Green’s Dictionary of Slang

to sleep, usu. in a barn or other outbuilding.

1835		Worcester Herald 26 Dec. 4/3: Where did you skipper last ranttee? [...] I did not skipper, I dos’d at a pad.
1880		Leicester Chron. 4 Sept. 9/6: He had no money; the tramp ward, at Knutsford, was five miles further on, and he determined to ‘skipper it’.
1881		Newcastle Courant 2 Dec. 6/5: Hush-hush, he’s taking a dose of the balmy, but he skippers as lightly as a mouser.
1882		Dundee Courier (Scot.) 8 Aug. 7/4: I knows a limekiln just this side of Haydon Bridge, but I shan’t skipper there [...] No more sleeping on limekilns for me!
1882		Dundee Courier (Scot.) 22 Sept. 7/4: We were forced to go to the lodging house, or run the chance of finding a place to ‘skipper’ in.
1895		Belfast News-Letter 26 Dec. 7/2: It came on to snow when we was near the ruined house, and I proposed to skipper it there.
1935		‘George Orwell’ Clergyman’s Daughter (1986) 102: I’m skipperin’ in a cow byre. [Ibid.] I wasn’t brought up to like this - ’iking and skippering like you was.
1950		P. Hoskins No Hiding Place! 192/1: Skippering. Sleeping in the open-air.