Studies have shown that the proper selection of core materials in sandwich structures improves the overall structural performance in terms of bending stiffness and strength. The core materials used in such systems, such as foam, corrugated, and honeycomb, are frequently applied in aerospace engineering. However, they are a costly option for civil engineering applications. This paper investigates the bending performance of the proposed GFRP softwood sandwich beams assembled using pultruded GFRP with adhesive connection methods for potential applications in prefabricated building construction. The ultimate load capacity, load–deflection responses, failure modes, bending stiffness, load–axial-strain behaviour, and degree of composite action were experimentally evaluated. The effects of varying shear-span-to-depth ratios a/d between 2 and 6.5, as well as different timber fibre directions of the softwood core, on the overall structural performance were clarified. The results showed that changing the timber fibres’ orientation from vertical to longitudinal shifted the failure mode from a brittle to progressive process. Moreover, the adhesive bonding was able to provide full composite action until the failure occurred. Finally, numerical modelling was developed to understand failure loads, deformation, failure modes, and strain responses, and to evaluate bending stiffness and composite action. The results showed satisfactory agreement with the experiments.