Earth-sized exoplanets that transit nearby, late spectral type red dwarfs will be prime targets for atmospheric characterization in the coming decade. Such systems, however, are difficult to find via wide-field transit surveys like Kepler or TESS. Consequently, the presence of such transiting planets is unexplored and the occurrence rates of short-period Earth-sized planets around late M dwarfs remain poorly constrained. Here, we present the deepest photometric monitoring campaign of 22 nearby late M dwarf stars, using data from over 500 nights on seven 1-2 meter class telescopes. Our survey includes all known single quiescent northern late M dwarfs within 15 pc. We use transit-injection-and-recovery tests to quantify the completeness of our survey, successfully identify most ($>80\%$) transiting short-period (0.5-1 d) super-Earths ($R > 1.9 R_⊕$), and are sensitive ($∼50\%$) to transiting Earth-sized planets ($1.0-1.2 R_⊕$). Our high sensitivity to transits with a near-zero false positive rate demonstrates an efficient survey strategy. Our survey does not yield a transiting planet detection, yet it provides the most sensitive upper limits on transiting planets orbiting our target stars. Finally, we explore multiple hypotheses about the occurrence rates of short-period planets (from Earth-sized planets to giant planets) around late M dwarfs. We show, for example, that giant planets at short periods ($<1$ day) are uncommon around our target stars. Our dataset provides some insight into occurrence rates of short-period planets around TRAPPIST-1-like stars, and our results can help test planetary formation and system evolution models, as well as guide future observations of nearby late M dwarfs.