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Vacation rentals in Pikeville

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Top-rated vacation rentals in Pikeville

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Top guest favourite
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
4.97 out of 5 average rating, 36 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

Guest favourite
The kitchen features a spacious island with four cushioned stools, modern pendant lighting, and a distinctive SMEG fridge. Clean countertops offer ample prep space, while stylish green tile backsplashes add a chic touch. The area is well-lit and flows seamlessly into the living space.
Apartment in Pikeville
4.93 out of 5 average rating, 135 reviews

Walk to dinner, UPIKE, hospital•3 Lux Bed• Balcony

Upstairs-The Eccentric Privy is the best of the best worlds. Retro, glam & quirky! You’ll obsess over the thought put into each room & even get some inspiration. Extra amenities include… Outdoor deck Quartz Countertops Luxury tile SMEG fridge Smart thermostat Bathroom Bluetooth speaker USB outlet in each room Soft close doors & drawers in kitchen & bathroom 550 TC cotton bed sheets and pillow covers Allergy defense, antimocrobial pillow protectors Tankless water heater for endless hot water

Guest favourite
Home in Elkhorn City
4.84 out of 5 average rating, 257 reviews

The Alma Potter House

Family friendly, small fenced in area. Two bedrooms/bath upstairs, 2 bedrooms/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 pages: Breaks Interstate Park, City of Elkhorn City Events, Southern Gap Adventure Trails, Arts Collaborative Theatre Inc., Kentucky Whitewater Rafting. Pike Co Tourism webpage.

Superhost
The exterior of the chalet features a two-story structure surrounded by lush greenery. A covered porch extends from the second level, and a staircase leads down to the landscaped yard. Pathways and railings create a welcoming access to the home.
Treehouse in Williamson
4.97 out of 5 average rating, 121 reviews

The Red Dog Chalet Couples Retreat w/ Hot Tub

Trailer access pull-thru private parking area with a beautiful lighted walking bridge that leads you to the chalet. A beautiful getaway with a spiral staircase leading you to the 2nd story covered porch with a wraparound walking deck. Large firepit area with dried fire wood. Large 12ft by 12ft hammock beside fire pit area. Two person copper tub; private outdoor shower; hot tub and large bed swing. Loft bedroom. Free WIFI. Park Series charcoal grill outside. Buffalo Mt trailhead 1/2 mile.

Guest favourite
A cozy living area includes a neutral-colored sofa with turquoise accent pillows and a soft area rug. Natural light enters through two windows with floral valances, illuminating the space. A small dining table with white chairs is visible in the background, enhancing comfort and functionality.
Tiny homes in Forest Hills
4.81 out of 5 average rating, 37 reviews

New Paint & Flooring - Cozy Creekside Tiny Home

Little Cottage offers a comfortable space for a quick visit or a lingering stay to explore everything in the community from riding the Hatfield-McCoy Trails, fishing the Tug River, hiking to the West Virginia swing, or some peace and quiet in a safe and friendly neighborhood. Conveniently located near shopping, restaurants and just a few miles from a trailhead. Plan a visit to Pauley Hollow Distillery less than a half a mile from Little Cottage for real moonshine and Kentucky bourbon!

Guest favourite
The kitchen area features wooden cabinetry and a long countertop with a sink and microwave. A two-burner stovetop is present, alongside a toaster and a coffee maker. Shelves display various utensils and glassware, while a trash can and high stool are positioned nearby.
Cabin in Pikeville
5 out of 5 average rating, 7 reviews

Wanderer’s Oasis

Wanderer's Oasis at Harvey's Hideaway Haven is a Boho-themed studio cabin retreat that features a Queen size bed! (280 sq ft of living space) 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, frogs and other creatures that share this natural setting. Located just 9 miles from Pikeville Medical Center, Upike and The Appalachian Wireless arena!

Top guest favourite
A spacious living area features a comfortable brown leather sofa and a circular chair. A 58" TV is mounted on the wall, accompanied by a wooden entertainment unit. Natural light filters through sheer curtains, and decorative artwork is displayed on the walls.
Home in Prestonsburg
4.96 out of 5 average rating, 134 reviews

The Shotgun House

Enjoy your stay at the Shotgun house located in the heart of Prestonsburg within walking distance to a popular restaurant and downtown shopping. This cozy house offers a 58" TV and playstation in the living and also a 50" TV in the bedroom. Relax outside on a covered porch and enjoy the occasional local live music. Located close to the Prestonsburg Passage Trail, Mountain Arts Center, Middle Creek National Battlefield, Pikeville Exp Center and a short drive to the Red River Gorge.

Guest favourite
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, 75 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.

Top guest favourite
The cottage is a single-story building with a white exterior and a black roof. A decorative star is featured above the front window. A gravel driveway leads to a garage on the left, while a small porch with steps extends towards a well-maintained lawn with potted plants.
Home in Whitesburg
4.97 out of 5 average rating, 607 reviews

Cowan Creek Cottage

Cowan Creek Cottage is close to the Cowan Community Center and only 5½ miles outside the city limits of Whitesburg. The cottage is located at the foothills of Pine Mountain. You’ll love the cottage and enjoy the feel of having your own little home in the mountains. Enjoy a clean and comfortable home away from home while visiting friends and family and enjoying our community. Cowan Creek Cottage is good for couples, solo adventurers, business travelers, and families.

Superhost
Home in Inez
5 out of 5 average rating, 3 reviews

The Mountain Magnolia *Hot tub on private deck*

Step into bold industrial‑modern style with warm, comfortable furnishings that make relaxing effortless. This cozy home is packed with amenities! Featuring a private back deck complete with a steaming hot tub, charcoal grill, and outdoor sectional couch and chairs, perfect for unwinding under the trees. Designed for style and comfort, it’s an ideal retreat for couples, families, friends, or anyone craving a mountain getaway in a peaceful setting.

Guest favourite
The spacious bedroom features two queen beds adorned with vibrant red bedding and decorative pillows. Soft neutral walls create a calming atmosphere, while framed artwork adds visual interest. A bedside lamp provides additional lighting, enhancing the inviting feel of the room.
Apartment in Pikeville
4.98 out of 5 average rating, 45 reviews

Convenient & Modern 2 Bed Apt Free Wi-Fi & Parking

**Ideal Retreat for Professionals: Cozy 2 Bed near Pikeville Medical Center & UPike** Welcome to our stylish and comfortable one-bedroom apartment, thoughtfully designed with traveling professionals in mind! Our newly furnished and recently remodeled space boasts two queen beds with memory foam mattresses, ensuring a restful night's sleep after a busy day at work.

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
4.91 out of 5 average rating, 34 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.

Popular amenities for Pikeville vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Pikeville

Guest favourite
A comfortable gray sofa is positioned against a white shiplap wall, adorned with decorative wooden signs reading 'Pikeville' and 'Kentucky'. Two accent pillows with bold lettering are placed on the sofa, complemented by a small potted plant on a side table.
Apartment in Pikeville
4.95 out of 5 average rating, 228 reviews

The Cub House

Private room in Pikeville
4.67 out of 5 average rating, 6 reviews

Wooded Monastery Guest Suite

Superhost
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
4.99 out of 5 average rating, 111 reviews

The Red Dog Cottage In The Woods w/ Hot Tub

Guest favourite
The exterior of a two-bedroom apartment is shown with a textured driveway leading to the entrance. A climbing tree and landscaped flowerbed add greenery to the setting, while the building's light-colored siding contrasts with the surrounding natural environment.
Apartment in Pikeville
5 out of 5 average rating, 9 reviews

2 Bedroom Mountain Retreat

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
4.8 out of 5 average rating, 153 reviews

Living The Dream

Guest favourite
A modern living area features a soft gray sofa with a black accent pillow beside a small table. The kitchen is visible in the background, equipped with a white refrigerator and ample counter space. Recessed lighting and neutral walls create a bright and airy ambiance.
Home in Prestonsburg
5 out of 5 average rating, 26 reviews

Near Scenic Parks: Convenient Home in Prestonsburg

Guest favourite
A spacious living area features a plaid sectional sofa adorned with red accent pillows. A rustic wooden coffee table is positioned in the center. Two lamps stand on either side, providing additional lighting, beside a doorway that leads to other areas of the apartment.
Apartment in Pikeville
4.91 out of 5 average rating, 238 reviews

Sweet Dreams

Guest favourite
A modern bathroom features a walk-in shower with a glass panel and a light-colored curtain. A stylish vanity with a large mirror is complemented by a white sink and dark cabinetry. Natural wood flooring adds warmth, while a round rug is placed in front of the sink.
Apartment in Pikeville
4.91 out of 5 average rating, 69 reviews

2 king beds/1 bathroom• Apt 6

When is the best time to visit Pikeville?

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Avg. price$114 CAD$133 CAD$136 CAD$147 CAD$147 CAD$147 CAD$147 CAD$149 CAD$152 CAD$137 CAD$137 CAD$149 CAD
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.

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 $41 CAD per night before taxes and fees

  • Verified guest reviews

    Over 2,300 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    30 of Pikeville vacation rentals include wifi 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!

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