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Save up to $986 | Book Flight + Hotel at the same time^
Save up to $986 | Book Flight + Hotel at the same time^
Save up to $986 | Book Flight + Hotel at the same time^
Save up to $986 | Book Flight + Hotel at the same time^
Save up to $986 | Book Flight + Hotel at the same time^
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Save up to $986 | Book Flight + Hotel at the same time^

Middlesboro Vacations

Middlesboro Vacations

Got your plane ticket in your hand and your bags zipped up and ready to go? Read on for a few basic Middlesboro tips before you jet off.

If you wander 25 miles (40 kilometers) east of Williamsburg, or 30 miles (48 kilometers) southeast of Corbin, you'll end up in Middlesboro.

Visitors to this area of Eastern Kentucky will be sharing space with roughly 11,000 residents.

Middlesboro Vacation Packages

Spend less when you book an airfare and accommodation package through Travelocity. With more than 400 airline partners and 665,000 lodging options, your Middlesboro getaway is just a click or two away.

Our Customer 1st Guarantee offers the security of 24/7 personal assistance on everything from airfares and accommodations to car rentals and activities. If you somehow spot a cheaper price elsewhere, we will return the difference^.

Don't you wish you had flexibility in your vacation itinerary? All of our package bundles can be revised with no hidden fees. And as long as you get in quick, most accommodations don't charge fees either^.

Hotels in Middlesboro

Middlesboro isn't known for its huge assortment of accommodations. All the same, with 3 properties on offer via Travelocity, you should be able to find someplace cozy pretty easily. Book your room now so you don't miss out!

After a day of wandering the streets of Middlesboro, there's nothing more satisfying than returning to a comfortable room and an inviting bed. The Olde Mill Inn Bed & Breakfast and Sleep Inn & Suites are some of Travelocity's leading accommodations.

Where do you fly into for Middlesboro?

While you're planning your upcoming Middlesboro vacation, bear in mind that the nearest terminal, McGhee Tyson Airport (TYS), is approximately 60 miles (97 kilometers) to the south of the city center. Book your airfares, fill up your luggage and prepare for some exciting new adventures!

Can I rent a car in Middlesboro?

Forget about waiting around for the bus. Check out your car rental options via Travelocity and get the most out of your time in Middlesboro.

To be found 2 miles (3 kilometers) from the city's heart at 300 N 12th Street is Enterprise. Make your way over and you'll be cruising around in no time!

Places to Visit Near Middlesboro

If you've seen the very best of Middlesboro already, don't pack up and go just yet. You've actually got renowned attractions close at hand! Dollywood draws people from all continents of the globe. Sevierville, only 55 miles (89 kilometers) from Middlesboro, is a convenient base when visiting this unforgettable attraction.

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Top Middlesboro Hotels Deals

Sleep Inn & Suites $94
Sleep Inn & Suites

Sleep Inn & Suites

1260 N, 12th Street, Middlesboro, KY
     
    5.0
    of 5, from 1 reviews
    2.5 out of 5.0 Stars

    This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the fitness center and conveniences like a 24-hour front desk and laundry facilities.

    Holiday Inn Express Williamsburg $98
    Holiday Inn Express Williamsburg

    Holiday Inn Express Williamsburg

    56 West Highway 92, Williamsburg, KY
       
      4.0
      of 5, from 1 reviews
      2.5 out of 5.0 Stars

      This hotel features an indoor pool and a fitness center. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A business center, express check-out, and luggage storage are also on offer.

      Pine Mountain State Resort Park $88
      Pine Mountain State Resort Park

      Pine Mountain State Resort Park

      1050 State Park Road, Pineville, KY
         
        4.0
        of 5, from 6 reviews
        3.0 out of 5.0 Stars

        A golf course and a restaurant are featured at this hotel. Enjoy the outdoor pool and perks like free self parking and free WiFi. A picnic area, concierge services, and wedding services are also on offer.

        Holiday Inn Express Middlesboro $111
        Holiday Inn Express Middlesboro

        Holiday Inn Express Middlesboro

        1252 N 12th St, Middlesboro, KY
           
          3.5
          of 5, from 2 reviews
          2.5 out of 5.0 Stars

          This hotel features an outdoor pool and a fitness center. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

          Super 8 by Wyndham Williamsburg $54
          Super 8 by Wyndham Williamsburg

          Super 8 by Wyndham Williamsburg

          30 W Highway 92, Williamsburg, KY
             
            3.4
            of 5, from 9 reviews
            2.5 out of 5.0 Stars

            This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's an outdoor pool on site, and a 24-hour front desk and a picnic area are also provided.

            Cumberland Gap Inn $68
            Cumberland Gap Inn

            Cumberland Gap Inn

            630 Brooklyn Street, Cumberland Gap, TN
               
              3.0
              of 5, from 1 reviews
              2.5 out of 5.0 Stars

              This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a picnic area, and barbecue grills are also on offer.

              Days Inn by Wyndham Jellico - Tennessee State Line Get Rates
              Days Inn by Wyndham Jellico - Tennessee State Line

              Days Inn by Wyndham Jellico - Tennessee State Line

              1417 5th Street, Jellico, TN
                 
                2.9
                of 5, from 7 reviews
                2.0 out of 5.0 Stars

                This hotel features an outdoor pool and a spa tub. Traveling on business? Take advantage of the 2 conference rooms, along with free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

                Middlesboro Inn $96
                Middlesboro Inn

                Middlesboro Inn

                1623 Cumberland Avenue, Middlesboro, KY
                   
                  1.2
                  of 5, from 4 reviews
                  2.0 out of 5.0 Stars

                  A restaurant and a seasonal outdoor pool are featured at this motel.

                  Top Flight Deals

                  Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

                  ^Savings based on all package bookings made with Flight + Hotel on Travelocity.com from January 1, 2018 to December 31, 2018, as compared to the 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.

                  *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.