Vacation rentals in Pennington Gap

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Top-rated vacation rentals in Pennington Gap

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Top guest favorite

A cozy log cabin is framed by lush greenery, featuring a welcoming covered porch with rocking chairs. The front stairway leads to the entrance, and carefully arranged flower beds add color to the landscape. An American flag is displayed, reflecting a sense of rustic charm.

Cabin in Rogersville

4.98 out of 5 average rating, 419 reviews

Cozy Country Log Cabin! NO cleaning or pet FEES!

Cozy log cabin on quiet 22+ wooded acres with creek and well stocked pond! Enjoy all the comforts of home in a rural, peaceful setting. Seasonal Babbling brook, covered porch, fire pit , picnic & BBQ pavilion, and hiking trails! Bring your hiking Boots ! Located just 11 miles from Rogersville (the second oldest city in Tennessee, founded by Davie Crocket's maternal grandparents!). Located 12 miles from Crockett Springs Park and Historic Site. Public boat launch located at Clinch River nearby.

Top guest favorite

A modern kitchen with light wood flooring and green walls is illuminated by recessed lighting. A wooden dining table is surrounded by six chairs, and a patterned rug rests beneath it. The kitchen cabinetry is stylish, with appliances and open shelving visible in the background.

Home in Kingsport

5 out of 5 average rating, 159 reviews

Little Red House on the corner

This stylish place to stay has recently been fully renovated, fully furnished with all the necessities, 2 Bedroom, 2 full baths. The Couch can be converted into an additional bed, allowing for for 6 guests. Open and inviting space w/ 10' Ceilings . There are smart TVs in both bedrooms, living and dining room. Kitchen has Induction Stove, dishwasher, microwave, plates, glasses, silverware, pots, pans and much more. Complimentary Coffee, bathroom supplies - toothpaste, toothbrush ,soap and shampoo

Guest favorite

A rustic cabin stands surrounded by lush greenery, featuring a wooden exterior and a sloping roof. A stone pathway leads to the front porch, which includes steps for easy access. A balcony overlooks the serene landscape, enhancing the cabin's charm.

Cabin in Sneedville

4.9 out of 5 average rating, 118 reviews

Rustic Retreat Cabin - Peace andTranquility

If you are looking for a peaceful place to relax and recharge then look no further. Rustic Retreat is a beautiful little cabin located in the majestic hills of Hancock Co. TN. This newly remodeled retreat is located about 2 1/2 miles from the town of Sneedville on Prospect Ridge. It provides all the basic amenities to make your stay as comfortable as possible. You can sit on the porch and enjoy the view, go for a walk or just relax inside, reading or watching TV. Join us, unplug and relax.

Guest favorite

A wooden pathway leads to a raised deck, illuminated by warm string lights among the trees. An outdoor screen is positioned above, creating a cozy movie-watching space surrounded by nature, while the darkness of night accentuates the inviting ambiance.

Camper/RV in Jonesville

4.87 out of 5 average rating, 166 reviews

Happy Camper w/ Theater ·Hot-Tub ·Fire Pit

This is not just an accomodation, it is an experience accommodation! Enjoy camping in our luxury mountain escape! You can reconnect with nature while luxury furnishings and full amenities provide all the comforts of home inside a luxury camper. Add in an epic outdoor entertaining area featuring a theater with 120” screen, hot tub, griddle, outdoor grill, firepit, and deck and you have the ultimate camping adventure. Bonus – the property is on 25 acres in the VA mountains w/ views of KY and TN!

Guest favorite

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

4.93 out of 5 average rating, 105 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!

Top guest favorite

A modern tiny home is nestled among greenery, featuring a spacious porch supported by sleek black pillars. The exterior showcases a combination of wood and stone accents, while outdoor seating with a small table invites relaxation. Large windows provide ample natural light.

Tiny home in Surgoinsville

4.96 out of 5 average rating, 149 reviews

Eloheh

Amazing tiny home situated on 23 very private acres, conveniently located just off main highway. Newly constructed in 2023, this modern studio offers an enormous amount of amenities including full kitchen, dual showers, hot tub, outdoor TV, high speed WiFi, multiple TV viewing services, outdoor dining set, grill, multiple fire features, mountain views, lots of room for short hikes or nature walks, area with sunset views only a short distance from the house, only 1.5 miles to riverfront park.

Top guest favorite

A welcoming entrance to the Mountain Escape Cottage is depicted, featuring a wooden sign displaying the name prominently. Colorful flower pots filled with vibrant blooms frame the entrance, while the cottage stands amidst a backdrop of trees under a clear blue sky.

Cottage in Lynch

4.98 out of 5 average rating, 172 reviews

Cozy 3-BR 2-bath cottage near highest point in KY

Nestled in the heart of Lynch, KY, surrounded by comforting mountains, sets the Mountain Escape Cottage. Less than 1 mile from Portal 31, you can dive deep into the rich history of this tiny coal town. Within minutes you can drive to ATV parks, the highest point in KY, and many other mountainous adventures. Grab some coffee at the old cafe turned coffee shop, and visit the KY Coal Museum just 5 minutes away in Benham, KY. You and your family will leave here with beautiful mountain memories!

Guest favorite

An aerial view of a rustic log cabin framed by grassy terrain. The cabin features a metal roof and is surrounded by landscaped gardens. Outdoor seating is visible on the porch, enhancing the cabin's natural appeal against the backdrop of the Appalachian mountains.

Cabin in Whitesburg

4.98 out of 5 average rating, 187 reviews

BROWN’S ELK CABIN

Brown’s elk cabin is an Authentic, rustic, log cabin. Located in the heart of the beautiful Appalachian mountains, overlooking the KY river, Only a short drive to Pine Mtn hiking trails, Bad Branch Falls, Little Shepherd Trail, Kingdom Come State Park, Raven Rock golf course, and only twenty minutes from the Va. state line. Perfect getaway for relaxing with family and friends, sitting by the fire pit, or exploring the areas natural beauty. Located 3 miles from Whitesburg

Top guest favorite

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

4.98 out of 5 average rating, 550 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.

Top guest favorite

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, 188 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 ammenities for up to two guest. The property includes stunning mountain views, hiking trails, a creek for fishing, a hot tub, and 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 favorite

A lush green landscape is visible, featuring gentle hills under a clear blue sky. A wooden gazebo sits in the distance, surrounded by trees. The area is well-kept, with various shades of grass and greenery creating a serene outdoor environment.

Cabin in Sneedville

4.92 out of 5 average rating, 131 reviews

Lee's Sweet Retreat

An off the grid getaway between Rogersville & SneedvilleTN. on Clinch Mt. at the historic Martin's Gap. Lee's Sweet Retreat includes 4 cabins & 1 "hippie school bus", a fully furnished outdoor kitchen, bath house, outhouse, pavilion/stage/eating area. Great venue for getting back to Nature...or testing yourself off the grid. Spark your 5 Senses with the Scenic Beauty and Touch of Whimsy that is Lee's Sweet Retreat. Open May to October.

Top guest favorite

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

4.98 out of 5 average rating, 333 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.