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Prestonsburg Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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.
The price is CA $138
CA $254 total
includes taxes & fees
Oct 11 - Oct 12
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
9.4 out of 10, Exceptional, (3 reviews)
"Our host stayed in good contact and the place was very cute and felt super comfortable. We were very happy with our stay :)"
United States
Lacy S.
The price is CA $96
CA $216 total
includes taxes & fees
Oct 7 - Oct 8
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.
The price is CA $96
CA $216 total
includes taxes & fees
Oct 14 - Oct 15
Cozy Tiny Home Quiet 1/1 Close to Riding Trails
A rustic cabin surrounded by lush greenery and a fenced area.

4. The Boons Camp Cabin

The Boons Camp Cabin
Boons Camp
The price is CA $86
CA $458 total
includes taxes & fees
Oct 5 - Oct 6
The Boons Camp Cabin
A covered deck with a grill, two chairs, and a table.

5. 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 CA $105
CA $205 total
includes taxes & fees
Oct 4 - Oct 5
Modern Escape
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
The price is CA $127
CA $181 total
includes taxes & fees
Oct 5 - Oct 6
NO RV? NO PROBLEM! STAY IN OUR FAMILY-FRIENDLY, COZY COTTAGES.
A wooden interior with a sofa, a blue armchair, and a potted plant.

7. 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 CA $142
CA $244 total
includes taxes & fees
Oct 7 - Oct 8
Inspiration Station
A two-story house with a porch and a staircase.

8. 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)
"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 CA $123
CA $208 total
includes taxes & fees
Oct 26 - Oct 27
Recently Updated - Cozy Creekside Tiny Home w/ Full Kitchen; Walk to Distillery
A wooden interior with a kitchen, a sofa, a ceiling fan, and a sign reading 'Backwoods Bungalow'.

9. 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 CA $183
CA $290 total
includes taxes & fees
Oct 21 - Oct 22
Backwoods Bungalow
A covered outdoor area with a barbecue grill and a table, overlooking a forested area.

10. 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 CA $178
CA $477 total
includes taxes & fees
Oct 5 - Oct 6
Charming 2-bedroom cabin + loft in fabulous Salyersville with AC and WiFi
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 CA $154
CA $282 total
includes taxes & fees
Oct 3 - Oct 4
Appalachian Hideaways Cabin #2
A hot tub with seating and a table, surrounded by a wooden deck and trees.

12. 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 CA $261
CA $423 total
includes taxes & fees
Oct 8 - Oct 9
The Mountain Magnolia *Hot tub on private deck*
A large, historic house with a prominent turret, a fountain, and a well-maintained lawn.

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

Private 2BR Renovated Guest Suite in Historic Home with Kitchen
Paintsville
The price is CA $166
CA $655 total
includes taxes & fees
Oct 26 - Oct 27
Private 2BR Renovated Guest Suite in Historic Home with Kitchen
A spacious dining area with a wooden table and chairs, a kitchen in the background, and a ceiling with a grid pattern.

14. 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 CA $178
CA $340 total
includes taxes & fees
Oct 4 - Oct 5
Suite 1 Trail 10 HMT
A wooden deck with red Adirondack chairs and a table, overlooking a town and mountains.

15. 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 CA $256
CA $462 total
includes taxes & fees
Oct 5 - Oct 6
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
"Everything"
Angela 2-night trip
Posted 14 hours ago
The Landmark Hotel

Find out more about Prestonsburg

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Prestonsburg. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.