A measuring apparatus and a measuring method are provided, with which an accurate length measurement and position checking are achieved using a simple structure. The measuring apparatus according to the present invention is provided with a first and a second parallel prisms which capture light rays respectively reflected from a first and a second locations on one surface of an object to be measured, an optical lens which converges or diverges the light rays from the first and the second parallel prisms, an image sensor which captures the light rays from the optical lens, and converts images of the first and the second locations into an electrical signal, and a display unit which displays on one screen the images of the first and the second locations based on the electrical signal. According to the present invention, using just one optical system, measurement can be performed on one screen, as to multiple locations being spaced apart. Furthermore, an optical path can be refracted by 90 degrees with respect to the height direction just above the object to be measured, by means of the parallel prism. Therefore, size and height (work distance) of the optical system can be reduced, thereby downsizing the measuring apparatus.