Prestonsburg Holiday Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Prestonsburg

Luxury Estate nestled atop stunning mountaintop golf course!

2.0 star property
10.0 out of 10, Exceptional, (3)
"Everything was perfect from the booking to checkout. My husband and I live out of state but wanted to host our family and friends. This property exceeded expectations! The home was spacious and decorated beautifully for Christmas. It was both clean and well stocked with supplies. There is also plenty of parking. I highly recommend!"
Luxury Estate nestled atop stunning mountaintop golf course!

Cozy Home in Heart of Prestonsburg

10.0 out of 10, Exceptional, (6)
"Stopped in the area to visit family that has passed on and to find our family cemetery. Was unable to find the cemetery but still enjoyed my trip. We also visted Loretta Lynns place."
The price is AU$313
includes taxes & fees
4 Feb - 5 Feb
Cozy Home in Heart of Prestonsburg

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

Near Scenic Parks: Convenient Home in Prestonsburg

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

Williamson Cottage ~ 2 Mi to Town + Trails!

2.0 star property
7.0 out of 10, Good, (2)
"My husband, my mom, and I stayed at this cozy little cottage, and we just loved it! It was very clean, smelled amazing (like autumn), and it was just so fun! I highly recommend!"
Williamson Cottage ~ 2 Mi to Town + Trails!

Kentucky's Majestic Mountaintop Estate: The Bluegrass Palace

10.0 out of 10, Exceptional, (3)
"This was our second time staying at Bluegrass Palace. This was for our annual staff retreat for Bolts & Quarters Quilt Shop in Parkersburg, West Virginia."
Kentucky's Majestic Mountaintop Estate: The Bluegrass Palace

11 bed 7 bath large home and able to ride right from the home to the HMT trails

2.0 star property
11 bed 7 bath large home and able to ride right from the home to the HMT trails

Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails

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 with pool, Ride to trails

💙The Mountain Mama💛 Trail Riders “Home Away From Home”

10.0 out of 10, Exceptional, (25)
"Beautiful home. Tons of room. Beds everywhere. Didnt see in the add that it had a pool table in the basement! "
💙The Mountain Mama💛 Trail Riders “Home Away From Home”

Newly est. cabin close to trails, gas and great food!

10.0 out of 10, Exceptional, (31)
"The place was great and the location was perfect for us."
Newly est. cabin close to trails, gas and great food!

Rustic Retreat at Backwoods Bungalow – Secluded Cabin with Modern Comforts

2.0 star property
10.0 out of 10, Exceptional, (1)
"I had a wonderful stay at this beautiful, well-maintained, and quiet property, conveniently located near my workplace. I found it while searching for accommodations during some inclement weather. The hosts were incredibly gracious, providing thoughtful touches like farm-fresh eggs and real-time road condition updates. There's a lovely outdoor area I plan to enjoy when the weather improves. This has been, by far, the most accommodating rental I've ever experienced. I intend to stay here...
The price is AU$218
includes taxes & fees
4 Feb - 5 Feb
Rustic Retreat at Backwoods Bungalow – Secluded Cabin with Modern Comforts

NEW Entire Build 4 Studio Units by Outlaw Trails! Sleeps 15!

10.0 out of 10, Exceptional, (2)
"Great place this is second time staying at this location and would definitely book again"
NEW Entire Build 4 Studio Units by Outlaw Trails! Sleeps 15!

Country Charm

10.0 out of 10, Exceptional, (30)
"The cabin was very impressive! It was clea"
Country Charm

NEW Clean Build 2 Bed Studio Unit by Outlaw Trails! Unit 1

10.0 out of 10, Exceptional, (3)
"Very clean and easy check-in. Our 4th stay "
NEW Clean Build 2 Bed Studio Unit by Outlaw Trails! Unit 1

4 Bedroom home less than a mile to Hatfield/McCoy trails

10.0 out of 10, Exceptional, (27)
"This was a great place for me & friends to stay while in the area to ride SXS trails. Great access to Buffalo Mountain Trail and 12 miles to Devil Anse Trail. We did not receive access code & could not get into the home. We were very lucky the basement door was not locked:) "
4 Bedroom home less than a mile to Hatfield/McCoy trails

4 bedroom Trail House in Williamson, WV

9.8 out of 10, Exceptional, (37)
"We highly recommend (group of 8) We stayed right after Hurricane Helene had passed through the area. Our home owner made sure we had everything we needed to make due while the communtity dealt with a few power and water issues. She went above and beyond to make sure we weeetaken carw of. "
4 bedroom Trail House in Williamson, WV

Appalachian Hideaways

9.0 out of 10, Wonderful, (4)
"If you are there for trail riding, this location is perfect! It is also very close to gas stations, fast food places and stores. Cabin was very clean and it was so nice to have two bathrooms. We used the grill and gas fire pit which was a great addition to the cabin. Plenty of parking. Communication with the owner was great! I would definitely stay here again! "
Appalachian Hideaways

Turkey Creek Retreats

10.0 out of 10, Exceptional, (24)
"The location of this home was so conveniently located for us. It was spacious and just what we needed!"
Turkey Creek Retreats

Cozy Tiny Home Quiet 1/1 Close to Riding Trails

10.0 out of 10, Exceptional, (2)
"My husband and I stayed here for a week visiting our daughter. The property was clean and cozy. It had all the amenities we needed for the two of us. We worked remotely for a week and had very few problems. We did lose power once but we just went to a coffee shop (Lizzie B’s) which was a nice change of scenery. We did have some trouble finding it once we made the turn on the road (second house on the right) as it was dark and we didn’t have cell service. Cindy and her husband were so friendly...
The price is AU$260
includes taxes & fees
4 Feb - 5 Feb
Cozy Tiny Home Quiet 1/1 Close to Riding 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.
Don't see what you're looking for?
See all available properties in Prestonsburg
Save an average of 15% on thousands of hotels when you're signed in

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, (591)
"e"
The price is AU$184
includes taxes & fees
11 Feb - 12 Feb
Comfort Suites Prestonsburg West

Quality Inn & Suites Prestonsburg next to Mountain Arts Center

2.5 star property
8.0 out of 10, Very good, (259)
"Wonderful visit, great comfort, clean and friendly! Great breakfast "
The price is AU$191
includes taxes & fees
4 Feb - 5 Feb
Quality Inn & Suites Prestonsburg next to Mountain Arts Center

Super 8 by Wyndham Prestonsburg

2.0 star property
6.6 out of 10, (465)
"Great place "
The price is AU$104
includes taxes & fees
17 Feb - 18 Feb
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.

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?

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. Some other top choices in Prestonsburg are Cozy Home in Heart of Prestonsburg and Near Scenic Parks: Convenient Home 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 and Planetarium, whereas Archer Park and Middle Creek National Battlefield are a couple of picturesque spots to enjoy the outdoors. StoneCrest Golf Course and Jenny Wiley State Resort Park 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.