Holiday rentals in Pineville

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Top-rated holiday rentals in Pineville

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

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Top guest favourite
A serene pond reflects the clear blue sky and surrounding greenery. Rolling hills and a field are visible in the background, creating a peaceful rural landscape. Trees line the edge of the pond, enhancing the natural setting.
Cabin in Jacksboro
5 out of 5 average rating, 101 reviews

Bolton Farm CJ’S Dream House 2bed/1bath

Relax with the whole family at this peaceful place to stay. Farm experience/relax and enjoy our 15 acre little piece of heaven.Sit on the deck overlook the fish pond,watch the mini animals play in the field. View goats, mini ponies/donkeys. free gated secure parking for your atv/boat trailer. Full stocked kitchen,tile walk in shower, washer/dryer, Qn bed, plus a queen sleeper sofa, 65” tv and gas grill on deck. 5 acre field is open to explore around pond. We love hosting travel or remote workers

Top guest favourite
The exterior of a rural home is displayed, featuring a welcoming front porch with wooden railings and seating. Lush greenery from the surrounding trees provides a natural backdrop. A dark blue front door and decorative elements, such as potted plants, enhance the inviting appearance.
Home in Big Creek
4.97 out of 5 average rating, 123 reviews

Daniel Boone Forest-Easy Park-I75-Hal Rogers Pkwy

Nestled within the Daniel Boone National Forest, approximately 13 miles from the Clay County seat of Manchester, our newly built, veteran-owned, pet-friendly, rural getaway awaits you and your guests! With several amenities including a private hot tub, twin-size porch bed swing, Nintendo Switch Game System, and fire pit with seating, you’re sure to feel right at home. Enjoy the thousands of acres of nearby hunting land, ATV trails (famous Red Bird Crest Trail, 0.9 miles away) or just relaxing!

Guest favourite
An aerial view captures the expansive green landscape of a golf course, bordered by trees and water features. The sun casts a soft glow over the rolling hills, highlighting the manicured fairways and bunkers below.
Home in Pineville
4.98 out of 5 average rating, 96 reviews

Pine Mountain Villa on Wasiota Winds Golf Course

Relax with the whole family at this peaceful place to stay. Awesome views every where you look in this 3 bedroom/2 bath home sitting directly on the 10th green. Large rock fireplace sits in the center of the home, perfect for family gatherings. Large Den perfect for entertaining and has a antique poker table that is perfect for any card games you wish to play. There is a screened in back porch complete with porch swing. Sitting area in front with 2 Adirondack chairs to enjoy the mountain views.

Top guest favourite
An inviting wooden porch is featured, adorned with potted plants and hanging ferns. Two chairs are positioned comfortably, offering a serene setting surrounded by greenery. Sunlight casts soft shadows on the porch floor, enhancing the tranquil ambiance of the space.
Cabin in Pineville
4.97 out of 5 average rating, 183 reviews

Outdoor Lover's Creekside Cabin (dog friendly)

Enjoy all the scenery of Bell county in this creekside cabin. Whether you prefer to hike, fish, ride sxs, or just enjoy scenery, we have it all. 3 min from Pine Mtn State Park and Wasioto Winds Golf Course, 7 min to downtown Pineville, 20 min to Cumberland Gap National Park. Kingdom Come State Park and Cumberland Falls are an hour drive. Load up your sxs or atv and ride one of the many trails right from the driveway! Black Mountain Off Road Park and Tackett Creek are also about an hour away.

Top guest favourite
A tiny home features a bright orange facade with a welcoming porch. A white door is flanked by a window, and steps lead up to the entrance. Surrounding grassy spaces are dotted with trees, and a fire pit is visible nearby.
Tiny home in Gray
4.96 out of 5 average rating, 286 reviews

Sleeping Turtle Tiny Home

We provide an escape that is situated near a spring lake with beautiful mountain views. It is located just over 11 miles off of the I75 exit. During the day you can find yourself searching out some local activities such as Cumberland Falls, Colonel Sanders Museum... When you're ready to relax; just sit back, make a campfire to roast marshmallows or fire up the barbecue grill! This is a FORMER paylake. Please don't expect to fish, as the paylake is closed.

Top guest favourite
An aerial view captures the unique repurposed silo with a circular design and a red tin roof. Surrounding greenery enhances the setting, while a hot tub and patio area with dining furniture are visible. Neatly arranged landscaping features small trees and decorative stones.
Farm stay in Sneedville
4.98 out of 5 average rating, 213 reviews

Red Bin

This memorable place is anything but ordinary. This repurposed Silo is located on a working farm. Featuring stunning craftsmanship and lots of relaxing amenities for up to two guest. The property includes stunning mountain views, hiking trails, a small creek for fishing, a luxurious spa, fire pit, and patio. AND, if you love the fall, the leaves can be spectacular here! The best is you do not have to fight the crowds in Smoky Mountain tourist traps!

Top guest favourite
The exterior of Elk Creek Cottage is showcased, featuring a wooden facade surrounded by trees in autumn hues. A gravel driveway leads to the steps, and a spacious porch is visible with seating areas under an overhang, inviting guests to enjoy the natural surroundings.
Cottage in Bell County
4.99 out of 5 average rating, 353 reviews

Scenic 1 BR Cabin w/ Hiking to Hensley Settlement

“Elk Creek Cottage” borders Cumberland Gap National Historical Park property--the pathway to the west, trailblazed by Daniel Boone himself! Stay and hike to Hensley Settlement or Shillalah Creek Falls, or relax with a cup of coffee on the porch surrounded by nature. Only a scenic twenty-minute drive to Middlesboro or Pineville, KY separates you from the "city." Come enjoy the peace and quiet that Elk Creek Cottage has to offer.

Guest favourite
Guest house in Middlesboro
4.96 out of 5 average rating, 120 reviews

Pumpkin Patch

The Pumpkin Patch is a warm and cozy 2 bedroom, 1 bath bungalow with an open concept. Situated in Middlesboro, KY the only city in the USA built inside a crater. This newly renovated home is located in a quiet neighborhood at the edge of town. You'll enjoy exploring Cumberland Gap National Park, LMU, Abraham Lincoln Museum and Library and the Old Town Ghost Tours. Small pets are allowed so bring your fur baby!

Top guest favourite
Home in Pineville
5 out of 5 average rating, 17 reviews

Cozy Cottage

Close to down town Pineville, LMU campus, Pine Mountain State Park, Bell Theater, Cumberland Gap National Park. This centrally located cottage is just 5 minutes from downtown Pineville & Wasioto Winds Golf Course. 7 minute drive to Pine Mountain State Park, 15 min to Middlesboro, 20 min to Lincoln Memorial University, 13 min drive to Cumberland Gap National Park, 30 min to Harlan and 60 min to Lynch.

Guest favourite
Flat in Cumberland Gap
4.91 out of 5 average rating, 106 reviews

The Gap Getaway - Luxury Apt Near LMU & Nat’l Park

Luxury apartment located on a main street of the historic town of Cumberland Gap, TN! Enjoy a weekend getaway at the foothills of the Appalachian Mountains. The apartment is well equipped with a full kitchen, bathroom, one bedroom, dining area, living room, washer/dryer, and a front porch with breathtaking views. Take full advantage of this home away from home with all the necessary amenities.

Top guest favourite
Home in London
4.97 out of 5 average rating, 113 reviews

The Central Perk

Needing a clean comfortable place to stay a night to rest from a long drive or an extended stay to enjoy all that London ky has to offer, we’re 2 minutes off the exit and minutes from all your favorite restaurants and coffee shops and minutes away from Cumberland Falls, major lakes, Wildcat ATV park and more so come be our Guest! Plus next to Saint Joesph Hospital mins from both I75 exits

Guest favourite
The exterior of the cottage is illuminated by warm string lights, creating a welcoming ambiance. A spacious deck is adorned with wooden beams, providing a cozy area for relaxation. Lush greenery surrounds the property, enhancing the natural setting.
Home in Tazewell
4.91 out of 5 average rating, 107 reviews

Rio House Retreat

Escape to The Rio House and reconnect with what matters most. With no traffic, no neighborhood noise, and no city lights, you’ll enjoy peaceful views, fresh air, and the calming sounds of nature. Relax, recharge, and celebrate special moments. Play foosball, binge your favorite shows, or simply unwind. Your quiet getaway starts here. Book today.

Popular amenities for Pineville holiday rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. Bell County
  5. Pineville