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Vacation rentals in Pikeville

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Quick stats about vacation rentals in Pikeville

  • Total vacation rentals

    Explore 40 vacation rentals in Pikeville

  • Nightly prices starting at

    Pikeville vacation rentals start at G$6,274 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,500 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Pikeville vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Pikeville rentals

  • 4.9 Average rating

    Pikeville stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Pikeville

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost
A comfortable bedroom is present, featuring a neatly made bed covered with a light quilt. A decorative pillow adds a touch of accent. Natural light enters through a window with blinds, and a stylish light fixture illuminates the room. A nightstand with a lamp is positioned beside the bed.
Home in Pikeville
4.81 out of 5 average rating, 167 reviews

Living The Dream

*If you book for 7 days or more, you will receive a 20% discount off your stay. Our home is perfect for your visit in Pikeville, especially for a large group. Enjoy the complete home with 3 bedrooms, 2 full baths, a complete kitchen with dishwasher, & washer/dryer. You'll enjoy a good nights sleep in a quiet space on high quality mattresses. We are located just down the street from a Food City. We have free WIFI & a Smart TV (NO CABLE TV). We’re a short 5 minute drive from downtown Pikeville.

ValueFamilySleep quality

Guest favorite
Cabin in Prestonsburg
4.88 out of 5 average rating, 117 reviews

The Eagle's Rest Country Cabin

Welcome to The Eagle's Rest! This family & pet friendly cabin is nestled just outside of Prestonsburg. Mountainous escapes of sunrises & sunsets. Enjoy family time w/a game room featuring a bar, billiard table, & dart board. Garage w/fire pit for entertaining or a small RV/Camper! Smart-Tv’s w/YouTubeTV & T-Mobile Int. Located near StoneCrest Golf Course. Put on your hiking boots for Jenny Wiley State Park, & Sugarcamp Mtn.Trails & Middle Creek Battlefield. Mountainous air & bird watching await.

FamilyLocationBathroom

Top guest favorite
A spacious living and dining area features a wooden dining table surrounded by six chairs. A comfortable sofa and two armchairs are arranged for relaxation. Natural light streams in through large windows, highlighting the country-themed decor and the welcoming ambiance of the room.
Cabin in Williamson
4.98 out of 5 average rating, 46 reviews

Trail Riders Retreat with private in-ground pool

If you’re looking for a place to relax and unwind on either a huge front porch or a cool, cozy secluded back porch after a long day on the Hatfield – McCoy Trails, you’ve found the perfect place. With a constant cool, mountain breeze and the sounds of nature, you’re sure to enjoy your stay here at Trail Riders Retreat located in Lick Creek, Williamson, WV. This house is conveniently located within 3.5 miles of shopping and dining and is approximately 1.5 miles from #26 trail entrance. Pool Open!

FamilyLocationCheckout

Guest favorite
The exterior of a wooden home is showcased, featuring a covered front porch with steps leading up to it. A gravel pathway and a welcoming sign are visible, surrounded by greenery. Large windows allow natural light into the space.
Cabin in Martin
4.96 out of 5 average rating, 48 reviews

Cecelia Ann Tiny Home 1/1 Quiet

Kick back and relax in this calm, stylish space. Quiet area Boho vibes, home was completed in November 2023 all new furnishings, complete kitchen, inside washer and dryer. All appliances, Keurig coffee pot for either single cup or entire pot. Covered front porch, off street parking. Close to several area hospitals, 16 miles to Pikeville and Appalachian Wireless Arena. Close to riding trails for 4 wheelers or side by sides. Less than 2 hours from casino, little over hour away from Red River Gorg

LocationFamilyLaundry

Guest favorite
Home in Elkhorn City
4.85 out of 5 average rating, 266 reviews

The Alma Potter House

Family friendly, small fenced in area. 2 BR/bath upstairs, 2 BR/bath downstairs. large living/dining room. Rural, white water rafting, near Breaks Interstate Park, Pine Mountain Trail, Hillbilly Days, Hatfields & McCoys. Be in Norton/Wise, Grundy, VA, Pikeville, KY or Williamson WV in minutes. FB: Breaks Interstate Park, Hillbilly Trail System, City of Elkhorn City Events, Southern Gap Adventure Trails, Arts Collaborative Theatre Inc., KY Whitewater Rafting. Pike Co Tourism webpage.

FamilyValueNearby

Guest favorite
Apartment in McDowell
5.0 out of 5 average rating, 19 reviews

Tranquil 2-bedroom apartment

Consider this lovely apartment your home away from home while you visit McDowell. With queen beds in the 2 bedrooms and a cozy living room with a futon, there's plenty of space for guests to relax, including a front porch. Enjoy the beautiful bathtub in the bathroom and take advantage of amenities like heating, AC, Wi-Fi, and a washing machine. A welcoming retreat in the heart of the city, this apartment is a great place to call home base while you're away. We hope you enjoy your stay.

ValueLocationBathroom

Top guest favorite
The cottage stands nestled among trees, with a welcoming exterior illuminated by soft lighting at dusk. A well-kept walkway leads to double glass doors framed by inviting outdoor seating areas, creating an accessible entry point to the home.
Place to stay in Williamson
4.98 out of 5 average rating, 127 reviews

The Red Dog Cottage In The Woods w/ Hot Tub

Private parking with a 30ft covered walking bridge overlooking a water stream to lead you to the cottage. Queen bedroom downstairs; spiral staircase takes you to your loft queen bedroom; one full bath; full kitchen; TV/WIFI; indoor loft hammock; wrap around covered porch; tree covered outdoor shower area with covered hot tub; covered dining back porch. Large fire pit area with dried fire wood. Large 12ft x 12ft outdoor hammock behind fire pit. Park Series charcoal grill outside.

ValueLocationHot tub

Guest favorite
A welcoming front porch features two black rocking chairs positioned on a tiled floor. A decorative front door is framed by two glass lanterns on each side. The ceiling is adorned with detailed molding, and dark shutters complement the windows flanking the entrance.
Home in Pikeville
4.87 out of 5 average rating, 89 reviews

Mountain view country home

This stylish place to stay is perfect for group trips. This cozy country home is nestled on a hill, just walking distance from downtown Pikeville and the hospital. Lots of privacy with beautiful mountain views from a big front porch and a soothing waterfall can be seen after a nice rain from the upstairs screened in porch. Great for large groups or families. Walking distance to Appalachian wireless arena, UPIKE,Med ,Optometry, Nursing Schools, and Pikeville Medical Center.

ValueLocationParking

Top guest favorite
A cozy living area features warm wooden walls and a gray sofa, complemented by decorative pillows. A blue accent chair adds a pop of color, while a large plant brings a touch of nature indoors. Light streams in from a skylight above.
Cabin in Pikeville
5.0 out of 5 average rating, 43 reviews

Inspiration Station

Inspiration Station at Harvey's Hideaway Haven is designed to uplift your spirit and ignite your inner drive. You will be immersed in nature, surrounded by the beauty of the wilderness. While this offers a peaceful escape, please be aware that you may encounter local wildlife, including bugs, bees, and other creatures that share this natural setting. Located just 9 miles from Pikeville Medical Center, Upike and The Appalachian Wireless arena!

LocationFamilyKitchen

Superhost
Apartment in Pikeville
4.85 out of 5 average rating, 13 reviews

The Loft at Caney Creek

Welcome to your newly renovated, cozy 2nd-floor studio . This comfortable hideaway offers the perfect blend of relaxation and convenience, making it ideal for travelers, trail riders, workers, and weekend explorers. Prime location right off US Hwy 23 South — just 15 minutes from Pikeville for dining, shopping, events, and hospitals and only 2 miles from the Hillbilly Hills trail entrance in Dorton, KY.

LocationFamilyBathroom

Superhost
The living area features a sectional sofa adorned with decorative pillows, positioned near a wooden coffee table. Natural light enters through a large window, highlighting the exposed wooden beams and rustic décor. A dining area with a wooden table and chairs is visible in the background.
Cabin in Pikeville
4.92 out of 5 average rating, 37 reviews

Coal Miner’s Daughter Cabin | Boutique Hotel Suite

A premier property for travelers and locals seeking an authentic Appalachian experience; guests are immersed in rustic textiles, art inspired by nature, and nostalgic nods to favorite household goods from times past in this fully furnished unit; we celebrate the appalachian outdoors through a mashup of summer camp and ski lodge theming year round.

ValueLocationBathroom

Guest favorite
A grand facade of the home is showcased under a clear blue sky, featuring a large arched entrance framed by elegant landscaping. A decorative bronze fountain stands prominently in the foreground, surrounded by a neatly paved driveway that leads to the entrance.
Home in Prestonsburg
5.0 out of 5 average rating, 17 reviews

Mountain Manor Luxury Estate

Our fabulous Mountaintop get-away (now under new management) is nestled on nearly 2 acres atop Stonecrest Golf Course. This sprawling property is perfect for family gatherings, receptions, bonding retreats, and more – we’ve even had weddings!

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Popular amenities for Pikeville vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Pikeville

Top guest favorite
Cabin in Breaks
4.92 out of 5 average rating, 78 reviews

Hit the Breaks Cabin - Ideal Location with a View!

LocationValueRiver

Top guest favorite
The exterior of a charming end unit townhome is shown, featuring a combination of brick and wood paneling. A welcoming front door is adorned with seasonal decorations. Flanking the door, two chairs with decorative cushions provide a cozy spot for relaxation. Pathway and landscaping enhance the inviting entrance.
Townhouse in Pikeville
4.99 out of 5 average rating, 87 reviews

Brick and Stone on Cedar Creek

LocationValueNearby

Guest favorite
Home in Pikeville
5.0 out of 5 average rating, 6 reviews

Bowling Rentals - Pine Fork Lodging

LocationCleanlinessQuiet

A two-story home with a combination of brick and stone exterior is positioned on a gently sloping lawn. A paved driveway leads to a two-car garage, and a covered porch extends across the front of the house, offering outdoor seating options.
Home in Pikeville
4.83 out of 5 average rating, 24 reviews

Home Place at Pikeville

LocationFamilyOutdoor spaces

Guest favorite
Tiny home in Pikeville
4.91 out of 5 average rating, 11 reviews

Cozy on Caney

LocationWifiCleanliness

Home in Pikeville
4.8 out of 5 average rating, 5 reviews

Valley View Retreat - Unit 2

LocationNearbyParking

Home in Virgie
5.0 out of 5 average rating, 3 reviews

The Hampton House - Virgie

HospitalityCleanliness

A spacious bed is centered against a wall, featuring a dark headboard and layered with an assortment of pillows. Nightstands with decorative lamps sit on either side, complemented by small vases of flowers. A remote control rests on the bedspread.
Home in Pikeville
4.69 out of 5 average rating, 54 reviews

Entire Private Home ☆ Pikeville Ky☆ 6 min to Expo

ValueLocationParking

When is the best time to visit Pikeville?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$21,124 GYDG$21,960 GYDG$20,706 GYDG$24,470 GYDG$23,634 GYDG$24,888 GYDG$22,379 GYDG$22,797 GYDG$23,215 GYDG$20,915 GYDG$20,915 GYDG$22,797 GYD
Avg. temp2°C4°C9°C15°C19°C23°C24°C24°C21°C15°C9°C4°C

Frequently Asked Questions

  • What are the best places to stay in Pikeville?

    Stays are frequently suggested around the downtown area, which has easy access to restaurants, shops, and cultural sites. The neighborhoods near city parks or the riverfront also welcome guests seeking a quieter setting.

  • What are the best things to do in Pikeville with kids?

    Kids can explore playgrounds and picnic areas at Pikeville City Park, learn about local history at the Big Sandy Heritage Center Museum, and take part in outdoor activities during area festivals. Family-owned restaurants and ice cream shops around town are also frequently suggested for treats.

  • What are some of the best things to do in Pikeville?

    Pikeville has a walkable historic downtown, the Big Sandy Heritage Center Museum for cultural exhibits, and parks for hiking or picnicking. Many visitors enjoy browsing local shops, sampling regional food, and attending community events.

  • How is the weather in Pikeville?

    Pikeville has mild winters around 28–44°F (-3–7°C) with some rainfall, and warmer, humid summers near 67–85°F (19–29°C). Spring and autumn are often recommended for comfortable temperatures and vibrant mountain scenery.

  • When is the best time to visit Pikeville?

    Late spring and early autumn are often recommended for milder temperatures, blooming landscapes, and local festivals. Summer brings outdoor events and music, while winter is quieter with occasional snow and cooler days.

  • What are the best places to visit in Pikeville?

    Explore the Big Sandy Heritage Center Museum for exhibits on Appalachian and regional history, stroll through historic downtown Pikeville, and unwind in Pikeville City Park. Riverfront spaces and public art highlight the area's traditions.

  • What are some hiking trails in Pikeville?

    Explore the trails at Pikeville City Park, follow forested routes around Fishtrap Lake, and wander paths in the surrounding Appalachian hills. These spots frequently suggested for hiking offer a mix of natural viewpoints and woodland walks.

  • What are some family activities we can do in Pikeville?

    Families often enjoy Pikeville City Park for playgrounds and walking trails, or discovering regional stories at the Big Sandy Heritage Center Museum. Seasonal festivals and local fairs bring additional activities for all ages.

  • What are some of the best day trip ideas from Pikeville?

    Consider visiting scenic natural areas, exploring cultural attractions in nearby communities, or discovering Appalachian craft shops and heritage centers. Many travelers seek out local parks, historic sites, and mountain overlooks for day trips.

  • Are there any pet friendly accommodations available in Pikeville?

    Many accommodations around Pikeville welcome pets, especially in neighborhoods near city parks and outdoor spaces. Some stays frequently suggested have convenient access to walking trails and grassy areas.

  • What are some local tips for visiting Pikeville?

    Greet locals warmly, pack comfortable footwear for hilly streets, and try regional foods. Attend a festival or community event for authentic Appalachian culture, and explore beyond downtown for quieter nature spots.

  • What is Pikeville known for?

    Pikeville is known for its Appalachian heritage, vibrant festivals, and historic downtown. The city has a strong tradition of music, regional cuisine, and storytelling rooted in the mountain communities.

  • What are the best hidden gems to explore in Pikeville?

    Discover locally rooted artisan studios, quiet walking paths along the Levisa Fork, and lesser-known cultural exhibits in smaller museums. The area is known for friendly coffee shops, overlooked murals, and peaceful riverfront spots.

  • What are the best foods to try in Pikeville?

    Try Appalachian staples such as cornbread, country ham, and locally made jams. Pikeville has barbecue, regional desserts, and homestyle dishes influenced by mountain traditions.

  • What should I bring for a trip to Pikeville?

    Bring layered clothing for changing temperatures, sturdy walking shoes for exploring parks or downtown, and a rain jacket due to the region's rainfall. A camera and reusable water bottle are also handy for scenic outings.

  • What is the nightlife in Pikeville like?

    Nightlife in Pikeville centers around local bars, live music venues, and downtown eateries. Some spots feature bluegrass bands, while others provide laid-back spaces for food and conversation.

  • What are the most popular events or festivals in Pikeville?

    Pikeville has events that draw locals and visitors, including Hillbilly Days in spring, which celebrates Appalachian culture with food, music, and crafts. The area frequently hosts fairs, heritage festivals, and seasonal concerts in city parks.

  • Are there family friendly vacation rentals in Pikeville?

    Many vacation rentals in Pikeville accommodate families, especially near downtown and the city park area. These stays have amenities for group gatherings, kitchens, and comfortable spaces for kids.