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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.

Nature's Zen
SUPERHOST
Tiny house · 2 guests · 1 bed · 1 bath

Nature's ZenNestled 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

Scenic 1 BR Cabin w/ Hiking to Hensley Settlement
SUPERHOST
Entire cottage · 4 guests · 2 beds · 1 bath

Scenic 1 BR Cabin w/ Hiking to Hensley SettlementThe Elk Creek Cottage borders the 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, fish for Brook-Trout, 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.

Rustic Log Cabin on Powell River & Adventures🚣🏽‍♀️🎣
SUPERHOST
Entire cabin · 8 guests · 3 beds · 2 baths

Rustic Log Cabin on Powell River & Adventures🚣🏽‍♀️🎣Discover a breathtaking mountain and river living experience. You’ll stay in a fully furnished log house with everything you need to make memories that will last forever! 🐟🚣🏽‍♀️🚴‍♀️🥾 We also offer kayaking, mountain biking, hiking, fishing and camping. Send me a message through this listing to schedule your experiences. You can also check out everything on Airbnb’s “experiences” page. Ask about January’s discounts

Vacation rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Middlesboro vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Middlesboro

SUPERHOST
  1. Entire cottage
  2. LaFollette
A Hard Day’s Night - Lakefront with private dock
SUPERHOST
  1. Entire house
  2. Speedwell
Guest house in the country with a beautiful view
  1. Entire cottage
  2. LaFollette
Cottage near Powell Valley Marina
SUPERHOST
  1. Entire apartment
  2. Sharps Chapel
Pirate Cove - Lakefront on Norris Lake w/ dock
SUPERHOST
  1. Entire house
  2. Speedwell
Lucy's Lake House - Lake front with private dock
  1. Entire condominium
  2. LaFollette
Lakeside Condo @ Deerfield w/covered slip!
SUPERHOST
  1. Houseboat
  2. LaFollette
Norris Lake Water Haven (+optional pontoon rental)
SUPERHOST
  1. Entire cabin
  2. Claiborne County
NORRIS LAKE MOUNTAIN TOP CABIN
SUPERHOST
  1. Entire guest suite
  2. Cumberland Gap
The Inn over Angelo's
SUPERHOST
  1. Entire house
  2. Tazewell
Home away from home
SUPERHOST
  1. Entire house
  2. Rutledge
Farm house at “Hickory Hills”
SUPERHOST
  1. Entire house
  2. Sharps Chapel
Norris Lakefront Lodge

Nearby destinations