
Holiday houses in Cumberland Gap
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Top-rated holiday rentals in Cumberland Gap
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"LadyA" frame! Kayak+Hike+River+Glamp adventure!
Whether you're looking for a peaceful retreat or an adventurous escape, "Lady A" is a unique opportunity to unwind and recharge in the great outdoors. Designed to provide a comfortable and cozy stay, while still allowing you to feel fully connected to the natural world around. With dense forest bordering a river, relaxation & adventure awaits at every turn. Many adventures onsite & nearby: Winery-13m Drive thru Safari Park-7m Whitewater Raft-28m Smoky Mtns-45m Dollywood-45m Zipline 25m +more.

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

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.

Appalachian Mountain Log Cabin (Private Retreat)
The Cabin at GoodSoil Farm is the perfect solo get-a-way from it all! This cozy hand built log cabin is just right for reading, reflecting, retreating, or just resting. The Cabin sits as the centerpiece of our working mini-farm and comes replete with rocking chairs on the porch, a gurgling creek nearby, a stunning mountain view, and room to explore. Read a book, strum your guitar, prop up your feet, put on some coffee & leave your cares behind for a few days at The Cabin on GoodSoil Farm.

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 and no longer used for fishing except when private events have booked the entire property.

The Ambleside Cottage
The Ambleside Cottage offers full privacy for a single or a couple looking for a serene getaway surrounded by the beauty of the Appalachian mountains. This magical cabin is conveniently located for travelers, yet Ambleside feel like a remote retreat nestled in the woods above Elk Fork Creek. The Cottage is an adorable tiny house, offering 500 square feet of living space with a kitchenette, a sitting area, and a bathroom with a shower. The queen-size bed is upstairs in the sleeping loft.

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!

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.

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.

A Stay On Brentwood
This location is in the heart of Morristown with a variety of restaurants and quick access to interstate 40 and interstate 81. With the Néw interstate access, the drive to pigeon Forge is about 45 but could be longer depending on traffic. Guest are encouraged to allow more time during peak season ( March- December ) This listing is NOT a good fit for small or toddler children because of the kitchenette and fireplace.

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!

Rio House Retreat
Need time away from it all to recharge or refocus with love ones. With no traffic, neighborhood noise or city lights find your inner peace with the sounds and views of nature. The Rio House's goal is for you to do as little as possible, celebrate a magic moment or find inspiration. Have your bait or foosball skills ready to go or TV binge list ready, the Rio House can be the perfect getaway. Book Now!
Popular amenities for Cumberland Gap holiday rentals
Other great holiday rentals in Cumberland Gap

Welcome to the Parsonage at The Olde Church

Hot Tub MountainTop/Retreat 5 mins. to Norris Lake

Norris Lake Modern Farmhouse Retreat

Harrogate, TN - 5 min. From LMU

Cabin #4 - Gina Falls

Fall Foliage @ The Haven Norris Lake! 5Acres, Dock

Harrogate Haven! LMU & Cumberland Gap (Pets OK!)

Mountain View Retreat - 1 1/2 mile from LMU
Quick stats about holiday rentals in Cumberland Gap

Nightly prices starting at
Cumberland Gap holiday rentals start at $168 AUD per night before taxes and fees

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Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Cumberland Gap rentals

4.9 Average rating
Cumberland Gap stays are highly rated by guests—averaging 4.9 out of 5!
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