Dowel and screw connections in timber structures behave nonlinearly, even at loads which would be experienced in a structure in normal service. They exhibit hysteresis and creep as a result of both the viscoelastic behaviour of the timber itself and the frictional interaction between the timber and connecting elements, and stress concentrations are created which behave plastically, even at loads well below the nominal yield force of the connection. A fundamental process in the load transfer through such a connection is the embedment of the connector into the timber that surrounds it, and the frictional, nonlinear and time-dependent properties in that process are investigated here. A simple rheological model, a combination of Kelvin–Voigt viscoelastic elements, was fitted to the measured response of a block of timber in embedment by a plain dowel or screw. Experiments were performed in which an oscillating force was applied to the screw or dowel, representative of in-service vibration in a timber structure. The effects of plasticity and viscoelasticity were quantified by comparing equivalent linear stiffnesses for an oscillating load, a short-term change in static load, and an initial static loading. The results showed a stiffness, on average, 3.8 times higher under oscillating load than under initial static loading with the same peak force. By quantifying and modelling viscoelastic behaviour in timber around a connector, this work contributes to the development of damping and stiffness models for joints under oscillating load. Such models could be used to determine the contribution of connections to the dynamic response of long spans and tall buildings in timber.