The purpose of this article is twofold. Firstly, we address and completely solve the following question: Let (X, L) be a smooth, hyperelliptic polarized variety and let varphi : X longrightarrow Y subset textbf{P}^N be the morphism induced by |L|; when does varphi deform to a birational map? Secondly, we introduce the notion of “generalized hyperelliptic varieties” and carry out a study of their deformations. Regarding the first topic, we settle the non trivial, open cases of (X, L) being Fano-K3 and of (X, L) having dimension m ge 2, sectional genus g and L^m=2g. This was not addressed by Fujita in his study of hyperelliptic polarized varieties and requires the introduction of new methods and techniques to handle it. In the Fano-K3 case, all deformations of (X, L) are again hyperelliptic except if Y is a hyperquadric. By contrast, in the L^m=2g case, with one exception, a general deformation of varphi is a finite birational morphism. This is especially interesting and unexpected because, in the light of earlier results, varphi rarely deforms to a birational morphism when Y is a rational variety, as is our case. The Fano-K3 case contrasts with canonical morphisms of hyperelliptic curves and with hyperelliptic K3 surfaces of genus g ge 3. Regarding the second topic, we completely answer the question for generalized hyperelliptic polarized Fano and Calabi–Yau varieties. For generalized hyperelliptic varieties of general type we do this in even greater generality, since our result holds for Y toric. Standard methods in deformation theory do not work in the present setting. Thus, to settle these long standing open questions, we bring in new ideas and techniques building on those introduced by the authors concerning deformations of finite morphisms and the existence and smoothings of certain multiple structures. We also prove a new general result on unobstructedness of morphisms that factor through a double cover and apply it to the case of generalized hyperelliptic varieties.