Prestonsburg Holiday Rentals

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Holiday Rentals in Prestonsburg

Luxury Estate nestled atop stunning mountaintop golf course!
2.0 star property
10.0 out of 10, Exceptional, (6)
"The house is beautiful, and located in the mountains overlooking breathtaking scenery. It is surrounded by a golf course. It is an easy drive to Prestonsburg. Our host was lovely, and checked on us regularly. We really could not have been more pleased. Thank you!"
United States
Leigh W.
Luxury Estate nestled atop stunning mountaintop golf course!
Cozy Home in Heart of Prestonsburg
10.0 out of 10, Exceptional, (8)
"We loved our stay at The Shotgun House! It was very clean, peaceful and safe. The bed was super comfortable, and we lacked for nothing as the host has the place fully stocked. Super easy check-in and out process. The location is perfect! You’re in town and within minutes of food, shopping and local entertainment. We will definitely stay again soon. "
United States
Tracey N.
The price is AU$273
includes taxes & fees
20 Oct - 21 Oct
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. "
United States
Glenda
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)
"Great place to stay for our family. Loved everything about the location, house, pool, and overall value."
United States
Rick S.
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace
Turkey Creek Retreats
10.0 out of 10, Exceptional, (28)
"Would stay there again."
United States
Brenda
Turkey Creek Retreats
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
Country Charm
10.0 out of 10, Exceptional, (38)
"Second time staying at the cabin. We had a blast! Awesome place to stay. "
United States
Raymond P.
Country Charm
Tiny Home on Wheels: Your Modern Escape Awaits"
2.0 star property
10.0 out of 10, Exceptional, (6)
"Had a great time at this little mountain getaway, would absolutely come back!"
United States
Dakota C.
The price is AU$196
includes taxes & fees
2 Nov - 3 Nov
Tiny Home on Wheels: Your Modern Escape Awaits"
The Red Dog Cottage In The Woods w/ Hot Tub
10.0 out of 10, Exceptional, (39)
"The nicest place iv stayed so far. Beautiful house. The hosts are very nice people. My next teip will definitely stay again."
United States
Gregory S.
The Red Dog Cottage In The Woods w/ Hot Tub
Creek View Retreat 3 Bedroom- 2 Full Bathroom. Cozy home
9.8 out of 10, Exceptional, (17)
"Great 4 wheeling from this location and a beautiful house. "
United States
Spencer G.
Creek View Retreat 3 Bedroom- 2 Full Bathroom. Cozy home
New 3 Bdrm unit w/ great location & ex. amenities
9.6 out of 10, Exceptional, (19)
"The property is in a great location in Pikeville. You can walk to several restaurants and the venue where we seen the Red Clay Strays! It was clean and spacious and just a fantastic place to stay in Pikeville, KY."
United States
Jeff
New 3 Bdrm unit w/ great location & ex. amenities
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. "
United States
Dyana F.
The Nook in Downtown Pikeville
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 :-)"
United States
Carla D.
Private Cottage Near The Lake with 3 bedrooms, 2 baths, and a gameroom!
Cozy Creekside Tiny Home w/ Full Kitchen - Walk to Distillery
The price is AU$253
includes taxes & fees
27 Oct - 28 Oct
Cozy Creekside Tiny Home w/ Full Kitchen - Walk to Distillery
Appalachian Hideaways
9.2 out of 10, Wonderful, (7)
"Great place "
United States
Bruce
Appalachian Hideaways
Trail Riders Retreat! Hatfield McCoy Trails. Private Pool. Loads of Parking!
10.0 out of 10, Exceptional, (27)
"We had a excellent time very close to trails pool is very nice house was very clean host are super nice "
United States
Seth L.
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. "
United States
eddie h.
Large 4BR Buffalo Mountain Retreat in Williamson with pool, Ride to 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!!!!👍"
United States
Lyle G.
The price is AU$236
includes taxes & fees
28 Oct - 29 Oct
Inspiration Station: Your Peaceful Getaway to Recharge and Refocus in Nature
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access
9.8 out of 10, Exceptional, (7)
"Loved the house had a great experience would definitely stay again"
United Kingdom
Gregory S.
The price is AU$459
includes taxes & fees
12 Nov - 13 Nov
Buffalo Playhouse w/ game room. Easy trail access, Direct Trail Access
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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Top Prestonsburg Hotel Reviews

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 favourite 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 depend 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 AU$196 per night. Entering your travel dates in the search wizard might find you 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 & Varia 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 & Varia 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.