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Vacation rentals in Middlesboro

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Top-rated vacation rentals in Middlesboro

Guests agree: these stays are highly rated for location, cleanliness, and more.

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
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
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

Stay near Middlesboro's top sights

Photo of Cumberland Gap National Historical Park Visitor Center
Cumberland Gap National Historical Park Visitor Center13 locals recommend
Photo of Shades Café & Steakhouse
Shades Café & Steakhouse10 locals recommend
Photo of Middlesboro Country Club
Middlesboro Country Club4 locals recommend

Other great vacation rentals in Middlesboro

Tiny home in Pineville
Nature's Zen
$75 per night
Cabin in Harrogate
Rustic Log Cabin on Powell River & Adventures🚣🏽‍♀️🎣
$135 per night
Serviced apartment in Harrogate
Harrogate Haven! LMU & Cumberland Gap (Pets OK!)
$99 per night
Home in Harrogate
Entire home. Spacious two bedroom.
$125 per night
Serviced apartment in Cumberland Gap
Beautiful 2BR Apartment w/ patio above restaurant
$116 per night
Home in Speedwell
Guest house in the country with a beautiful view
$99 per night
Guest suite in Cumberland Gap
The Inn over Angelo's
$150 per night
Serviced apartment in Harrogate
Bella Montagna - Near LMU & Pet Friendly!
$89 per night
Rental unit in Harrogate
Cozy two bedroom apt-nonsmoking
$97 per night
Cottage in Cumberland Gap
Cozy Cumberland Gap Cottage
$119 per night
Home in Harrogate
Blissful Bungalow across from LMU campus
$164 per night
Home in Middlesboro
Charming Crater City Craftsman
$182 per night
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  2. United States
  3. Kentucky
  4. Bell County
  5. Middlesboro