Indentation of a thin elastic film attached through an interlayer to a rigid support is studied. Because the common interpretations of depth-sensing indentation tests are not applicable to such structured coatings, usually various approximating functions are employed to take into account influence of the interlayer. Contrary to the common approaches, a strict mathematical approach is applied here to study the problems under consideration assuming that the thickness of the two-layer structure is much less than characteristic dimension of the region of contact between the indenter and the coating. A simple derivation of asymptotic relations for displacements and stresses is presented. It is shown that often the leading term approximation to the non-adhesive contact problems is equivalent to contact problem for a Winkler-Fuss elastic foundation with an effective elastic constant. Because the contact between the indenter and the film at nanoscale may be greatly affected by adhesion, the adhesive problem for these bilayer coatings is studied in the framework of the JKR (Johnson, Kendall, and Roberts) theory of adhesion. Assuming the indenter shape near the tip has some deviation from its nominal shape and using the leading term approximation of the layered coatings, the explicit expressions are derived for the values of the pull-off force and for the corresponding critical contact radius of adhesive contact region.