Prestonsburg Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Holiday Rentals in Prestonsburg

Our top choices for Prestonsburg holiday rentals

Luxury Estate nestled atop stunning mountaintop golf course!
Interior

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
Interior

Cozy Home in Heart of Prestonsburg

10.0 out of 10, Exceptional, (8)
"Great location, quite, adequate"
The price is HK$739
HK$1,370 total
includes taxes & fees
25 Aug - 26 Aug
Cozy Home in Heart of Prestonsburg
Near Scenic Parks: Convenient Home in Prestonsburg
Interior

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
Private kitchen

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
Interior

Near Scenic Parks: Convenient Home in Prestonsburg

3.0 star property
Near Scenic Parks: Convenient Home in Prestonsburg
Trail Riders Retreat! Hatfield McCoy Trails. Private Pool. Loads of Parking!
Property grounds

Trail Riders Retreat! Hatfield McCoy Trails. Private Pool. Loads of Parking!

10.0 out of 10, Exceptional, (24)
"Great place to stay very easy trail access don’t even have to go on a main road. Very clean and a quiet place to stay. Would recommend to anyone! "
Trail Riders Retreat! Hatfield McCoy Trails. Private Pool. Loads of Parking!
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace
Interior

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

9.6 out of 10, Exceptional, (10)
"Excellent service, very friendly"
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace
'Homeplace' w/ Yard - 10 Mi to Jenny Wiley!
Exterior detail

'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!
Eccentric Privy-Sleeps6. 2nd floor & outdoor deck
Property grounds

Eccentric Privy-Sleeps6. 2nd floor & outdoor deck

9.0 out of 10, Wonderful, (4)
"Walkable to downtown"
Eccentric Privy-Sleeps6. 2nd floor & outdoor deck
Country Charm
Fridge, microwave, oven, stovetop

Country Charm

10.0 out of 10, Exceptional, (35)
"Second time staying at the cabin. We had a blast! Awesome place to stay. "
Country Charm
4 Bedroom home less than a mile to Hatfield/McCoy trails
Interior

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

10.0 out of 10, Exceptional, (30)
"Cute little house! Drive way was steep with truck and trailer but overall no complaints!"
4 Bedroom home less than a mile to Hatfield/McCoy trails
The Red Dog Chalet Couples Retreat w/ Hot Tub
Interior

The Red Dog Chalet Couples Retreat w/ Hot Tub

9.4 out of 10, Exceptional, (9)
"I stayed here for a couple days getaway and to see a concert. The owners were very kind, and informative. The place itself could honestly fall into the luxury getaway homes. Stunning landscaping and every detail of the home inside and out was simply above and beyond my expectations. "
The Red Dog Chalet Couples Retreat w/ Hot Tub
Cozy Tiny Home Quiet 1/1 Close to Riding Trails
Interior

Cozy Tiny Home Quiet 1/1 Close to Riding Trails

10.0 out of 10, Exceptional, (4)
"Very nice places. Clean and cute. Love the surrounding Mountain View’s. Definitely on my list to stay again."
Cozy Tiny Home Quiet 1/1 Close to Riding Trails
New 3 Bdrm unit w/ great location & ex. amenities
3 bedrooms, desk, iron/ironing board, travel cot

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

9.6 out of 10, Exceptional, (16)
"This place is exactly as advertised and quieter than expected. Hostess thought of everything. Lovely place for my family of 5. "
New 3 Bdrm unit w/ great location & ex. amenities
Private Cottage Near The Lake with 3 bedrooms, 2 baths, and a gameroom!
Fridge, microwave, oven, stovetop

Private Cottage Near The Lake with 3 bedrooms, 2 baths, and a gameroom!

9.4 out of 10, Exceptional, (3)
"Fully furnished pit stop for your mountain activities....People are very nice...thanks Curtis :-)"
Private Cottage Near The Lake with 3 bedrooms, 2 baths, and a gameroom!
Appalachian Hideaways Cabin #2
Microwave, oven, stovetop, dishwasher

Appalachian Hideaways Cabin #2

9.4 out of 10, Exceptional, (10)
"Very nice place would stay again "
The price is HK$844
HK$1,574 total
includes taxes & fees
26 Aug - 27 Aug
Appalachian Hideaways Cabin #2
The Nook in Downtown Pikeville
Fridge, microwave, oven, stovetop

The Nook in Downtown 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. "
The Nook in Downtown Pikeville
11 bed 7 bath large home and able to ride right from the home to the HMT trails
Exterior

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
Appalachian Hideaways
Living area

Appalachian Hideaways

9.0 out of 10, Wonderful, (6)
"Great place "
Appalachian Hideaways
Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to trails
Outdoor pool

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

9.6 out of 10, Exceptional, (21)
"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. "
Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to 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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Prestonsburg Hotel Reviews

Comfort Suites Prestonsburg West

Comfort Suites Prestonsburg West

10/10 Excellent
"The staff was great. Both times I’ve stayed here though I’ve noticed the doors are very difficult to close. My door this time could be open without even using the room key when I first checked in. You have to use some muscle to get it to latch. "
Ryan 1-night trip
Posted 1 day ago
Comfort Suites Prestonsburg West

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 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.