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

Prestonsburg Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Prestonsburg vacation 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.
$157 nightly
The price is $178
Oct 19 - Oct 20
Total with taxes and fees
Cozy Home in Heart of Prestonsburg
A dining area with a marble table, black chairs, a potted plant, a window with a view of greenery, and a mounted TV.

2. Cozy studio on US 23 between Pikeville and Prestonsburg

Cozy studio on US 23 between Pikeville and Prestonsburg
Harold
9.6 out of 10, Exceptional, (5 reviews)
"I stayed at this place for a 2nd time on a hunting trip. Nice little place to lay your head."
United States
Jeremy
$142 nightly
The price is $157
Oct 18 - Oct 19
Total with taxes and fees
Cozy studio on US 23 between Pikeville and 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."

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.
$138 nightly
The price is $152
Oct 18 - Oct 19
Total with taxes and fees
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
9.2 out of 10, Wonderful, (10 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
$160 nightly
The price is $172
Oct 15 - Oct 16
Total with taxes and fees
Inspiration Station
A covered outdoor area with a barbecue grill and a table, overlooking a forested area.

5. 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.
$313 nightly
The price is $335
Oct 26 - Oct 27
Total with taxes and fees
Charming 2-bedroom cabin + loft in fabulous Salyersville with AC and WiFi
A wooden deck with two chairs and a red door leading to a covered area.

6. 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, (1 review)
"Very clean. Within just a few miles of attractions. Hosts were the best at communicating, and attentive to all our needs.I will recommend this to friends!"
United States
Becky M.
$119 nightly
The price is $128
Oct 19 - Oct 20
Total with taxes and fees
NO RV? NO PROBLEM! STAY IN OUR FAMILY-FRIENDLY, COZY COTTAGES.
A wooden interior with a kitchen, a sofa, a ceiling fan, and a sign reading 'Backwoods Bungalow'.

7. Backwoods Bungalow

Backwoods Bungalow
Pikeville
10.0 out of 10, Exceptional, (13 reviews)
"Worked out very nice for our stay. "
United States
Cole A.
$144 nightly
The price is $155
Oct 20 - Oct 21
Total with taxes and fees
Backwoods Bungalow
A covered deck with a grill, two chairs, and a table.

8. 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.
$134 nightly
The price is $144
Oct 15 - Oct 16
Total with taxes and fees
Modern Escape
A rustic cabin surrounded by lush greenery and a fenced area.

9. The Boons Camp Cabin

The Boons Camp Cabin
Boons Camp
$345 nightly
The price is $348
Oct 15 - Oct 16
Total with taxes and fees
The Boons Camp Cabin
A large, historic house with a prominent turret, a fountain, and a well-maintained lawn.

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

Private 2BR Renovated Guest Suite in Historic Home with Kitchen
Paintsville
$414 nightly
The price is $456
Oct 26 - Oct 27
Total with taxes and fees
Private 2BR Renovated Guest Suite in Historic Home with Kitchen
A wooden interior with two doors, a sign reading 'Wanda's Cafe,' and two woven plates on the wall.

11. 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.
$150 nightly
The price is $161
Nov 8 - Nov 9
Total with taxes and fees
Wanderers Oasis
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.
$131 nightly
The price is $146
Oct 26 - Oct 27
Total with taxes and fees
Recently Updated - Cozy Creekside Tiny Home w/ Full Kitchen; Walk to Distillery
A cozy living room with a sofa, a chair, a TV, and a fireplace.

13. 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.
$181 nightly
The price is $201
Oct 18 - Oct 19
Total with taxes and fees
Appalachian Hideaways Cabin #2
A hot tub with seating and a table, surrounded by a wooden deck and trees.

14. 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.
$296 nightly
The price is $298
Oct 15 - Oct 16
Total with taxes and fees
The Mountain Magnolia *Hot tub on private deck*
A spacious dining area with a wooden table and chairs, a kitchen in the background, and a ceiling with a grid pattern.

15. 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.
$215 nightly
The price is $239
Oct 18 - Oct 19
Total with taxes and fees
Suite 1 Trail 10 HMT
A bedroom with a wooden bed, a dresser, a mirror, and a painting on the wall.

16. Historic Cottage Near PMC, UPIKE and Arena

Historic Cottage Near PMC, UPIKE and Arena
Pikeville
$218 nightly
The price is $250
Oct 21 - Oct 22
Total with taxes and fees
Historic Cottage Near PMC, UPIKE and Arena
A wooden deck with red Adirondack chairs and a table, overlooking a town and mountains.

17. 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.
$292 nightly
The price is $325
Oct 15 - Oct 16
Total with taxes and fees
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

8/10 Good
"Norm"
Aleksei 1-night trip
Posted 4 hours ago
The Landmark Hotel

Find out more about Prestonsburg

Everything you need to know about Prestonsburg vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Prestonsburg vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Prestonsburg vacation 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 low season months. For more hustle and bustle, you may prefer to visit Prestonsburg in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $128 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Prestonsburg rentals

At Expedia, we put the best Prestonsburg vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Prestonsburg?

Yes, we have vacation rentals in Prestonsburg close to Mountain Arts Center, or you can choose 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 theaters during your trip.

What are some of the best vacation rentals in Prestonsburg?

Luxury Estate nestled atop stunning mountaintop golf course!: Visitors give good reviews to this Prestonsburg vacation home rental, which offers a patio, a garden, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection 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 vacation rentals will I find in Prestonsburg?

Expedia has 3 vacation 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 vacation rental in Prestonsburg like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Prestonsburg. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a small group gathering.