We show that the higher-order Weyl algebras over a field of char-acteristic zero, which are formally rigid as associative algebras, can be formally deformed in a nontrivial way as hom-associative algebras. We also show that these hom-associative Weyl algebras arise naturally as hom-associative iterated differential polynomial rings, that they contain no nonzero zero divisors, are power associative only when associative, and that they are simple. We then determine their commuters, nuclei, centers, and derivations. Last, weclassify all hom-associative Weyl algebras up to isomorphism and conjecture that all nonzero homomorphisms between any two isomorphic hom-associative Weyl algebras are isomorphisms. The latter conjecture turns out to be stably equivalent to the Generalized Dixmier Conjecture, and hence also to the Jacobian Conjecture.