We discuss the rolling, without slipping and without twisting, of Stiefel manifolds equipped with α-metrics, from an intrinsic and an extrinsic point of view. We, however, start with a more general perspective, namely, by investigating the intrinsic rolling of normal naturally reductive homogeneous spaces. This gives evidence as to why a seemingly straightforward generalization of the intrinsic rolling of symmetric spaces to normal naturally reductive homogeneous spaces is not possible, in general. For a given control curve, we derive a system of explicit time-variant ODEs whose solutions describe the desired rolling. These findings are applied to obtain the intrinsic rolling of Stiefel manifolds, which is then extended to an extrinsic one. Moreover, explicit solutions of the kinematic equations are obtained, provided that the development curve is the projection of a not necessarily horizontal one-parameter subgroup. In addition, our results are put into perspective with examples of the rolling Stiefel manifolds known from the literature.