Holiday Rentals in Prestonsburg

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Holiday Rentals in Prestonsburg

Luxury Estate nestled atop stunning mountaintop golf course!

2.0 star property
Prestonsburg
10.0 out of 10, Exceptional, (7)
"This estate was a perfect family gathering to celebrate a milestone birthday. The host gave important information in a timely manner and the housekeeper answered questions quickly and precisely. The place is kept up and nestled in a beautiful location. Three of the family members played golf one night. Two family members enjoyed runs and the rest explored hiking. There was ample room for everyone; fun activities like ping pong and corn hole. We just had the best time and I am glad I found this...
United States
Holly T.
Luxury Estate nestled atop stunning mountaintop golf course!

Cozy Home in Heart of Prestonsburg

Prestonsburg
10.0 out of 10, Exceptional, (8)
"House is clean and decor is great. Location to town is easy and a walkable distance. Enjoyed Prestonsburg and surrounding areas. Property manager was very responsive. Great place!"
United States
Kathy B.
The price is €156
includes taxes & fees
13 Nov - 14 Nov
Cozy Home in Heart of Prestonsburg

New to the area? Stop by and see the most recent bachelor pad on the scene

Prestonsburg
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
Prestonsburg
Near Scenic Parks: Convenient Home in Prestonsburg

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

Langley
9.8 out of 10, Exceptional, (12)
"Excellent service, very friendly"
United States
Briseida S.
Kentucky's Majestic Mountaintop Estate with pool: The Bluegrass Palace

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

Williamson
9.8 out of 10, Exceptional, (17)
"House is updated and super clean. We appreciated the craftsmanship in the home and furniture as well as the tasteful decor! Place was convenient for the guys to ride their Atvs, the women to go shopping and the adult kids to claim movie day at the house❤️.Elisha was friendly and incredibly accommodating! Definitely will stay again!"
United States
Heather M.
Creek View Retreat 3 Bedroom- 2 Full Bathroom. Cozy home

Turkey Creek Retreats

Belfry
10.0 out of 10, Exceptional, (30)
"Would definitely recommend for everyone"
United States
Shawn T.
Turkey Creek Retreats

Appalachian Hideaways

Williamson
9.2 out of 10, Wonderful, (9)
"Cabin is nice and host was very nice and helpful only complaint was the train near the cabin was loud at times but would stay again."
United States
Walter G.
Appalachian Hideaways

Country Charm

Williamson
10.0 out of 10, Exceptional, (40)
"Very nice cabin"
United States
Christopher
Country Charm

The Red Dog Cottage In The Woods w/ Hot Tub

Williamson
10.0 out of 10, Exceptional, (40)
"We had the best quick two night stay at Red Dog Cottage! We loved everything about the cottage, great location, and wonderful host! Thank you again for opening up your adorable cottage to us! "
United States
Erica A.
The Red Dog Cottage In The Woods w/ Hot Tub

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

Pikeville
9.6 out of 10, Exceptional, (19)
"After staying here a year ago, I was happy to book a second stay. Our stay was great, with very pleasant communications with Amelia and a seamless arrival. We enjoyed the thoughtful updates to the property that made it even more comfortable. The property remains spotlessly clean, with comfy beds and kitchen basics supplied. We enjoyed the assortment of coffee. It was short drive to anywhere we wanted to go and we easily walked to all downtown destinations. We enjoyed meeting the family staying...
United States
Blaine S.
New 3 Bdrm unit w/ great location & ex. amenities

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

Louisa
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!

The Nook in Downtown Pikeville

Pikeville
9.0 out of 10, Wonderful, (4)
"The unit is spotless, greatly appreciate how immaculate it is. It was not explicitly stated it was on the second floor only accessible by outside stairs. Yes, the was a picture of the stairs in the listing but there was also a picture of the front of the building and several doors. I did communicate this to the owner and was told I should have known from the picture. Highly disappointed by the response. "
United States
Mary C.
The Nook in Downtown Pikeville

The Boons Camp Cabin

Boons Camp
The price is €148
includes taxes & fees
23 Nov - 24 Nov
The Boons Camp Cabin

Cozy Creekside Tiny Home w/ Full Kitchen - Walk to Distillery

Forest Hills
10.0 out of 10, Exceptional, (2)
"Sarah was an amazing host, provided absolutely anything we needed and was always available to help with anything. Loved the home and everything else."
United States
James C.
The price is €142
includes taxes & fees
13 Nov - 14 Nov
Cozy Creekside Tiny Home w/ Full Kitchen - Walk to Distillery

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

2.0 star property
Williamson
10.0 out of 10, Exceptional, (2)
"This was a very big house the slept 16 adults comfortably with rooms to spare. We had a wonderful time. We came to ride sxs in the trails. Very close to trails, gas and restaurants."
United States
Brandi F.
11 bed 7 bath large home and able to ride right from the home to the HMT trails

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

Williamson
10.0 out of 10, Exceptional, (28)
"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

Williamson
9.4 out of 10, Exceptional, (24)
"The home is beautiful and very spacious for a large group but parking gets challenging beyond 2 trucks and trailers. One neighbor was super friendly, one on the other side just kept to herself but didn’t make any fuss about our large group with trucks and trailers. The neighborhood is pretty rough in appearance but everyone we came into contact with was super nice."
United States
Justin 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
Pikeville
8.8 out of 10, Excellent, (6)
"The cabin is exactly what it looks like in the pictures. Everything appears to be brand new. It is very clean and well stocked with everything you need to enjoy your stay. There’s no cell phone signal but the Wi-Fi is strong. Josh was very responsive in communication, I will likely stay here again."
United States
Steve G.
The price is €139
includes taxes & fees
16 Nov - 17 Nov
Inspiration Station: Your Peaceful Getaway to Recharge and Refocus in Nature

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

Chattaroy
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 €247
includes taxes & fees
18 Nov - 19 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, apart-hotels, 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 €139 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 & 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.