We use deep HST/ACS F555W and F814W photometry of resolved stars in the M81 Group dwarf irregular galaxy Ho II to study the hypothesis that the holes identified in the neutral ISM (HI) are created by stellar feedback. From the deep photometry, we construct color-magnitude diagrams (CMDs) and measure the star formation histories (SFHs) for stars contained in HI holes from two independent holes catalogs, as well as select control fields, i.e., similar sized regions that span a range of HI column densities. Converting the recent SFHs into stellar feedback energies, we find that enough energy has been generated to have created all holes. However, the required energy is not always produced over a time scale that is less than the estimated kinematic age of the hole. The combination of the CMDs, recent SFHs, and locations of young stars shows that the stellar populations inside HI holes are not coherent, single-aged, stellar clusters, as previously suggested, but rather multi-age populations distributed across each hole. From a comparison of the modeled and observed integrated magnitudes, and the locations and energetics of stars inside of HI holes, we propose a potential new model: a viable mechanism for creating the observed HI holes in Ho II is stellar feedback from multiple generations of SF spread out over tens or hundreds of Myr, and thus, the concept of an age for an HI hole is intrinsically ambiguous. We further find that halpha and 24 micron emission, tracers of the most recent star formation, do not correlate well with the positions of the HI holes. However, UV emission, which traces star formation over roughly the last 100 Myr, shows a much better correlation with the locations of the HI holes.