The energy transition towards a scenario with 100% renewable energy sources (RES) for the energy system is starting to unfold its effects and is increasingly accepted. In such a scenario, a predominant role will be played by large photovoltaic and wind power plants. At the same time, the electrification of energy consumption is expected to develop further, with the ever-increasing diffusion of electric transport, heat pumps, and power-to-gas technologies. The not completely predictable nature of the RES is their well-known drawback, and it will require the use of energy storage technologies, in particular large-scale power-to-chemical conversion and chemical-to-power re-conversion, in view of the energy transition. Nonetheless, there is a lack in the literature regarding an analysis of the potential role of small–medium CCHP technologies in such a scenario. Therefore, the aim of this paper is to address what could be the role of the Combined Heat and Power (CHP) and/or Combined Cooling Heat and Power (CCHP) technologies fed by waste heat within the mentioned scenario. First, in this paper, a review of small–medium scale CHP technologies is performed, which may be fed by low temperature waste heat sources. Then, a review of the 100% RE scenario studied by researchers from the Lappeenranta University of Technology (through the so-called “LUT model”) is conducted to identify potential low temperature waste heat sources that could feed small–medium CHP technologies. Second, some possible interactions between those mentioned waste heat sources and the reviewed CHP technologies are presented through the crossing data collected from both sides. The results demonstrate that the most suitable waste heat sources for the selected CHP technologies are those related to gas turbines (heat recovery steam generator), steam turbines, and internal combustion engines. A preliminary economic analysis was also performed, which showed that the potential annual savings per unit of installed kW of the considered CHP technologies could reach EUR 255.00 and EUR 207.00 when related to power and heat production, respectively. Finally, the perspectives about the carbon footprint of the CHP/CCHP integration within the 100% renewable energy scenario were discussed.