Holiday Rentals in Prestonsburg

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Holiday Rentals in Prestonsburg

The Red Dog Cottage In The Woods w/ Hot Tub
10.0 out of 10, Exceptional, (26)
"My wife and I stayed at the Red Dog Cottage for our wedding anniversary trip. The cottage and surrounding property were beautiful and meticulously cleaned and groomed. My wife and I enjoy riding ATVs and this location was perfect for that, being only .5 mile from the Hatfield McCoy trail entrance. The property owners are wonderful people and the love they have poured into this property is immediately evident the minute you set foot on it."
The Red Dog Cottage In The Woods w/ Hot Tub
'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!
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
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Jmeez cabin rentals
10.0 out of 10, Exceptional, (3)
"I really enjoyed the simple beauty of the place and the location. It was a great place to get away and relax even though it wasn't far from town."
The price is €181
includes taxes & fees
5 May - 6 May
Jmeez cabin rentals
Newly est. cabin close to trails, gas and great food!
10.0 out of 10, Exceptional, (20)
"Great place to stay, property owner was great to deal with, check-in and check-out was super easy and simple. Plenty of space to park multiple trucks and trailers. Would definitely stay here again!"
Newly est. cabin close to trails, gas and great food!
Turkey Creek Retreats
10.0 out of 10, Exceptional, (19)
"Very accommodating. Great location to ride the HM trail system."
Turkey Creek Retreats
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
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
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
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
Country Charm
10.0 out of 10, Exceptional, (25)
"We had such a great time riding and we loved going to a spot that had some privacy for us to unwind at the end of the night. We had plenty of room for our larger trailer which was a relief. Kristy and Justin were amazing host and did a great job at making you feel as if this was your home away from home. Thank you times a million."
Country Charm
Eccentric Privy-Sleeps6. 2nd floor & outdoor deck
10.0 out of 10, Exceptional, (1)
"Loved the apartment! Very clean, spacious and well decorated! Only improvement could be a wider staircase, as it’s a little difficult to get suitcases up. Overall very nice"
Eccentric Privy-Sleeps6. 2nd floor & outdoor deck
Rocky Top-luxury log Cabin next to Buffalo Mtn. Trailhead
10.0 out of 10, Exceptional, (1)
"Our host made certain we had everything we needed and graciously offered lots of local knowledge on restaurants, trails, etc. Location is so key and you have immediate access to trails and multiple towns which make for lots of exploring and new things to see. The cabin is well equipped with very comfortable beds that had all resting better than we do at home. We will definitely come stay agajn!"
Rocky Top-luxury log Cabin next to Buffalo Mtn. Trailhead
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
New 3 Bdrm unit w/ great location & ex. amenities
9.8 out of 10, Exceptional, (7)
"Another great stay! The apartment was perfect for a family visit to see our daughter at UPike! Thanks for accommodating our need to be in early."
The price is €238
includes taxes & fees
2 Jun - 3 Jun
New 3 Bdrm unit w/ great location & ex. amenities
Large 4BR Buffalo Mountain Retreat in Williamson
9.6 out of 10, Exceptional, (17)
"We had an amazing weekend full of adventures! The kids loved the game room and pool. The home owners were super and very responsive. We had a slight issue with the upstairs air conditioner and they went above and beyond to get it fixed quickly!!"
Large 4BR Buffalo Mountain Retreat in Williamson
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
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 €212
includes taxes & fees
4 May - 5 May
Jmeez cabin rentals
'homeplace' w/ Yard - 10 Mi to Jenny Wiley!
3.0 star property
8.0 out of 10, Very good, (1)
"Really liked the old house feel but very noisy by road"
'homeplace' w/ Yard - 10 Mi to Jenny Wiley!
Downtown Paintsville Vacation Rental!
8.0 out of 10, Very good, (2)
"The home and linens were clean, plenty of living space. The house is like walking into a time capsule of your grandmothers home. Very small bathrooms, drafty window AC units still installed in late November, old TVs. No grill outside was disappointing. Tight single stacked parking. There is another small house on the same lot with multiple vehicles coming and going, combined with the close neighbors and there is limited privacy and no outdoor space."
Downtown Paintsville Vacation Rental!
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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

Comfort Suites Prestonsburg West
2.5 star property
8.6 out of 10, Excellent, (533)
"The interiors are very new, which was a nice amenity. The pool area was clean and it was nice to sit by the pool and relax a little bit. The room was clean and the sofabed was helpful and a nice additional space to gather then sleep on. We could hear the neighbor in the shared room a little bit but that's usually standard for these hotels."
The price is €112
includes taxes & fees
2 Jun - 3 Jun
Comfort Suites Prestonsburg West
Jenny Wiley State Resort Park
3.0 star property
8.6 out of 10, Excellent, (361)
"It was a nice area and getaway"
The price is €115
includes taxes & fees
6 May - 7 May
Jenny Wiley State Resort Park
Quality Inn & Suites
2.5 star property
7.8 out of 10, Good, (223)
"Clean and quiet"
The price is €94
includes taxes & fees
2 Jun - 3 Jun
Quality Inn & Suites
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Prestonsburg holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Prestonsburg holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Prestonsburg holiday rentals we have selected for you start as low as €181 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 holiday 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 holiday.

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 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.

What are some of the best holiday rentals that Prestonsburg has to offer?

Turkey Creek Retreats : This holiday home rental outside of Prestonsburg is located on a river, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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.

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