We present a theoretical study of electron transport through a molecule connected to two metallic nanocontacts. The system investigated is 1, 4 benzene-dithiolate, chemically bonded to two Au contacts. The surface chemistry is modeled by representing the tips of the Au contacts as two atomic clusters and treating the molecule-cluster complex as a single entity in an extended Hückel tight-binding scheme. We model the tips using several different cluster geometries. An ideal lead is attached to each cluster, and the lead-to-lead transmission is calculated. The role of the molecule-cluster interaction in transport is analyzed by using single-channel leads. We then extend the calculations to multichannel leads that are a more realistic model of the tip’s environment. Using the finite-voltage, finite-temperature Landauer formula, we calculate the differential conductance for the different systems studied. The similarities and differences between the predictions of the present class of models and recent experimental work are discussed.