals
The Red Dog Cottage In The Woods w/ Hot Tub
10.0 out of 10, Exceptional, (29)
"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
Appalachian Hideaways Cabin #2
10.0 out of 10, Exceptional, (1)
"It was great"
The price is CA $164
CA $294 total
includes taxes & fees
Jun 6 - Jun 7
Appalachian Hideaways Cabin #2
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
Cozy Apartment embedded in Kentucky mountains. Pet friendly.
10.0 out of 10, Exceptional, (4)
"Out of the city, but close to major roads. So getting around is very convenient. My only real issue was: no ceiling fans. But the a/c works just fine in lieu. Better value and more space than local hotels."
Cozy Apartment embedded in Kentucky mountains. Pet friendly.
💙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”
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
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

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 CA $186
CA $225 total
includes taxes & fees
Jun 6 - Jun 7
Jenny Wiley State Resort Park
Comfort Suites Prestonsburg West
2.5 star property
8.6 out of 10, Excellent, (538)
"Super clean and updated! New carpeting, painting, and fixtures. Cleanliness seemed a priority. The coffee cups were individually wrapped. The breakfast was very good. Eggs, sausage, biscuits and gravy along with all the usuals. Well done and tasty! Highly recommend this hotel…."
The price is CA $142
CA $161 total
includes taxes & fees
Jun 9 - Jun 10
Comfort Suites Prestonsburg West
Super 8 by Wyndham Prestonsburg
2.0 star property
6.4 out of 10, (417)
"So basically, my thinking is that the base rating for a hotel should be a 3/5. I liked the shower pressure so that brought it up a point, and I also thought the beds were comfortable so that also brings it up another point. However, the building is like in disrepair and falling apart to the point where I have to take a point away as funny as it was. No bugs or inconveniences or anything like that, but I don’t feel like it deserves to be on the same level as like Embassy Suites and Home2. So to...
The price is CA $92
CA $101 total
includes taxes & fees
Jul 3 - Jul 4
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.

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Prestonsburg vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Prestonsburg vacation rentals we have selected for you start as low as CA $144 per night. Entering your travel dates in the search wizard 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. 

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?

Large 4BR Buffalo Mountain Retreat in Williamson: This vacation home rental outside of Prestonsburg is located in the city center and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

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 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 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.

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