It is generally known that luminous, ultra-steep spectrum radio sources are preferentially associated with massive galaxies at high redshifts. In this paper, we describe a pilot project directed at such objects to demonstrate the feasibility and importance of using the LOw-Frequency ARray (LOFAR) data to study the most distant massive galaxies undergoing formation and protoclusters. We successfully imaged four high-redshift (z > 2), high-luminosity radio galaxies with sub-arcsecond resolution, at 144 MHz, using the International LOFAR Telescope (ILT). Our targets were 4C 41.17, which we dubbed “the Anthill” galaxy (z = 3.8), as well as B2 0902+34 (z = 3.4), 4C 34.34 (z = 2.4), and 4C 43.15 (z = 2.5). We mapped their low-frequency morphologies and the spatial distributions of their low-frequency spectral indices and then compared these results with the available optical, infrared, and X-ray images. Both for the Anthill at z = 3.8 and B2 0902+34 at z = 3.4, the location of the steepest radio emission coincides with the Lyα–emitting ionized gas halo. Our pilot project demonstrates that thanks to its outstanding sensitivity and high angular resolution at low frequencies, the ILT is a unique facility for studying the co-evolution and interaction of massive galaxies, galaxy clusters, and supermassive black holes in the early Universe.