Prestonsburg Holiday Rentals

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Holiday Rentals in Prestonsburg

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 HK$1,121
HK$1,869 total
includes taxes & fees
26 Nov - 27 Nov
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

Luxury Estate nestled atop stunning mountaintop golf course!

2.0 star property
10.0 out of 10, Exceptional, (1)
"We were coming to town to celebrate my son's wedding and we needed a big house. Not easy to find in this area. This house fit the bill and was simply AMAZING! The house is easily the best house that we have ever stayed at...hands down! Plenty of rooms and everything you could ever need to play, cook, and relax with family and friends. I could not more highly recommend this house. We LOVED it!!! John"
Luxury Estate nestled atop stunning mountaintop golf course!

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

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!

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

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!

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

10.0 out of 10, Exceptional, (24)
"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”

The Red Dog Chalet Couples Retreat w/ Hot Tub

9.2 out of 10, Wonderful, (5)
"Location and the red dog chalet is beautiful! Chalet is clean and cozy! Close to trails for riding. Host is very personable, wonderful and kind. We would love to come back one day! Highly recommend!"
The Red Dog Chalet Couples Retreat w/ Hot Tub

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

New 3 Bdrm unit w/ great location & ex. amenities

9.6 out of 10, Exceptional, (12)
"We came to Pikeville for our wedding shower and had such an amazing time at this property! It was very clean and had everything we needed. Would definitely recommend! "
The price is HK$1,627
HK$2,102 total
includes taxes & fees
27 Nov - 28 Nov
New 3 Bdrm unit w/ great location & ex. amenities

'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!

10.0 out of 10, Exceptional, (16)
"Lovely home that easily accommodated our little family gathering. Perfect place for us to be together after 6 long years!"
'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!

Ryder's Retreat overlooking the city of Williamson!

8.8 out of 10, Excellent, (5)
"The owner was very quick at responding, and willing to alleviate any concerns immediately. The property was very clean and well taken care of. The inside had many cosmetic upgrades. There were a few minor broken things (toilet paper holder broketoilet lidtttoilet lid"
The price is HK$1,557
HK$2,686 total
includes taxes & fees
24 Nov - 25 Nov
Ryder's Retreat overlooking the city of Williamson!

Appalachian Hideaways

8.8 out of 10, Excellent, (3)
"I reserved this place for employees we had working in the area. This place was perfect for their needs. They each had their own bedroom and bathroom, add in the comforts of home and it was the perfect place for them to relax after a long days work. Everything was clean, check in was easy, wifi worked great. The host is excellent! We communicated back and forth several times. She is exceptionally responsive and informative."
Appalachian Hideaways

Jmeez cabin rentals

8.4 out of 10, Very good, (7)
"Great place for a couple of people who want to ride Hatfield and McCoy trails!"
The price is HK$973
HK$1,489 total
includes taxes & fees
24 Nov - 25 Nov
Jmeez cabin rentals

The Red Dog Cottage In The Woods w/ Hot Tub

10.0 out of 10, Exceptional, (33)
"The Red Dog Cottage is second to none! It is more beautiful than the pics show! The owners are wonderful and provide the best hospitality. We had such a fun time riding trails and coming back to the cottage to relax and unwind! Highly recommend staying at the Red Dog Cottage!"
The Red Dog Cottage In The Woods w/ Hot Tub

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 Cabin #2

10.0 out of 10, Exceptional, (4)
"Enjoyed staying in cabin. Very roomy compared to pics in ad. Definitely would stay here again."
The price is HK$934
HK$1,680 total
includes taxes & fees
25 Nov - 26 Nov
Appalachian Hideaways Cabin #2

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
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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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, (581)
"I stayed here for a mountain bike race at Sugarcamp Mountain. I enjoyed my stay here. Parking was great, everything was clean, the staff were kind, etc. I'd happily stay here again - and probably will for next year's race!"
The price is HK$725
HK$822 total
includes taxes & fees
22 Dec - 23 Dec
Comfort Suites Prestonsburg West

Quality Inn & Suites

2.5 star property
8.0 out of 10, Very good, (254)
"The room was nice and clean and there was an excellent breakfast. One question, I was charged on my credit card $286.36 by Expedia, but the Quality Inn gave me a receipt for $213.96. Why was there such a different in the charge?"
The price is HK$551
HK$624 total
includes taxes & fees
19 Dec - 20 Dec
Quality Inn & Suites

Jenny Wiley State Resort Park

3.0 star property
8.6 out of 10, Excellent, (393)
"The property was clean and staff friendly"
Jenny Wiley State Resort Park
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.
Beautiful view of the beach with palm trees

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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.