Cheshkovshchina () is a rural locality (a village) in Yenangskoye Rural Settlement, Kichmengsko-Gorodetsky District, Vologda Oblast, Russia. The population was 5 as of 2002.
Cheshkovshchina is located 40 km southeast of Kichmengsky Gorodok (the district's administrative centre) by road. Kuzminskaya is the nearest rural locality.