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I saw a native Japanese speaker post this on Twitter, I believe that おやすみ means vacation or holiday, but I was unable to figure out the phrase from the context.

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You can't understand this use of おやすみ as a combination of お and やすみ. It's an abbreviation for おやすみなさい, which is derived from お+やすみ+なさい, but has become a single word meaning "good night!" – snailplane Oct 4 '13 at 16:16
Could you share with us a link to this twitter post? – user3169 Oct 7 '13 at 17:49
I tried to dig it up, but was unable to find it. The entire text of the tweet is おやすみちゃー( ^^) – jessecurry Oct 9 '13 at 14:44
I googled "おやすみちゃー" and it seems like some people are using おやすみちゃー or おやすみちゃーい to say おやすみなさーい (probably jokingly, or to sound childlike or cute). Kids often pronounce おやすみなさい as おやすみなちゃい, and they even dropped the な. – user1016 Oct 12 '13 at 15:48
Thank you for the insight. – jessecurry Oct 14 '13 at 19:37
up vote 3 down vote accepted

やすみ means vacation or holiday. おやすみ is usually said to mean おやすみなさい, which means "good night". I don't know what the ちゃー part means. Can you provide more context (or the whole tweet itself)?

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The entire text of the tweet was おやすみちゃー( ^^) – jessecurry Oct 4 '13 at 15:45
Hmm, I have no idea then. Could be an inside slang that person uses. Like I sometimes say おじゃすみ〜ん for おやすみ. – istrasci Oct 4 '13 at 16:38
perhaps ちゃ is a dialect of [仙台]{せんだい} or [北九州]{きたきゅうしゅう} area. cf. うる星やつら 1話 うわさのラムちゃんだっちゃ youtube.com/watch?v=SLzST737yEc at 6m28s, 8m05s and so on. – jovanni Oct 14 '13 at 13:04

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