A drilling device for forming an enlarged-diameter hole includes: a guide sleeve with a cylindrical body and a guide to be inserted into a bottomed hole; a slide body that slides in the cylindrical body; and a bit holder provided on the slide body swingably; and a diameter-enlarging bit with a cutting blade. The bit slides between a first position where the cutting blade is separated from a bottom of the bottomed hole and a second position where the cutting blade is closer to the bottom than that at the first position. The guide has: a guide piece that guides the cutting blade to a side part, of the bottomed hole, following an advance of the bit from the first position to the second position; and an opening which allows passage of the bit removed from the bit holder where the bit is at the first position.