This work is focused on the thermodynamic optimization of Organic Rankine Cycles (ORCs), coupled with absorption or adsorption cooling units, for combined cooling heating and power (CCHP) generation from biomass combustion. Results were obtained by modelling with the main aim of providing optimization guidelines for the operating conditions of these types of systems, specifically the subcritical or transcritical ORC, when integrated in a CCHP system to supply typical heating and cooling demands in the tertiary sector. The thermodynamic approach was complemented, to avoid its possible limitations, by the technological constraints of the expander, the heat exchangers and the pump of the ORC. The working fluids considered are: n-pentane, n-heptane, octamethyltrisiloxane, toluene and dodecamethylcyclohexasiloxane. In addition, the energy and environmental performance of the different optimal CCHP plants was investigated. The optimal plant from the energy and environmental point of view is the one integrated by a toluene recuperative ORC, although it is limited to a development with a turbine type expander. Also, the trigeneration plant could be developed in an energy and environmental efficient way with an n-pentane recuperative ORC and a volumetric type expander.