We have obtained three epochs of Chandra ACIS-I observations (totaling ∼184 ks) of the nearby spiral galaxy NGC 300 to study the logN -logS distributions of its X-ray point source population down to ∼2×10 −15 erg s −1 cm −2 in the 0.35-8 keV band (equivalent to ∼10 36 erg s −1 ). The individual epoch logN -logS distributions are best described as the sum of a background AGN component, a simple power law, and a broken power law, with the shape of the logN -logS distributions sometimes varying between observations. The simple power law and AGN components produce a good fit for "persistent" sources (i.e., with fluxes that remain constant within a factor of ∼2). The differential power law index of ∼1.2 and high fluxes suggest that the persistent sources intrinsic to NGC 300 are dominated by Roche lobe overflowing low mass X-ray binaries. The variable X-ray sources are described by a broken power law, with a faint-end power law index of ∼1.7, a bright-end index of ∼2.8-4.9, and a break flux of ∼8×10 −15 erg s −1 cm −2 (∼4×10 36 erg s −1 ), suggesting they are mostly outbursting, wind-fed high mass X-ray binaries, although the logN -logS distribution of variable sources likely also contains low-mass X-ray binaries. We generate model logN -logS distributions for synthetic X-ray binaries and constrain the distribution of maximum X-ray fluxes attained during outburst. Our observations suggest that the majority of outbursting X-ray binaries occur at sub-Eddington luminosities, where mass transfer likely occurs through direct wind accretion at ∼1-3% of the Eddington rate.