Prestonsburg Holiday Rentals

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Holiday Rentals in Prestonsburg

Holiday Home in Prestonsburg

2.0 star property
10.0 out of 10, Exceptional, (7)
"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!"
United States
Leigh W.
Luxury Estate nestled atop stunning mountaintop golf course!

Holiday 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.
The price is AU$268
includes taxes & fees
16 Dec - 17 Dec
Cozy Home in Heart of Prestonsburg

Apartment in Prestonsburg

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. "
United States
Glenda
New to the area? Stop by and see the most recent bachelor pad on the scene

Cottage in Prestonsburg

3.0 star property
Near Scenic Parks: Convenient Home in Prestonsburg

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.
The price is AU$232
includes taxes & fees
4 Jan - 5 Jan 2026
Rustic Retreat at Backwoods Bungalow – Secluded Cabin with Modern Comforts

Chalet in Williamson

9.6 out of 10, Exceptional, (12)
"Communication was great. The owner reached out the day before our arrival and provided check-in information and some suggestions for things we might want to check out in the area. The Red Dog Chalet was beautiful, cozy, and immaculately clean. We were very pleased with the whole experience. "
United States
Wiley E.
The Red Dog Chalet Couples Retreat w/ Hot Tub

Holiday Home in Langley

9.8 out of 10, Exceptional, (15)
"Great place to stay for our family. Loved everything about the location, house, pool, and overall value."
United States
Rick S.
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace

Cabin in Pikeville

2.0 star property
8.8 out of 10, Excellent, (6)
"Great place to stay, nice new buildings. Owner is super easy to communicate with. Highly recommended!!!!👍"
United States
Lyle G.
The price is AU$255
includes taxes & fees
14 Dec - 15 Dec
Inspiration Station: Your Peaceful Getaway to Recharge and Refocus in Nature

Apartment in Pikeville

9.6 out of 10, Exceptional, (8)
"Walkable to downtown"
United States
Brian G.
Eccentric Privy-Sleeps6. 2nd floor & outdoor deck

Cabin in Williamson

9.2 out of 10, Wonderful, (9)
"Great place "
United States
Bruce
Appalachian Hideaways

Holiday Home in Williamson

10.0 out of 10, Exceptional, (28)
"We had a excellent time very close to trails pool is very nice house was very clean host are super nice "
United States
Seth L.
Trail Riders Retreat! Hatfield McCoy Trails. Private Pool. Loads of Parking!

Holiday Home in Williamson

2.0 star property
9.4 out of 10, Exceptional, (3)
"This was a very big house the slept 16 adults comfortably with rooms to spare. We had a wonderful time. We came to ride sxs in the trails. Very close to trails, gas and restaurants."
United States
Brandi F.
11 bed 7 bath large home and able to ride right from the home to the HMT trails

Cottage in Williamson

10.0 out of 10, Exceptional, (40)
"The nicest place iv stayed so far. Beautiful house. The hosts are very nice people. My next teip will definitely stay again."
United States
Gregory S.
The Red Dog Cottage In The Woods w/ Hot Tub

Holiday Home in Williamson

9.8 out of 10, Exceptional, (17)
"This was a fantastic place to stay! Clean,quiet with tons of room for family fun"
United States
deb r.
Creek View Retreat 3 Bedroom- 2 Full Bathroom. Cozy home

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.
The price is AU$279
includes taxes & fees
20 Dec - 21 Dec
The Nook in Downtown Pikeville

Holiday Home in Williamson

9.4 out of 10, Exceptional, (24)
"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. "
United States
eddie h.
Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails

Cabin in Williamson

10.0 out of 10, Exceptional, (41)
"Second time staying at the cabin. We had a blast! Awesome place to stay. "
United States
Raymond P.
Country Charm

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.
The price is AU$307
includes taxes & fees
10 Dec - 11 Dec
Appalachian Hideaways Cabin #2

Holiday Home in Williamson

10.0 out of 10, Exceptional, (33)
"Such a peaceful spot high up on the hill! "
United States
Margaret P.
4 Bedroom home less than a mile to Hatfield/McCoy trails

Holiday Home in 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."
United States
Michael K.
The price is AU$490
includes taxes & fees
5 Dec - 6 Dec
Ryder's Retreat overlooking the city of Williamson!
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

Find out more about Prestonsburg

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, 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 favourite 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 depend 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 AU$232 per night. Entering your travel dates in the search wizard might find you 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 & Varia 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?

Luxury Estate nestled atop stunning mountaintop golf course!: This highly rated holiday home rental in Prestonsburg offers a patio, a garden and a BBQ 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 that you can cook with friends or family. Make the most of games in this rental home to help you unwind. Our travellers also rate Cozy Home in Heart of Prestonsburg as a favourite home for rent in Prestonsburg.

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 & 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 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.