The reliable characterization of insulation materials in relevant environmental conditions is crucial, since it strongly influences the performance (e.g., thermal) of building elements. In fact, their properties may vary with the moisture content, temperature, ageing degradation, etc. Therefore, in this work, the thermomechanical behaviour of different materials was compared when subjected to accelerated ageing. Insulation materials that use recycled rubber in their composition were studied, along with others for comparison: heat-pressed rubber, rubber_cork composites, aerogel_rubber composite (developed by the authors), silica aerogel, and extruded polystyrene. The ageing cycles comprised dry-heat, humid-heat, and cold conditions as the stages, during cycles of 3 and 6 weeks. The materials’ properties after ageing were compared with the initial values. Aerogel-based materials showed superinsulation behaviour and good flexibility due to their very high porosity and reinforcement with fibres. Extruded polystyrene also had a low thermal conductivity but exhibited permanent deformation under compression. In general, the ageing conditions led to a very slight increase in the thermal conductivity, which vanished after drying of the samples in an oven, and to a decrease in Young’s moduli.