In a dewing-trouble-prevented water-proof connector assembly, its male connector is engaged with its female connector in such a manner that the front end portion of the inner housing of the male connector is engaged with the front end portion of the inner housing of the female connector in such a manner that the inner cylindrical surface of the front end portion of the male connector covers the outer cylindrical surface of the front end portion of the female connector, and the front end portion of the outer housing of the male connector is engaged with the front end portion of the outer housing of the female connector in such a manner that the front end portion of the outer housing of the male connector covers the front end portion of the outer housing of the female connector. In the connector assembly, an inner packing which is set in close contact with the inner cylindrical surface of the front end portion of the inner housing of the male connector is mounted on the outer cylindrical surface of the inner housing of the female connector, while an outer packing which is set in close contact with the inner cylindrical surface of the outer housing of the male connector is mounted on the outer cylindrical surface of the outer housing of the female connector.