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Prestonsburg Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

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, (14 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 AU$243
includes taxes & fees
4 Nov - 5 Nov
Cozy Home in Heart of Prestonsburg
A wooden deck overlooking a river with dense greenery and trees.

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

NO RV? NO PROBLEM! STAY IN OUR FAMILY-FRIENDLY, COZY COTTAGES.
Staffordsville
10.0 out of 10, Exceptional, (2 reviews)
"I booked this for my parents coming from Florida and the hosts were amazing, the place was perfectly clean, and they were excellent with communication!!! VERY HIGHLY RECOMMEND!!! Would 1,000% stay again!!!"
United States
Andrew
The price is AU$160
includes taxes & fees
5 Nov - 6 Nov
NO RV? NO PROBLEM! STAY IN OUR FAMILY-FRIENDLY, COZY COTTAGES.
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."

3. 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 AU$194
includes taxes & fees
8 Nov - 9 Nov
Cozy Tiny Home Quiet 1/1 Close to Riding Trails
A wooden interior with a sofa, a blue armchair, and a potted plant.

4. Inspiration Station

Inspiration Station
Pikeville
9.4 out of 10, Exceptional, (11 reviews)
"Everything was wonderful. It was peaceful and quiet. We loved the resident cat. Just a beautiful cabin and beautiful place! We will stay down here anytime we come to visit in the area."
United States
Susan
The price is AU$234
includes taxes & fees
4 Nov - 5 Nov
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 AU$210
includes taxes & fees
4 Nov - 5 Nov
Backwoods Bungalow
A covered deck with a grill, two chairs, and a table.

6. Modern Escape

Modern Escape
Pikeville
9.8 out of 10, Exceptional, (9 reviews)
"Nice and cozy , we had a great time while in the area . Nice amenities for the price, was a wonderful stay. Thanks to the host for having us"
United States
Morris D.
The price is AU$194
includes taxes & fees
4 Nov - 5 Nov
Modern Escape
A rustic cabin surrounded by lush greenery and a fenced area.

7. The Boons Camp Cabin

The Boons Camp Cabin
Boons Camp
The price is AU$486
includes taxes & fees
8 Nov - 9 Nov
The Boons Camp Cabin
A covered outdoor area with a barbecue grill and a table, overlooking a forested area.

8. 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, (7 reviews)
"Great host and property!"
United States
Brad M.
The price is AU$447
includes taxes & fees
30 Nov - 1 Dec
Charming 2-bedroom cabin + loft in fabulous Salyersville with AC and WiFi
A wooden deck with outdoor furniture, including chairs and a table, and a white building with a window and door.

9. Tranquil 2-bedroom apartment in McDowell with AC, WiFi

Tranquil 2-bedroom apartment in McDowell with AC, WiFi
McDowell
The price is AU$194
includes taxes & fees
4 Nov - 5 Nov
Tranquil 2-bedroom apartment in McDowell with AC, WiFi
A wooden interior with two doors, a sign reading 'Wanda's Cafe,' and two woven plates on the wall.

10. Wanderers Oasis

Wanderers Oasis
Pikeville
10.0 out of 10, Exceptional, (1 review)
"Very quaint and quiet. Nice relaxing evening in the woods and mountains."
United States
Paul F.
The price is AU$218
includes taxes & fees
15 Nov - 16 Nov
Wanderers Oasis
A cozy living room with a sofa, a chair, a TV, and a fireplace.

11. 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 AU$274
includes taxes & fees
4 Nov - 5 Nov
Appalachian Hideaways Cabin #2
A two-story house with a porch and a staircase.

12. 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
9.8 out of 10, Exceptional, (10 reviews)
"It was a peaceful and quiet place. Very clean and tidy. Has it's own driveway to park. The host was amazing, nice and very responsive."
United States
deborah j.
The price is AU$203
includes taxes & fees
2 Dec - 3 Dec
Recently Updated - Cozy Creekside Tiny Home w/ Full Kitchen; Walk to Distillery
A wooden cabin with a porch, a dog, and a person sitting on a swing.

13. Historic Cottage Near PMC, UPIKE and Arena

Historic Cottage Near PMC, UPIKE and Arena
Pikeville
10.0 out of 10, Exceptional, (1 review)
"Beautiful little cottage! We absolutely loved the decor and the historic artifacts with accompanying literature! Fav part by far is the bunkbeds and LED lighting with historic copies of newspaper articles. Very close to town! We would definitely return!"
United States
Jamie V.
The price is AU$310
includes taxes & fees
15 Nov - 16 Nov
Historic Cottage Near PMC, UPIKE and Arena
A large, historic house with a prominent turret, a fountain, and a well-maintained lawn.

14. Private 2BR Renovated Guest Suite in Historic Home with Kitchen

Private 2BR Renovated Guest Suite in Historic Home with Kitchen
Paintsville
The price is AU$598
includes taxes & fees
8 Nov - 9 Nov
Private 2BR Renovated Guest Suite in Historic Home with Kitchen
A hot tub with seating and a table, surrounded by a wooden deck and trees.

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

The Mountain Magnolia *Hot tub on private deck*
Inez
10.0 out of 10, Exceptional, (6 reviews)
"Tina and Jake were excellent hosts! Loved their cozy cabin and will be back!"
United States
Gavin L.
The price is AU$406
includes taxes & fees
4 Nov - 5 Nov
The Mountain Magnolia *Hot tub on private deck*
A wooden deck with red Adirondack chairs and a table, overlooking a town and mountains.

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

Ryder's Retreat overlooking the city of Williamson!
Williamson
8.6 out of 10, Excellent, (8 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 AU$595
includes taxes & fees
4 Nov - 5 Nov
Ryder's Retreat overlooking the city of Williamson!
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
"Good one night stay while in Pikeville, KY."
Karen 1-night trip
Posted 2 hours ago
The Landmark Hotel

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$160 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 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 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.