The interfacial polymer in nanocomposites (PNCs) is widely believed to exhibit modified dynamics and structure, which are considered responsible for the improved PNC properties. Owing to its high resolving power, broadband dielectric spectroscopy (BDS) is one among the most suitable tools for studying polymer dynamics. Here, BDS combined with differential scanning calorimetry (DSC), microscopy, infrared spectroscopy, and thermally stimulated depolarization currents (TSDC) are employed to study low-molecular weight polydimethylsiloxane (PDMS) and a slightly modified siloxane, polyethylhydrosiloxane (PEHS), in bulk and in the form of silica− polymer "core−shell"-type PNCs. The dielectric/calorimetric mapping for the systems based on PEHS is demonstrated for the first time. Bulk-like dynamics (α relaxation, glass transition) is recorded faster and less cooperative in the PNCs, in agreement between the techniques, most probably due to spatial confinement between the neighboring nanoparticles. The constraints arising from the particle−polymer interactions resulted in the formation of an interfacial polymer fraction, being rigid and similar in amount for the two polymers in DSC, whereas a part of this latter amount (e.g. tails and loops) exhibits retarded dynamics in BDS and TSDC. The interfacial polymer dynamics is recorded individually via the α int relaxation next to α in the PNCs. For PEHS, α int is quite weak showing a non cooperative character (sparsely distributed short tails), while it is strong exhibiting low cooperativity for PDMS (loops and tails). Because both polymers consist of small chains and exhibit similar flexibility, it is concluded that the differences in α int arise from the type and the extent of interfacial interactions, for example, the additional covalent bonding in silica/PEHS leading to the formation of many immobile trains. Finally, the absolute differences in the relaxation times between the α and α int were found similar for PEHS and PDMS, which, interestingly, suggests a "coupling" between the polymer structure and its dynamics in the bulk (unconstrained) and interfacial (constrained) state.