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Holiday rentals in Middlesboro

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Middlesboro

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

Scenic 1 BR Cabin w/ Hiking to Hensley Settlement
SUPERHOST
Entire cottage · 4 guests · 2 beds · 1 bathroom
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.
Harrogate Home with Mountain Views
Entire residential home · 8 guests · 4 beds · 2 bathrooms
Harrogate Home with Mountain Views3 bedroom 2 bath pet friendly home. With wonderful views of the East TN mountains year round! Located 2 miles from Lincoln Memorial University. Less than 5 miles from the town of Cumberland Gap and Middlesboro, Ky. Close to Norris Lake. We take pride in ensuring cleanliness and follow strict COVID cleaning standards provided by the CDC.
Rustic Log Cabin on Powell River & Adventures🚣🏽‍♀️🎣
SUPERHOST
Entire cabin · 8 guests · 3 beds · 2 bathrooms
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 discounts.

Holiday rentals for every style

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Popular amenities for Middlesboro holiday rentals

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

Other great holiday rentals in Middlesboro

  1. Entire residential home
  2. Harrogate
3 bdrm ranch w/view of LMU & mountains!
₹6,375 per night
  1. Entire residential home
  2. Harrogate
Cabin on the Tolliver Manor property
₹8,073 per night
SUPERHOST
No reviews yet
  1. Entire serviced apartment
  2. Cumberland Gap
Studio in Historic Cumberland Gap
₹9,675 per night
  1. Entire residential home
  2. Harrogate
Moms House
₹5,882 per night
SUPERHOST
  1. Private room
  2. Harrogate
Liz's Extra College Room
₹1,436 per night
  1. Entire residential home
  2. Harrogate
Tolliver Manor
₹21,945 per night
  1. Private room
  2. Cumberland Gap
Cozy Cumberland Gap Cottage
₹9,043 per night
  1. Private room
  2. Harrogate
Queen Room 1 within the Tolliver Manor
₹6,000 per night
  1. Entire residential home
  2. Speedwell
Tackett House
₹7,553 per night
  1. Entire residential home
  2. Speedwell
Tackett House II
₹7,650 per night
No reviews yet
  1. Private room
  2. Ewing
Railsplitter Rentals LLC 2A - Perfect for LMU Clinical Students
₹1,800 per night
  1. Entire residential home
  2. Middlesboro
Crater City Cottage
₹13,425 per night