Vacation rentals in Middlesboro

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Top-rated vacation rentals in Middlesboro

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Tiny home in Bell County

Pondview Overlook, a delightful tiny log cabin

If you are looking to disconnect from the hustle and bustle of life's craziness and reconnect with nature or just looking to get out of the city into a country setting then this tiny log cabin is whispering in your ear...come, come, come relax, push the pause button, take a deep breath of fresh mountain air, sit in a porch swing with a hot cup of coffee or a cool beverage while enjoying the sights and sounds of nature. Listen to the whispers of tranquility that come through on the gentle breeze.

$80 per night

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Cottage in Bell County

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.

$100 per night

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Rental unit in Cumberland Gap

Luxury Brooklyn St APT | Heart of Cumberland Gap

Luxury apartment located on one of the main streets of the historic town of Cumberland Gap, TN! Enjoy a weekend getaway at the foothills of the Appalachian Mountains. The apartment is well equipped with a full kitchen, bathroom, one bedroom, dining area, living room, washer/dryer, and a front porch with breathtaking views. Take full advantage of this home away from home in an optimal location with all the necessary amenities.

$119 per night