Holiday rentals in Lee County

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Top-rated holiday rentals in Lee County

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

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Top guest favourite
A charming farmhouse features a brick exterior and a welcoming front porch adorned with planters. Lush green grass surrounds the pathway leading to the entrance. A tree-lined hill serves as a serene backdrop, creating a peaceful rural setting.
Farm stay in Pennington Gap
5 out of 5 average rating, 78 reviews

“The Home Place” 3 Bedroom 2 Bath - Farm House

The “Home Place” is idea for visiting family or the perfect weekend getaway! It has beautiful Mountain View’s, and is in a very peaceful setting! Nestled in the mountains, but minutes from groceries, fast food & restaurants! Entertainment is also close by such as Lee Theatre & Axe Handle Distillery! Stone Mountain ATV Trails & Leeman Field RV Park are also close by! Hiking can be enjoyed at Natural Tunnel State Park, Cumberland Gap National Park, Sand Caves, Devil’s Bath Tub all within a hour!

Top guest favourite
A spacious, single-story home is reflected in the calm waters of a nearby pond, surrounded by greenery. A terrace features lounge chairs and an umbrella beside an in-ground swimming pool, with mountainous scenery in the background.
Home in Harlan
5 out of 5 average rating, 50 reviews

Harlan Hideaway - pool/hot tub/theater/game room

Enjoy your own little private resort in the heart of coal country! With 4 King beds and 4 Queen beds, everyone in your group will be sure to wake rested and ready for the day. With an in-ground swimming pool and water slide, basketball court, hot tub with outdoor tv, corn hole, and grill, the outdoor fun is endless. If it’s a little too cold or rainy, stay inside and enjoy the 6 recliners in the movie theatre room, shoot some pool, play air hockey, foosball, ping pong, or enjoy some board games.

Top guest favourite
A serene landscape showcases rolling hills dotted with grazing cows under a clear blue sky. Vibrant autumn trees in shades of orange and yellow frame the scene, while distant mountains are partially shrouded in mist, creating a peaceful rural setting.
Home in Dryden
4.99 out of 5 average rating, 109 reviews

Farm house with animals 10 minutes from Big Stone

Relax in our serene guest house situated atop a hill on a working farm on private country drive. Gorgeous 360 views of the surrounding mountains and pasture. Sip coffee on the front porch as the sun rises, and enjoy stunning sunsets from the back porch rockers! Cows, horses, sheep, donkey, deer closeby. Peaceful rural retreat with modern flare! Close to great dining and Trail of the Lonesome Pine outdoor drama in Big Stone Gap. Pickle balls and racquets provided for courts in Big Stone!

Top guest favourite
A mountain log cabin features a spacious wrap-around deck and large windows showcasing scenic views. Set against a lush green lawn, the cabin's wood exterior is complemented by natural stone accents. Surrounding trees add to the serene atmosphere.
Cabin in Jonesville
4.94 out of 5 average rating, 111 reviews

H&B Cabin and Farm at Wilder Bent

Beautiful mountain log cabin with modern amenities located on the Powell River. Our home has a spacious kitchen, large dinning table for family meals, and a gorgeous stone fireplace made from stone found on the property. The lower level is very private and is perfect for parents, in-laws, or teens. This is a peaceful get-a-way with plenty of fishing, hiking, and kayaking. Just a few minutes from Jonesville, VA, Hwy. 58 and tourist attractions in driving distance. Your home away from home!

Guest favourite
A comfortable living area is presented with two sofas positioned around a central coffee table. Natural light filters in through a door, while dark curtains provide a contrasting backdrop. Shelving displays decorative items, enhancing the space's functionality.
Home in Evarts
4.94 out of 5 average rating, 17 reviews

Welcome to The Mayor’s Retreat!

Relax with the whole family at this wonderful home! This is the former home of Mayor Burl Fee, who loved adventure tourism and welcoming visitors to our unique community. The home is located at the Bailey’s Creek entrance to Black Mountain Off-road Adventure Area, in the city limits of Evarts KY, the “Birthplace of Adventure Tourism”. You’re literally steps from the North Evarts RV Park. You can unload and ride directly to the ATV park or any of the local restaurants and convenience stores.

Top guest favourite
The front view of the ranch-style brick home reveals a neatly trimmed lawn and a metal roof. Windows frame the entrance, which features a decorative glass panel door. In the background, rolling hills display a serene rural landscape.
Farm stay in Jonesville
4.97 out of 5 average rating, 109 reviews

Maw's House Handicapped Friendly House in country

This two bedroom ranch style brick home located on a working farm will delight you with its view and open country spaces. Enjoy seeing wildlife such as deer, turkey, and squirrels on the property. This home is handicapped friendly. All entrances have a ramp, the bathroom commodes are raised, the shower in the main bath is handicapped, and there are grab bars in the necessary places. Equipment available for the handicapped are: Wheelchair, Lift Chair, Rollator, commode chair, walker.

Top guest favourite
Two spacious beds are arranged in a comfortable sleeping area, complemented by a fan overhead. Natural light filters through windows adorned with light curtains. A wooden bench and decorative wall mirrors add a cozy touch to the inviting space.
Guest house in Harlan County
5 out of 5 average rating, 26 reviews

Beautiful Loft in the Woods

Nestled in the scenic Appalachian Mountains, this spacious loft is perfect for outdoor lovers. With parking and sleeping for 4-6, it's an ideal base to explore nearby lakes, outlaw trails, or tow a few miles to Black Mountain Adventure Park. Enjoy amenities like an outdoor fire pit, waterfall, and a cozy living room with a large TV. Park your gear, relax by the firepit, and unwind in comfort. Whether for adventure or a peaceful retreat, this well-equipped loft is a perfect mountain retreat.

Top guest favourite
A charming white house is softly illuminated at night, showcasing its inviting exterior. Tall trees stand in the background against a deep blue sky, framing the peaceful rural setting.
Farm stay in Dryden
4.96 out of 5 average rating, 209 reviews

Wolfe-Gilbert House 1890 Victorian & farm

Great mountain views, ATV Trails, State and National parks, hiking, underground mine tour, all-in-a-day trips. You’ll love my place because of the comfy beds, the high ceilings, the views, wide open spaces, peace. My place is good for couples, big groups, and furry friends, let us know your needs. Located less than 5 miles to Spearhead Trail's Stone Mountain trailhead and only 30 minutes to Mountain View Trail. Two couples fit nicely in the 1st level 2 bedrooms for a quaint getaway.

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, 208 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, 350 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.

Top guest favourite
Home in Big Stone Gap
5 out of 5 average rating, 38 reviews

Gap House on the Lonesome Pine

Have fun with the whole family in my beautifully updated cottage nestled in the heart of the quaint mountain town of Big Stone Gap. Situated in an ideal location, and adjacent to The Trail of the Lonesome Pine outdoor drama. Within easy walking distance of great dining, coffee and ice cream shops, beautiful walking/hiking trails, the BSG visitor’s center, bike trails, parks, pickleball courts, fishing, kayaking, and more!

Guest favourite
A warm living area features rich cherry wood flooring and exposed brick walls. Comfortable seating is arranged around a well-lit space, with a stylish coffee table and decorative accessories present. A blend of antique and modern furnishings showcases the historic character of the property.
Guest suite in Cumberland Gap
4.91 out of 5 average rating, 215 reviews

The Inn over Angelo's

Detailed with antique mahogany trim, cherry wood flooring, hand-carved fireplace mantles and housed in a building built in 1890, this historic property has been many things over time. The Inn occupies 1,100 sf over Angelo's in the Gap, an Italian cuisine restaurant with recipes decades old. The Vault Tap House and Pub, showcasing 29 craft and domestic beers, features the original town bank vault, now a walk-in cooler.

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