Mass-resolved IR spectra of cyclohexanol-water clusters and cyclohexanol dimer in supersonic expansions are presented for the first time. A combination of ns and fs IR lasers made possible recording such spectra without inclusion of a chromophore or a messenger atom. Furthermore, employment of the recently developed IR(3) technique [I. León, R. Montero, F. Castaño, A. Longarte, and J. A. Fernández, J. Phys. Chem. A 116, 6798 (2012)] allowed us to discriminate between the contribution of different species to the IR spectrum. Comparison of the experimental spectra with the predictions at the M06-2X∕6-311++G(d,p) calculation level confirmed the assignment of the spectrum of cyclohexanol[middle dot](H2O)1 to a structure in which water is accepting a proton from cyclohexanol's OH group, and those of cyclohexanol[middle dot](H2O)2,3 to structures with cyclic hydrogen bond networks. A comparative analysis of the results obtained with those reported on other aromatic alcohols is also offered.