Holiday rentals in Pennington Gap

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Top-rated holiday rentals in Pennington Gap

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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, 73 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 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, 435 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 favourite
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, 185 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

Top guest favourite
A cozy tiny house retreat features wooden siding with vibrant blue accents. Two large windows on either side of the entrance invite natural light. A set of five wooden steps leads to a welcoming front porch, which includes two wooden chairs, surrounded by lush greenery.
Tiny home in Pineville
4.98 out of 5 average rating, 324 reviews

Nature's Zen

Nestled in a simple back to nature setting in one of Kentucky's oldest settlements (Pineville, KY) is the Nature's Zen, a tiny house retreat. If you are looking to disconnect from the hustle and bustle of life's craziness, Nature's Zen is calling your name. A quaint, restorative retreat where you can pause, take a deep breath and find refreshment for your soul and balance your life. Nature's Zen is for anyone looking for the quiet and solitude outside city limits. On FB @ Nature’s Zen Retreat

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, 108 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 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, 105 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
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, 163 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 favourite
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, 184 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!

Top guest favourite
A secluded cabin is surrounded by lush trees, offering shaded outdoor seating and a picnic area. Sunlight filters through branches, casting a warm glow. A hammock is visible beside a fire pit, creating a peaceful setting for relaxation and connection with nature.
Chalet in Sneedville
4.94 out of 5 average rating, 195 reviews

Getaway to a very private beautiful Cabin.

Recharge/ bonding needed? This retreat is ±8.6 miles from Sneedville, nestled Newman's Ridge facing Powell mountain. You’ll love this cozy cabin because of the views, the location, the ambiance, the outdoors space, mostly because you have escaped the every day grinding. Come here and unplug & unwind. Go for a stroll, watch the cows graze, look up at the mountain, get refreshed and recharged. There is a fast fiber optic internet access. AND, the leaves in the fall = spectacular!

Top guest favourite
The exterior of the chalet showcases a charming two-story structure with a distinctive red door. The landscaped yard features various plants and shrubs, bordered by a wooden fence, with a gravel pathway leading to the entrance. Lush greenery surrounds the property, emphasizing its natural setting.
Chalet in Kingsport
4.97 out of 5 average rating, 574 reviews

The Bearfoot Chalet Kingsport, TN

Our Mountain Chalet is the Perfect GETAWAY. Best location to stay in our ENTIRE Area. We are in the city limits of Kingsport, 3 miles from downtown. A DOG MUST BE PRE-APPROVED and there will be an additional pet fee. I do not charge a cleaning fee as long as guest leave place clean as found. Charter cable TV and WIFI access provided. Also located on our 6-acre estate is another BNB rental the "BEARFOOT RETREAT", a 3BR house should a larger group want to stay close together.

Top guest favourite
A single-level cottage is surrounded by a spacious yard, featuring a covered porch and a blend of green and brown siding. Colorful trees stand nearby, showcasing autumn foliage against a clear blue sky.
Cottage in Church Hill
4.92 out of 5 average rating, 548 reviews

Woodland Cottage

2BR/1BA One level cottage located on 8.5 acres surrounded by trees. Wi-Fi Internet w/ streaming services, 65" Smart TV, Netflix, Hulu, books & board games are provided: Tea, coffee & coffee maker are supplied. There is no cleaning fee, so please be clean & tidy up after yourselves. Woodland Cottage is kept fresh & clean; accommodates up to 6 people comfortably. We welcome everyone from all walks of life. We are 8 minutes from I-26 & 15 minutes from I-81 (via the I-26).

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
4.98 out of 5 average rating, 570 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.

Popular amenities for Pennington Gap holiday rentals

  1. Airbnb
  2. United States
  3. Virginia
  4. Lee County
  5. Pennington Gap