Density functional theory (DFT) calculations of the structures, binding energies, vibrational frequencies and infrared intensities of methanol clusters containing two to five molecules have been carried out using the Becke3LYP functional. Thirteen representative H-bonded structures have been studied including cyclic, chain, branched-cyclic and branched-chain hydrogen bond structures. In the methanol trimer, tetramer, and pentamer, the cyclic structure is more stable by 3.5, 8.3, and 3.6 kcal/mol over the next most strongly bound minimum. In the tetramer and pentamer, the second-most stable minimum corresponds to a branched cycle. Chain structures are destabilized from the cyclic minimum by the loss of a hydrogen bond and from a smaller cooperative strengthening of the II-bonds that remain. In all branched structures studied, the formation of the branch II-bond strengthens the "branch-point" methanol's H-bond donation to its neighbor, but weakens its two acceptor H-bonds, leading to largely compensating effects on the total binding energy. The computed OH stretch vibrational frequency shifts (relative to the monomer at the same level of calculation) are used as points of comparison with recent experimental work on gas-phase (methanol)(m) and benzene-(methanol)(m) clusters and matrix-isolated (methanol)(m) clusters.