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Middlesboro Vacation Packages

Welcome to Middlesboro! Although you won't be ticking off the world's greatest tourists attractions here, you'll still have an unforgettable time.

Save Time and Money with a Middlesboro Package Deal

It's time to save with your Expedia deal. Our flexible flight and lodging packages are the best way to save time and money. With the extra money, now you can do a little extra shopping in Middlesboro.

Savvy travelers can get savings up to $583 by booking their combined package deals with us.

Look around our international database of 400 airline partners and 321,000 hotels worldwide.

The super discounts at Expedia will make budgeting for your vacation that much more enjoyable. What are you waiting for?

If you have to change your vacation plans we will honor your cancellation request with no extra fee from us, on almost all reservations.

Middlesboro Vacation Packages

The notable city of Lexington is just 110 miles northwest of Middlesboro.

If it's a clear day, check out Smith Recreation Area Beach. It's only 25 miles to the east and is a fantastic place to absorb the ocean vistas.

Put on a comfortable pair of shoes and discover the magic at Big Ridge State Park, located 30 miles from Middlesboro. Another option is Cumberland Gap National Historical Park, which is 12 miles away.

You can learn about the fascinating culture of this area at Bell County Historical Society Museum.

Time to loosen the purse strings? Middlesboro Mall is the place for a spending spree.

Dr. Thomas Walker State Historic Site and Dr Thomas Walker State Park are just a handful of the worthwhile places in Bryants Store, a destination 13 miles away from Middlesboro. Lone Mountain Boat Dock and Straight Creek Boat Dock are more places. These are 18 miles out of Middlesboro, in New Tazewell.

Consider taking the family to Kodak, a regional hub just 45 miles to the south of Middlesboro. This area offers several visitor attractions, such as Adrenaline Park, Wild WaterDome and Eagle's Landing Golf Club. Wheatlands Plantation and Mountain Cove Marina are some more sites that ought to be on every traveler's schedule.

Adventurous travelers looking to get up and get active outdoors ought to try rock climbing and mountain climbing.

It's important to slow down the pace from time to time. You'll be glad to know that Eastern Kentucky is the perfect place to do just that. Feel all your stress melt away as you head out for a bit of shore fishing and camping.

If you happen to be a watersport buff, you should enjoy your time boating or fishing.

Your closest airport is McGhee Tyson Airport, and it is roughly 60 miles to the south.

Accommodation in Middlesboro

Securing the perfect place to stay is a vital part of any trip. Accommodation options in Middlesboro itself are a little limited, so check out Expedia's comprehensive Middlesboro lodging page straight away for the best deals.

Middlesboro lodgings include the Sleep Inn & Suites and Holiday Inn Express Middlesboro.

*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.


Top Hotel Deals

See all 42 Properties in Middlesboro
Sleep Inn & Suites $92
Sleep Inn & Suites

Sleep Inn & Suites

1260 N, 12th Street, Middlesboro
     
    4.7
    of 5, from 167 reviews
    2.5 out of 5.0

    Located in the heart of Middlesboro, this hotel is 0.3 mi (0.6 km) from Middlesboro Mall and 1.5 mi (2.5 km) from Bell County Historical Society Museum. Cumberland Gap National Historical Park and Wasioto Winds Golf Course are also within 9 mi (15 km).

    Holiday Inn Express Middlesboro $111
    Holiday Inn Express Middlesboro

    Holiday Inn Express Middlesboro

    1252 N 12th St, Middlesboro
       
      4.5
      of 5, from 217 reviews
      2.5 out of 5.0

      Situated in Middlesboro, this hotel is 0.2 mi (0.3 km) from Middlesboro Mall and 1.4 mi (2.3 km) from Bell County Historical Society Museum. Cumberland Gap National Historical Park and Wasioto Winds Golf Course are also within 9 mi (15 km).

      Middlesboro Inn $84
      Middlesboro Inn

      Middlesboro Inn

      1623 Cumberland Avenue, Middlesboro
         
        2.4
        of 5, from 143 reviews
        2.0 out of 5.0

        Situated in Middlesboro, this motel is within 1 mi (2 km) of Bell County Historical Society Museum and Middlesboro Mall. Cumberland Gap National Historical Park is 2.6 mi (4.3 km) away.

        Pine Mountain State Resort Park $95
        Pine Mountain State Resort Park

        Pine Mountain State Resort Park

        1050 State Park Road, Pineville
           
          4.4
          of 5, from 125 reviews
          2.5 out of 5.0

          Situated in Pineville, this golf hotel is 0.4 mi (0.6 km) from Pine Mountain State Resort Park and within 12 mi (20 km) of Wasioto Winds Golf Course and Middlesboro Mall. Bell County Historical Society Museum and Cumberland Gap National Historical Park are also within 20 mi (32 km).

          Cumberland Inn & Museum $93
          Cumberland Inn & Museum

          Cumberland Inn & Museum

          649 S 10th St, Williamsburg
             
            4.5
            of 5, from 377 reviews
            3.5 out of 5.0

            Situated in Williamsburg, this hotel is 1.3 mi (2.1 km) from Kentucky Splash Water Park and within 16 mi (25 km) of Memorial Park and The Arena at SE KY Agricultural and Expo Complex. Cumberland Falls and Dr Thomas Walker State Park are also within 25 mi (40 km).

            Super 8 by Wyndham Williamsburg $59
            Super 8 by Wyndham Williamsburg

            Super 8 by Wyndham Williamsburg

            30 W Highway 92, Williamsburg
               
              3.1
              of 5, from 169 reviews
              2.5 out of 5.0

              Situated in Williamsburg, this hotel is 1.3 mi (2.1 km) from Kentucky Splash Water Park and 11.7 mi (18.9 km) from Memorial Park. The Arena at SE KY Agricultural and Expo Complex and Cumberland Falls are also within 20 mi (32 km).

              Days Inn by Wyndham Jellico - Tennessee State Line $66
              Days Inn by Wyndham Jellico - Tennessee State Line

              Days Inn by Wyndham Jellico - Tennessee State Line

              1417 5th Street, Jellico
                 
                3.2
                of 5, from 111 reviews
                2.0 out of 5.0

                Situated in a state park, this hotel is 1.4 mi (2.2 km) from Memorial Park and within 25 mi (40 km) of Kentucky Splash Water Park and Campbell County Historical Society. La Follette Country Club and Cove Lake State Park are also within 32 mi (52 km).

                Quality Inn $87
                Quality Inn

                Quality Inn

                2608 South Highway 421, Harlan
                   
                  4.0
                  of 5, from 68 reviews
                  2.5 out of 5.0

                  Located in the heart of Harlan, this hotel is 0.8 mi (1.3 km) from Harlan Appalachian Regional Healthcare Hospital and 1.9 mi (3 km) from The Harlan Center. Black Mountain Offroad Adventure Area - Putney Trailhead is 11.3 mi (18.2 km) away.