A chromatic confocal point sensor (CPS) system and associated methods are provided for measuring holes. A CPS optical pen includes a beam dividing deflecting element that directs measurement light simultaneously along at least three directions to the interior surface of the hole. A CPS electronics portion comprises a light generator, a spectrometer, and a signal processor. In operation, the CPS pen directs measurement light to the interior surface along the at least three directions, and the spectrometer receives measurement light reflected from those directions back through the pen and provides a spectral intensity profile comprising spectral peak components corresponding to distances to the interior surface along those directions. The hole characteristic may be determined based at least partially on those distances. The CPS pen may be used as a probe on a coordinate measuring machine (CMM). The CPS pen does not require rotation in a hole to measure the hole.