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Middlesboro Vacations

Pack those stellar shades. We have Middlesboro vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Middlesboro – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Middlesboro vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Middlesboro

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Middlesboro vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Middlesboro well.

Top Hotel Deals

See all 60 Hotels in Middlesboro
Sleep Inn & Suites

Sleep Inn & Suites

1260 N, 12th Street, Middlesboro
    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 ...

    Sleep Inn & Suites$115

    Sleep Inn & Suites$115
    Holiday Inn Express Middlesboro

    Holiday Inn Express Middlesboro

    1252 N 12th St, Middlesboro
      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 ...

      Holiday Inn Express Middlesboro$111

      Holiday Inn Express Middlesboro$111
      Middlesboro Inn

      Middlesboro Inn

      1623 Cumberland Avenue, Middlesboro
        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 ...

        Middlesboro Inn$102

        Middlesboro Inn$102
        Pine Mountain State Resort Park

        Pine Mountain State Resort Park

        1050 State Park Road, Pineville
          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 ...

          Cumberland Inn & Museum

          Cumberland Inn & Museum

          649 S 10th St, Williamsburg
            3.5 out of 5.0
             
             

            Situated in Williamsburg, this hotel is 1 mi (1.6 km) from Kentucky Splash Water Park and within 16 mi (25 km) of Memorial Park and The Arena at SE KY Agricultural ...

            Cumberland Inn & Museum$99

            Cumberland Inn & Museum$99
            Super 8 by Wyndham Williamsburg

            Super 8 by Wyndham Williamsburg

            30 W Highway 92, Williamsburg
              2.5 out of 5.0
               
               

              Situated in Williamsburg, this hotel is 1 mi (1.6 km) from Kentucky Splash Water Park and 11.7 mi (18.9 km) from Memorial Park. The Arena at SE KY Agricultural ...

              Super 8 by Wyndham Williamsburg$59

              Super 8 by Wyndham Williamsburg$59
              Days Inn by Wyndham Jellico - Tennessee State Line

              Days Inn by Wyndham Jellico - Tennessee State Line

              1417 5th Street, Jellico
                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 ...

                Days Inn by Wyndham Jellico - Tennessee State Line$77

                Days Inn by Wyndham Jellico - Tennessee State Line$77
                Quality Inn

                Quality Inn

                2608 South Highway 421, Harlan
                  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. ...

                  Best Western Wilderness Trail Inn

                  Best Western Wilderness Trail Inn

                  1476 S US Highway 25E, Barbourville
                    2.5 out of 5.0
                     
                     

                    Situated in Barbourville, this hotel is 2 mi (3.2 km) from Barbourville Water Park and 6.6 mi (10.7 km) from Dr Thomas Walker State Park. Wasioto Winds Golf ...

                    Best Western Wilderness Trail Inn$100

                    Best Western Wilderness Trail Inn$100
                    Cumberland Gap Inn

                    Cumberland Gap Inn

                    630 Brooklyn Street, Cumberland Gap
                      2.5 out of 5.0
                       
                       

                      Situated in Cumberland Gap, this motel is 0.9 mi (1.4 km) from Cumberland Gap National Historical Park and within 6 mi (10 km) of Middlesboro Mall and Bell County ...

                      Top Flight Deals

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