Botrytis cinerea isolates from flowers and berries of Vitis vinifera 'Thompson seedless' (grapevine) were characterized in terms of two transposable elements (TEs) Boty and Flipper, random amplified polymorphic DNA (RAPD), infection levels, and resistance to iprodione. The isolates were collected from grapevines under fungicide programs of variable numbers of iprodione applications, and replicated in three Chilean Central Valley locations. Recovery was repeated from clusters collected at four phenological stages. Highest infection levels were found at bloom. Fungicide programs including one iprodione application or a combination of other fungicides were most effective for reducing gray mold symptoms. A total of 457 isolates collected from fungicide programs including only one iprodione application, and the control program, were tested for the presence of TEs. In all locations and during all phenological stages, transposa isolates (containing both TEs) were most common, followed by Boty. Vacuma isolates (containing neither TE) were identified at very low levels in two locations and only in the control treatment, and isolates with only Flipper were not detected at any time or location. Vacuma and Boty isolates were all sensitive to iprodione, while transposa isolates showed a wide range of resistance. Based on response to iprodione, the presence of TEs, and presence of vegetative-incompatibility alleles (Bc-hch), the isolates studied belong to B. cinerea Group II, a phylogenetic species within B. cinerea. Hierarchical analysis of molecular variance and genetic diversity analyses of the RAPD genotypes showed a genetic differentiation linked to location, but it was not related to geographic distance. Moreover, a genetic differentiation related to the phenological stage of grapes was also detected.