Prestonsburg Vacation Rentals

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Vacation Rentals in Prestonsburg

Luxury Estate nestled atop stunning mountaintop golf course!

2.0 star property
10.0 out of 10, Exceptional, (6)
"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, (8)
"Great location, quite, adequate"
The price is CA $129
CA $240 total
includes taxes & fees
Jul 28 - Jul 29
Cozy Home in Heart of Prestonsburg

Near Scenic Parks: Convenient Home in Prestonsburg

10.0 out of 10, Exceptional, (2)
"The inside was decorated beautifully, Loved the garage And( even though we didnt use) washer and dryer."
Near Scenic Parks: Convenient Home in 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

3.0 star property
Near Scenic Parks: Convenient Home in Prestonsburg

Rustic Retreat at Backwoods Bungalow – Secluded Cabin with Modern Comforts

2.0 star property
10.0 out of 10, Exceptional, (6)
"I liked that the property was very secluded and quiet the owner was very cool and was easy going I also loved the cabin feel for the property I was there for a weekend and enjoyed my stay the picture doesn't do any justice the inside is bigger than it looks "
Rustic Retreat at Backwoods Bungalow – Secluded Cabin with Modern Comforts

Creek View Retreat 3 Bedroom- 2 Full Bathroom. Cozy home

9.8 out of 10, Exceptional, (15)
"Great 4 wheeling from this location and a beautiful house. "
Creek View Retreat 3 Bedroom- 2 Full Bathroom. Cozy home

Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace

10.0 out of 10, Exceptional, (7)
"Excellent service, very friendly"
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace

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

10.0 out of 10, Exceptional, (23)
"It was a great place to stay. We ride electric bikes. There were quite a few trails with easy access available. House was wonderful to stay in. Very neat and tidy."
'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!

Ryder's Retreat overlooking the city of 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."
The price is CA $308
CA $517 total
includes taxes & fees
Jul 27 - Jul 28
Ryder's Retreat overlooking the city of Williamson!

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

9.6 out of 10, Exceptional, (15)
"This place is exactly as advertised and quieter than expected. Hostess thought of everything. Lovely place for my family of 5. "
The price is CA $287
CA $371 total
includes taxes & fees
Jul 21 - Jul 22
New 3 Bdrm unit w/ great location & ex. amenities

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!

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

9.6 out of 10, Exceptional, (21)
"Beautiful house"
Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails

The Nook in Downtown Pikeville

8.8 out of 10, Excellent, (3)
"Small clean apartment like accommodations. Nicer than any hotel room I’ve stayed at in Pikeville and the price was great. "
The Nook in Downtown Pikeville

Appalachian Hideaways Cabin #2

9.8 out of 10, Exceptional, (8)
"Very nice place would stay again "
The price is CA $148
CA $276 total
includes taxes & fees
Jul 22 - Jul 23
Appalachian Hideaways Cabin #2

Cozy trail house at the Hatfield McCoy Trails

10.0 out of 10, Exceptional, (39)
"Came here for a work trip and really enjoyed the home, our crew came to work at a local project and were blessed to stay here rather than a hotel. I can speak for the rest of the crew, we would absolutely stay and vacation here."
Cozy trail house at the Hatfield McCoy Trails

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

2.0 star property
10.0 out of 10, Exceptional, (1)
11 bed 7 bath large home and able to ride right from the home to the HMT trails

Inspiration Station: Your Peaceful Getaway to Recharge and Refocus in Nature

2.0 star property
7.4 out of 10, Good, (3)
"Great place to stay, nice new buildings. Owner is super easy to communicate with. Highly recommended!!!!👍"
The price is CA $117
CA $214 total
includes taxes & fees
Aug 10 - Aug 11
Inspiration Station: Your Peaceful Getaway to Recharge and Refocus in Nature

The Red Dog Cottage In The Woods w/ Hot Tub

10.0 out of 10, Exceptional, (39)
"Place is beautiful, cozy, relaxing, and will be back in the future!"
The Red Dog Cottage In The Woods w/ Hot Tub

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

10.0 out of 10, Exceptional, (28)
"Nice place to stray close to town and close to the utv trails! Enjoyed our stay!"
💙The Mountain Mama💛 Trail Riders “Home Away From Home”
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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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?

Luxury Estate nestled atop stunning mountaintop golf course!: Visitors give good reviews to this Prestonsburg vacation home rental, which offers a patio, a garden, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection 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 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 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 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.