Places to stay in Middlesboro, Kentucky

Middlesboro, also spelled Middlesborough, is a city in Bell County, Kentucky. It is the principal city of the Middlesborough, KY Micropolitan Statistical Area. Middlesboro is the largest city in Southeast Kentucky. Local dining options include Ike’s Artisan Pizza, Shades Cafe & Steak House, Conley’s Drive-in Restaurants, and Yamato Japanese Steakhouse.

If you are travelling in the area, Middlesboro is located close to Besson Railroad Station (historical), Pigeon Roost Branch, Bell County Volunteer Fire Department Clear Creek Station, North Tazewell Volunteer Fire Department and Lee Cemetery.

Available Middlesboro lodging

We currently have 11 accommodations in and around Middlesboro.

Middlesboro Hotels, Motels, Resorts, B&Bs and Extended Stay

Bed & Breakfasts

The Olde Mill Inn Bed And Breakfast

Approx 4 miles away in Cumberland Gap:

Come stay in our Romantic First Class Secluded Bed and Breakfast where you can get away from everything and just spend time together snuggled up in our wonderful beds in one of our soft robes or stroll our little town and grab a cup of coffee and .....

603 Pennlyn Avenue

Cumberland Gap, Tennessee

Hotels

Econo Lodge

When you’re looking for accommodations that are easy to find, our pet-friendly Econo Lodge® hotel in Middlesboro is everything you could want and more. Located within easy reach of the area’s most prominent historic attractions.

1623 Cumberland Avenue

Middlesboro, Kentucky

Bed & Breakfasts

Cumberland Manor Bed & Breakfast

Step back in time and visit The Cumberland Manor, a grand Victorian built in 1890. This 6000 square foot home has inviting public rooms elegantly decorated with period antiques and a beautifully hand-carved staircase.

208 Arthur Hts.

Middlesboro, Kentucky

Bed & Breakfasts

The Olde Mill Inn Bed & Breakfast

Approx 4 miles away in Cumberland Gap:

Built in two phases, The Olde Mill Inn Bed & Breakfast is rich with historic detail and balanced with the modern amenities you seek. Seven guest rooms, all with private bathrooms, are decorated in the style of era in which the structure was built.

603 Pennlyn Avenue

Cumberland Gap, Tennessee

Hotels

Sleep Inn

Newly constructed in 2010 with amenities and location perfect for business or lesiure travelers. Shopping and restaurants nearby. Free hot breakfast daily.

1260 N, 12th Street

Middlesboro, Kentucky

Motels

Boone Trail Inn

Boone Trail Inn is located off the scenic Cumberlang Gap Parkway (U.S. 25E) near Middlesboro, Kentucky. The area is surrounded by beautiful mountains and blue skies. The inn is just south of Pine Mountain State Park and north of Cumberland Gap National Historic Park..

2105 US 25 East

Middlesboro, Kentucky

Hotels