
Holiday rentals in Pennington Gap
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Top-rated holiday rentals in Pennington Gap
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Mamaws House-Natural Tunnel, Devils Bathtub Hwy 23
Nostalgia and comfort at Mamaw’s House. We are honoring our Mamaws, Grandmother, Granny and mothers; sharing their talents, interests, and love with you. Everyone belongs at Mamaw's House. The family areas are for fun, games and conversation. The sitting room, breakfast area, porch, and “mud” room give you a place to create or relax. Keeping with modern times, each of the bedrooms have workspaces, comfy beds, full size mirrors, YouTube tv and high speed WiFi . So come on in and stay awhile.

“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!

Deer Meadow-Devil's Bathtub/Natural Tunnel
Escape to Deer Meadow, a charming cabin offered by Appalachian Mountain Cabins, nestled in the heart of the mountains. This dog friendly inviting retreat features a master bedroom with a luxurious whirlpool tub—perfect for romantic evenings. Upstairs, you’ll find a cozy loft with two full-size beds, ideal for couples, kids, or extra guests. Named for the peaceful meadow just outside, where deer often graze in the early morning and evening, creating a serene and memorable setting for your stay.

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!

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!

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.

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.

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!

Clinch River farm stay -stunning mountain views
Cozy new cabin on a 200-acre historic farm on the Clinch River. Enjoy easy river and creek access on the property, beautiful mountain views, a fire pit, outdoor dining, porch swings, and hammocks. Hike quiet farm roads, watch wildlife, splash in the creek, or fish and float the river. Play outdoor games - badminton, horseshoes, and croquet. Perfect for couples or families, with a queen bed, 2 twins and a sleeper sofa, full kitchen, and covered porches for dining, reading, or relaxing.

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.

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!

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.
Popular amenities for Pennington Gap holiday rentals
Other great holiday rentals in Pennington Gap

Dan’s Den - Two bedroom home with outdoor firepit

Bear Creek Cabin • Vineyard Views & Fishing Pond

Daffodil Dream Camper W/Theater ·Hot-Tub ·Fire Pit

Mamaw Jewell’s Cabin

Welcome to The Mayor’s Retreat!

Gap House on the Lonesome Pine

Serenity on the Clinch River

Joe’s place (trailer parking available )
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