Cross-laminated timber (CLT) has become popular as a construction material and the design of CLT connections is typically based on empirical equations with an average embedment strength of the wood-based product. The experimental study presented herein aims at enhancing the understanding of the relationship between the CLT embedment behaviour and the single layers it is composed of. Non-linear embedment stress–displacement relationships were measured in 244 full-hole and half-hole embedment tests on structural timber boards as well as on CLT produced of parts of the same boards. Three different fasteners, namely a steel dowel with a diameter of 12 mm and the threaded part of screws with a nominal diameter of 6.5 mm and 10 mm, were studied. The design of the experiments allowed to validate a simple mechanical model with parallel springs for the CLT, which showed good agreement with experiments. In addition to a validation of the non-linear spring model, this unique experimental data-set is further exploited in a comparison with empirical equations and for the derivation of a non-linear embedment ratio, between parallel and perpendicular to the grain embedment stresses, over the displacement. Knowledge of the relationship between the non-linear embedment behaviour of the single layers and the CLT element can be further exploited in the engineering design and numerical modelling of CLT connections with dowel-type fasteners.