We investigate the ground-state phase diagram of the frustrated transverse field Ising (TFI) model on the checkerboard lattice (CL), which consists of Néel, collinear, quantum paramagnet and plaquette-valence bond solid (VBS) phases. We implement a numerical simulation that is based on the recently developed unconstrained tree tensor network (TTN) ansatz, which systematically improves the accuracy over the conventional methods as it exploits the internal gauge selections. At the highly frustrated region (J2 = J1), we observe a second order phase transition from plaquette-VBS state to paramagnet phase at the critical magnetic field, Γc = 0.28, with the associated critical exponents ν = 1 and γ ≃ 0.4, which are obtained within the finite size scaling analysis on different lattice sizes N = 4 × 4, 6 × 6, 8 × 8. The stability of plaquette-VBS phase at low magnetic fields is examined by spin-spin correlation function, which verifies the presence of plaquette-VBS at J2 = J1 and rules out the existence of a Néel phase. In addition, our numerical results suggest that the transition from Néel (for J2 < J1) to plaquette-VBS phase is a deconfined phase transition. Moreover, we introduce a mapping, which renders the low-energy effective theory of TFI on CL to be the same model on J1 − J2 square lattice (SL). We show that the plaquette-VBS phase of the highly frustrated point J2 = J1 on CL is mapped to the emergent string-VBS phase on SL at J2 = 0.5J1.