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Middlesboro Kentucky Hotels, Motels & Lodging

Check out our list of Middlesboro, Kentucky hotels, motels and other travel lodging options below. Hotels are listed by their proximity to downtown Middlesboro. Click on any hotel from the list below to view information, details, and current rates, and to make reservations online.

 
Sleep Inn & Suites Middlesboro

Map Marker Sleep Inn & Suites Middlesboro

1260 N, 12th Street, Middlesboro, KY

Rooms begin at $79.95

1 mile from Middlesboro city center.
Holiday Inn Express MIDDLESBORO

Map Marker Holiday Inn Express MIDDLESBORO

1252 N. 12TH STREET, Middlesboro, KY

Rooms begin at $89.00

0 miles from Middlesboro city center.
Days Inn Middlesboro, KY

Map Marker Days Inn Middlesboro, KY

1623 Cumberland Ave, Middlesboro, KY

Rooms begin at $60.00

0 miles from Middlesboro city center.

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Trails Near Middlesboro

  • Tri-State Peak Trail Middlesboro, KY (Hiking)
    A short walk to the ridgetop spot where Kentucky, Tennessee, and Virginia meet plus stops at Cumberland Gap and two Civil War fort sites. The states of Kentucky, Virginia, and Tennessee meet just sout...
  • Pinnacle Overlook Trail Middlesboro, KY (Hiking)
    A walk along a beautiful mountain stream to an overlook above Cumberland Gap. Sugar Run is a small, picturesque stream running down the Kentucky side of Cumberland Mountain. In spring the hollow is fu...
  • Wilderness Road Campground Hutch, KY (Campgrounds)
    Cumberland Gap National Historic Park, situated where Kentucky, Tennessee, and Virginia meet, is one of the South’s hidden jewels. I’ve been coming here for many years, and I continue to learn and enj...
  • Gibson Gap Trail Middlesboro, KY (Hiking)
    Pleasant stream crossings and impressive ridgetop overlooks. This hike gives you a good feel for the terrain that confronted Boone and all who have followed him to this isolated region. It’s a climb b...
  • Chained Rock Trail Pineville, KY (Hiking)
    A lovely wooded trail past a natural arch to an unusual lookout near the top of Pine Mountain. At the edge of a rock cliff face on Pine Mountain above the town of Pineville, a huge rock appears to per...
  • North Fork of the Cumberland River: Harlan to Lake Cumberland Harlan, KY (Whitewater Paddling)
    The North Fork of the Cumberland River (often referred to as simply the Cumberland) originates near Harlan at the confluence of the Poor Fork and Catron Creek and flows west draining the east Kentucky...
  • Pineville to Harlan: Where Coal was King Pineville, KY (Scenic Drives)
    This is another mountain drive through 90 miles of beautiful wooded hollows and along ridges. There are a number of abandoned as well as operating coal mines to be seen along the way. At one point, th...

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