Prestonsburg Holiday Rentals

Start date: Check-in selected.
End date: Check-out
    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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Prestonsburg

Our top choices for Prestonsburg holiday rentals

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 NZ$307
includes taxes & fees
12 Sept - 13 Sept
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

3.0 star property
Near Scenic Parks: Convenient Home in Prestonsburg

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

9.8 out of 10, Exceptional, (11)
"Excellent service, very friendly"
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace

Eccentric Privy-Sleeps6. 2nd floor & outdoor deck

9.2 out of 10, Wonderful, (5)
"Walkable to downtown"
Eccentric Privy-Sleeps6. 2nd floor & outdoor deck

Appalachian Hideaways

9.0 out of 10, Wonderful, (6)
"Great place "
Appalachian Hideaways

Country Charm

10.0 out of 10, Exceptional, (37)
"Second time staying at the cabin. We had a blast! Awesome place to stay. "
Country Charm

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 NZ$688
includes taxes & fees
6 Oct - 7 Oct
Ryder's Retreat overlooking the city of Williamson!

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

Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access

9.8 out of 10, Exceptional, (6)
"Loved the house had a great experience would definitely stay again"
The price is NZ$492
includes taxes & fees
8 Sept - 9 Sept
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access

Turkey Creek Retreats

10.0 out of 10, Exceptional, (26)
"Would definitely recommend for everyone"
Turkey Creek Retreats

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!

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!

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

Appalachian Hideaways Cabin #2

9.4 out of 10, Exceptional, (10)
"Nice little spot to stay after a day riding the trails."
The price is NZ$339
includes taxes & fees
6 Sept - 7 Sept
Appalachian Hideaways Cabin #2

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!

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

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

10.0 out of 10, Exceptional, (31)
"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

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

2.0 star property
8.4 out of 10, Very good, (5)
"Great place to stay, nice new buildings. Owner is super easy to communicate with. Highly recommended!!!!👍"
The price is NZ$293
includes taxes & fees
14 Sept - 15 Sept
Inspiration Station: Your Peaceful Getaway to Recharge and Refocus in Nature
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

Top Prestonsburg Hotel Reviews

Find out more about Prestonsburg

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 favorite 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 depends 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 NZ$293 per night. Entering your travel dates in the search wizard you might find 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 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. 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 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.