Green’s Dictionary of Slang

sleeping in derelict, empty houses, barns, sleeping rough.

1835		Worcester Herald 26 Dec. 4/3: To dos, to sleep; skippering, sleeping under a hedge or hayrick.
1861		(con. 1840s–50s) H. Mayhew London Labour and London Poor III 405/2: Skippering is sleeping in barns or under hedges.
1988		J. Healy Grass Arena (1990) 122: Skippering is illegal; also rough. […].
1989		J. Morton Lowspeak.