Intramolecular and intracluster vibrational energy redistribution (IVR) from OH stretching vibrations of phenol and phenol dimer have been investigated for the first time by picosecond time-resolved IR-UV pump-probe spectroscopy. The OH stretching level was pumped by a picosecond IR laser pulse and the decay of the pumped level as well as appearance of the energy redistributed vibrational levels was observed using resonance enhanced multiphoton ionization scheme with a picosecond UV laser. For bare phenol, IVR of the OH stretching level was found to occur with a lifetime of 14 ps. For the dimer, a remarkable site-dependence was observed for the IVR lifetime of the OH stretching level; IVR of the proton-donating site occurs less than 5 ps, while that of the proton accepting site occurs with 14 ps. comparable to that of bare phenol. In the case of a cluster, IVR was followed by vibrational predissociation, which occurs with lifetimes of several tens of picoseconds.