A person sitting on a rocky outcrop overlooking a dense forested valley.

Prestonsburg Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Prestonsburg holiday rentals

A kitchen with a built-in oven, microwave, and stainless steel range.

1. Cozy Home in Heart of Prestonsburg

Cozy Home in Heart of Prestonsburg
Prestonsburg
10.0 out of 10, Exceptional, (13 reviews)
"The house was very convenient to downtown area. Everything was clean and we really enjoyed our stay. We will definitely book again on our next trip!"
United States
Ashleigh g.
The price is HK$762
HK$1,398 total
includes taxes & fees
29 Sept - 30 Sept
Cozy Home in Heart of Prestonsburg
A wooden dining table with a woven placemat, a tray with a mug and a sign saying "STAY COZY," and a small sign that reads "let it."

2. Cozy Tiny Home Quiet 1/1 Close to Riding Trails

Cozy Tiny Home Quiet 1/1 Close to Riding Trails
Martin
9.6 out of 10, Exceptional, (14 reviews)
"We found it to be a very clean, cozy, and quiet get-away!"
United States
Kimberly H.
The price is HK$529
HK$1,189 total
includes taxes & fees
27 Sept - 28 Sept
Cozy Tiny Home Quiet 1/1 Close to Riding Trails
A covered outdoor area with a barbecue grill and a table, overlooking a forested area.

3. Charming 2-bedroom cabin + loft in fabulous Salyersville with AC and WiFi

Charming 2-bedroom cabin + loft in fabulous Salyersville with AC and WiFi
Salyersville
9.8 out of 10, Exceptional, (6 reviews)
"Great host and property!"
United States
Brad M.
The price is HK$980
HK$2,645 total
includes taxes & fees
27 Sept - 28 Sept
Charming 2-bedroom cabin + loft in fabulous Salyersville with AC and WiFi
A wooden interior with a sofa, a blue armchair, and a potted plant.

4. Inspiration Station

Inspiration Station
Pikeville
9.2 out of 10, Wonderful, (9 reviews)
"Great place to stay for a solo outing or couples getaway. The road leading up to the property is pretty dicey, but the place itself was great and the host was fantastic!"
United States
John H.
The price is HK$1,247
HK$1,894 total
includes taxes & fees
21 Oct - 22 Oct
Inspiration Station
A wooden interior with a kitchen, a sofa, a ceiling fan, and a sign reading 'Backwoods Bungalow'.

5. Backwoods Bungalow

Backwoods Bungalow
Pikeville
10.0 out of 10, Exceptional, (13 reviews)
"Worked out very nice for our stay. "
United States
Cole A.
The price is HK$1,043
HK$1,623 total
includes taxes & fees
20 Oct - 21 Oct
Backwoods Bungalow
A cozy living room with a sofa, a chair, a TV, and a fireplace.

6. Appalachian Hideaways Cabin #2

Appalachian Hideaways Cabin #2
Williamson
9.4 out of 10, Exceptional, (16 reviews)
"Nice little spot to stay after a day riding the trails."
United States
Curtis J.
The price is HK$847
HK$1,579 total
includes taxes & fees
27 Sept - 28 Sept
Appalachian Hideaways Cabin #2
A covered deck with a grill, two chairs, and a table.

7. Modern Escape

Modern Escape
Pikeville
9.8 out of 10, Exceptional, (9 reviews)
"Super nice place will stay again for sure. "
United States
Rosa M.
The price is HK$722
HK$1,279 total
includes taxes & fees
27 Sept - 28 Sept
Modern Escape
A modern living room with a flat-screen TV, a sofa, a dining area with a kitchen counter, and a wooden door leading outside.

8. NO RV? NO PROBLEM! STAY IN OUR FAMILY-FRIENDLY, COZY COTTAGES.

NO RV? NO PROBLEM! STAY IN OUR FAMILY-FRIENDLY, COZY COTTAGES.
Staffordsville
The price is HK$699
HK$1,000 total
includes taxes & fees
28 Sept - 29 Sept
NO RV? NO PROBLEM! STAY IN OUR FAMILY-FRIENDLY, COZY COTTAGES.
A hot tub with seating and a table, surrounded by a wooden deck and trees.

9. The Mountain Magnolia *Hot tub on private deck*

The Mountain Magnolia *Hot tub on private deck*
Inez
10.0 out of 10, Exceptional, (5 reviews)
"Tina and Jake were excellent hosts! Loved their cozy cabin and will be back!"
United States
Gavin L.
The price is HK$1,440
HK$2,339 total
includes taxes & fees
27 Sept - 28 Sept
The Mountain Magnolia *Hot tub on private deck*
A rustic cabin surrounded by lush greenery and a fenced area.

10. The Boons Camp Cabin

The Boons Camp Cabin
Boons Camp
The price is HK$678
HK$2,730 total
includes taxes & fees
27 Sept - 28 Sept
The Boons Camp Cabin
A two-story house with a porch and a staircase.

11. Recently Updated - Cozy Creekside Tiny Home w/ Full Kitchen; Walk to Distillery

Recently Updated - Cozy Creekside Tiny Home w/ Full Kitchen; Walk to Distillery
Forest Hills
10.0 out of 10, Exceptional, (9 reviews)
"Could not have asked for a smoother check-in and out! The property is perfect for what I needed and the attention to the little details that made my stay easier (coffee pods, etc) was so appreciated!! Will stay here again when I come back to Pike Co for sure!!"
United States
Deborah C.
The price is HK$649
HK$1,116 total
includes taxes & fees
28 Sept - 29 Sept
Recently Updated - Cozy Creekside Tiny Home w/ Full Kitchen; Walk to Distillery
A wooden deck with red Adirondack chairs and a table, overlooking a town and mountains.

12. Ryder's Retreat overlooking the city of Williamson!

Ryder's Retreat overlooking the city of Williamson!
Williamson
9.2 out of 10, Wonderful, (7 reviews)
"The house was very nice. We didn’t care for the neighborhood. The people that owned the house was nice and very helpful!!! "
United States
Linda P.
The price is HK$1,412
HK$2,406 total
includes taxes & fees
28 Sept - 29 Sept
Ryder's Retreat overlooking the city of Williamson!
A spacious dining area with a wooden table and chairs, a kitchen in the background, and a ceiling with a grid pattern.

13. Suite 1 Trail 10 HMT

Suite 1 Trail 10 HMT
South Williamson
10.0 out of 10, Exceptional, (1 review)
"Great value for the accommodations. Great location. Some difficulty in getting checking information from host. Otherwise a good experience overall and would stay there again."
United States
Cammy R.
The price is HK$980
HK$1,877 total
includes taxes & fees
4 Oct - 5 Oct
Suite 1 Trail 10 HMT
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

The Landmark Hotel

The Landmark Hotel

10/10 Excellent
"Had a nice stay. Would stay again. Thank you!"
Diane 1-night trip
Posted 1 hour ago
The Landmark Hotel

Find out more about Prestonsburg

Search for holiday rentals in Prestonsburg on Expedia! You can easily find your home rentals, villas, holiday apartments in Prestonsburg using one of the methods below:

  • View our selection of featured holiday rentals in Prestonsburg
  • Use the map to find apartments and other holiday homes in the Prestonsburg neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Prestonsburg while they last

Look no further and take a look at our great range of rental properties in Prestonsburg!

Frequently asked questions

Can I find a holiday rental in Prestonsburg?

Yes, there are holiday rentals in Prestonsburg close to Mountain Arts Center, 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 & Varia Planetarium, whereas Jenny Wiley State Resort Park and Archer 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.