Prestonsburg vacation rentals

We found 19 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Prestonsburg that are perfect for your trip. Whether you're going on vacation with family or friends, vacation rentals have the best amenities for spending time at your vacation home, which might include WiFi and a fireplace. You'll be sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

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Find out more about Prestonsburg

Why visit Prestonsburg

  • Stunning Outdoor Scenery: Prestonsburg offers breathtaking views, particularly in the Prestonsburg Range and nearby lakefront towns, perfect for hiking and exploration.
  • Rich Cultural Experience: Visitors can immerse themselves in local art at the arts center and discover fascinating exhibits at the science museum.
  • Family-Friendly Activities: With a variety of attractions suitable for all ages, Prestonsburg is an ideal destination for family adventures.
  • Diverse Accommodations: From cozy cabins to spacious homes, there are plenty of lodging options to fit every budget.
  • Welcoming Community: Experience the charm of a friendly town where hospitality is a priority, making your stay memorable.

Popular types of accommodation in Prestonsburg

Explore our diverse selection of vacation rentals in Prestonsburg, where you'll find charming cabins, spacious private homes, and cozy apartments. Whether you're seeking budget-friendly options or looking for comfortable bedroom apartments, Prestonsburg has something for everyone. Popular locations like Poplar St. offer easy access to local attractions. Choose the perfect accommodation that fits your travel needs and enjoy a memorable stay in this welcoming community.

  • Cabins: The top choice for travelers seeking a cozy escape, cabins in Prestonsburg offer a rustic charm and a connection to nature.
  • Houses: Ideal for families or groups, these fully-equipped homes provide privacy and all the comforts of home during your stay.
  • Apartments: A convenient option for solo travelers or couples, apartments in Prestonsburg offer a comfortable and compact living space.
  • Cottages: Quaint and inviting, cottages provide a charming retreat for those looking to relax in a picturesque setting.**

Top attractions in and around Prestonsburg

Prestonsburg, Kentucky, is an ideal destination for outdoor enthusiasts and adventure seekers, offering stunning scenery and a rich cultural experience. Visitors can explore historic sites, enjoy local art at the arts center, or discover fascinating exhibits at the science museum. This charming town provides a variety of attractions that cater to families and those looking for outdoor fun, making it a perfect spot for a memorable vacation.

  • Loretta Lynn's Birthplace - Butcher Hollow: Discover the humble beginnings of country music legend Loretta Lynn in this historic house, located 8 miles from Prestonsburg. Experience the rich cultural heritage and the beautiful Appalachian landscape that inspired her music.
  • Mountain Arts Center: Nestled in Prestonsburg, this vibrant arts center showcases a variety of local talent through performances and art exhibitions, fostering a strong sense of community and culture.
  • East Kentucky Science Center and Planetarium: Located in Prestonsburg, this interactive science museum offers engaging exhibits and a planetarium, making it a perfect destination for families and education enthusiasts alike.

Things to do recommended for couples

For a romantic getaway in Prestonsburg, enjoy a scenic hike at the nearby Jenny Wiley State Resort Park or take a peaceful paddleboat ride on Dewey Lake. Don't miss a candlelit dinner at a local restaurant to savor the flavors of Kentucky together.

Things to do recommended for families

Your family will love the Knott County Sportsplex, a recreation park just 19 miles from Prestonsburg. With its wellness and relaxation vibes, it's the perfect spot for outdoor activities and family fun, ensuring a memorable experience for all ages.

Things to do recommended for groups

Enjoy a round of golf at StoneCrest Golf Course or Paintsville Golf Course for some outdoor fun. For a bit of adventure, hike the Swamp Branch Trailhead, located 9 miles from Prestonsburg, where you can soak in beautiful scenery while bonding with your group.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Prestonsburg

If you're traveling with friends, family, pets, or planning an extended stay, be sure to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips just for you.

  • Traveling to Prestonsburg with a group: Think about how many bedrooms you require, as well as features like a full kitchen or outdoor space for group gatherings. Fortunately, on Vrbo, you can easily filter for these options and much more.
  • Traveling to Prestonsburg with young kids: Traveling with little ones can be quite an adventure. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, think about how close you are to family-friendly attractions to enhance your experience.
  • Taking your pets with you to Prestonsburg: For many families, a vacation just isn’t the same without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Prestonsburg: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can easily discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Prestonsburg

Prestonsburg, Kentucky, is a hidden gem for outdoor enthusiasts and adventure seekers. You can explore the stunning Prestonsburg Range and enjoy the scenic beauty of nearby lakefront towns. This family-friendly destination offers a unique blend of budget and luxury experiences, making it perfect for all types of travelers. Whether you're hiking the trails or enjoying local attractions, your vacation in and around Prestonsburg promises unforgettable moments and breathtaking scenery.

  • Paintsville: Located 10 miles from Prestonsburg, Paintsville is a charming city that offers an outdoor adventure experience amidst beautiful scenery. Nature enthusiasts will appreciate the recreational areas and hiking trails that beckon exploration. Popular venues include the local recreation center, where you can engage in various activities. Don't miss visiting the nearby national state park, a serene lake, and well-maintained parks that provide perfect spots for picnicking or relaxation.
  • Dwale: Just 4 miles away from Prestonsburg, Dwale is a city primarily known for its business-themed atmosphere. While it may not have the extensive recreational options found in neighboring areas, it serves as a convenient hub for those traveling for work or business purposes. Its proximity to Prestonsburg makes it an ideal location for quick trips, meetings, and networking opportunities.
  • Martin: Situated 6 miles from Prestonsburg, Martin is a delightful city that caters to outdoor lovers and families seeking eco-friendly experiences. You'll find a variety of attractions such as resorts, recreational areas, and campgrounds perfect for a weekend getaway. The local parks and lakes provide stunning natural settings for family outings, while the nearby national state park invites those looking to immerse themselves in the great outdoors. Martin is an excellent choice for those wanting to connect with nature while enjoying quality time with loved ones.

Best time to go to Prestonsburg

If you're planning a trip to Prestonsburg, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and October, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January34.7°F (1.5°C)Light RainMostly CloudyModerately LowAverage
February38.8°F (3.8°C)Light RainMostly CloudyModerately LowSlightly Low
March46.9°F (8.3°C)Light RainMostly CloudyAverageSlightly Low
April56.3°F (13.5°C)Light RainMostly SunnyAverageAverage
May65.3°F (18.5°C)Light RainMostly SunnyAverageAverage
June72.7°F (22.6°C)Light RainMostly SunnyModerately HighSlightly High
July75.9°F (24.4°C)Light RainMostly SunnyModerately HighSlightly High
August74.3°F (23.5°C)Light RainMostly SunnyAverageAverage
September68.7°F (20.4°C)Light RainMostly SunnyAverageAverage
October58.1°F (14.5°C)Light RainMostly SunnyModerately HighSlightly Low
November46.8°F (8.2°C)Light RainMostly SunnyAverageAverage
December40.5°F (4.7°C)Light RainMostly CloudyModerately LowSlightly High

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to narrow your search by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a user-friendly platform for planning your travels. Whether you're looking to create new trips, continue from where you last stopped, or organize your existing plans, it’s all in one place. You can easily find the properties you’ve saved or booked, sorted into categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Travel to lively Prestonsburg

Enjoy the area's live music, theater scene and opera and make a vacation rental your home during your stay in Prestonsburg. Renowned for its riverfront, hiking and mountain views, this city welcomes all visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Prestonsburg

Are you hoping to discover attractions to visit while you're in town? Venture out of your cozy vacation rental and experience everything that Prestonsburg has to offer. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • StoneCrest Golf Course (1.9 mi / 3 km)
  • Paintsville Golf Course (9.9 mi / 15.9 km)

Exploring the natural landscape of Prestonsburg

Whether you're looking for fun outdoor activities or just want to take in the scenery, Prestonsburg is a great spot to appreciate mother nature. These are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Archer Park (0.7 mi / 1.1 km)
  • Jenny Wiley State Resort Park (3.1 mi / 5 km)
  • Swamp Branch Trailhead (8.9 mi / 14.3 km)
  • Paintsville Lake State Park (13.4 mi / 21.6 km)
  • Middle Creek National Battlefield (2.5 mi / 4 km)
  • Paintsville Lake (16.9 mi / 27.2 km)

How to get to and around Prestonsburg

Fly into Pikeville, KY (PVL-Pike County - Hatcher Field), the closest airport, located 13.5 mi (21.8 km) from the city center.

Frequently asked questions

What is the best area to stay in Prestonsburg, Kentucky, United States of America when booking a vacation rental?
When considering the best area to stay in Prestonsburg, Kentucky, one highly recommended neighborhood is the downtown area. This vibrant locale is not only picturesque but also conveniently located near several attractions that showcase the charm of the region. Visitors can explore the historic music scene at the Country Music Highway, which celebrates the rich cultural heritage of country music artists from the area. Additionally, the nearby Jenny Wiley State Resort Park offers beautiful natural landscapes, hiking trails, and opportunities for outdoor recreation, making it a great spot for nature enthusiasts.

Another appealing area is the vicinity of the Prestonsburg Cultural Arts Center. This neighborhood boasts a variety of local dining options and shops, immersing you in the community's lively option. The arts center regularly hosts events and performances, adding to the cultural experience of your stay.
How much does it cost to rent a vacation home in Prestonsburg?
Prices for vacation rentals in Prestonsburg vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Prestonsburg to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Prestonsburg vacation house rentals?
You can find great discounts on house rentals in Prestonsburg on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Prestonsburg?
In Prestonsburg, vacation houses are quite popular, alongside several condos, cottages, and apartments available throughout the area. These accommodations tend to be located in peaceful neighborhoods, providing a relaxed atmosphere for travelers. Most vacation houses feature multiple bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or groups. Condos and apartments often include modern amenities such as Wi-Fi, laundry facilities, and sometimes access to communal pools or fitness centers.
Are there any family house rentals in Prestonsburg?
In Prestonsburg, Kentucky, there are some family-friendly house rentals available, making it a great spot for groups looking to enjoy the natural beauty of the area. Many of these homes come equipped with spacious living areas, full kitchens for preparing family meals, and outdoor spaces where children can play.

The town is close to attractions like the Jenny Wiley State Resort Park, where visitors can enjoy hiking, fishing, and outdoor activities. Additionally, the vibrant local community often hosts events and festivals that families can enjoy together.
Can I find long-stay vacation rentals in Prestonsburg?
A long-stay vacation rental in Prestonsburg is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Prestonsburg?
In Prestonsburg, travelers can find several pet-friendly house rentals that cater to both comfort and convenience. Many of these homes are equipped with modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy some fresh air. The area offers a welcoming environment for pet owners, with easy access to local parks and trails for walking and outdoor activities.

While enjoying your stay, visitors can explore the scenic beauty of the surrounding Appalachian region, which provides opportunities for hiking and enjoying nature. The town itself features charming local shops and dining options, making it a comfortable base for your adventures with your furry friends.
Are there any remote work vacation rentals in Prestonsburg?
In Prestonsburg, Kentucky, there are several remote work vacation rentals available that cater to travelers needing a productive environment. Many of these properties are equipped with essential amenities such as high-speed internet, designated desk spaces, and Wi-Fi in the rooms, allowing for a comfortable work setting. Additionally, some rentals permit events, making them suitable for small gatherings or meetings. The area's natural beauty and proximity to attractions like the Jenny Wiley State Resort Park provide great opportunities for relaxation after work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Prestonsburg vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Prestonsburg with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Prestonsburg?
In Prestonsburg, popular rental amenities include kitchens, which allow travelers to prepare their own meals, and air conditioning for comfort during the warmer months. Many rentals also come equipped with blenders and coffee/tea makers, making it easy to enjoy morning beverages or quick snacks. Additionally, having a desk in some of these properties provides a convenient workspace for those who may need to catch up on tasks while away.
How early should I book a Prestonsburg vacation rental?
Book your Prestonsburg vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Prestonsburg, Kentucky, United States of America?
In Prestonsburg, Kentucky, visitors can explore a range of attractions that highlight the area's rich history and natural beauty. The Mountain Arts Center is a major draw, featuring performances and exhibits that celebrate Appalachian culture and music. It's a great spot for those interested in local arts.

For outdoor enthusiasts, the nearby Jenny Wiley State Resort Park offers hiking trails, fishing, and scenic views of Dewey Lake, making it an ideal destination for nature lovers. The park also features cabins and lodges, providing convenient access to recreational activities.

Another top site is the Prestonsburg Battlefield State Historic Site, where visitors can learn about Civil War history and enjoy walking trails that weave through the picturesque landscape.
Can I change or cancel my Prestonsburg home rental booking on Vrbo?
To find Prestonsburg vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Prestonsburg vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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