A while back we talked about herut חרות - "freedom". But what about the similar word chofshi חפשי - "free" and the related chofesh חופש and chufsha חופשה - which originally meant "freedom" and today have the sense of "vacation, holiday" (the former being more general, and the latter referring to a specific break from school or work)?
The etymology of the root חפש is not clear. Klein mentions an Ugaritic cognate hps - "freeman, soldier", and Kaddari brings the Akkadian hupsu. However, one of the more interesting theories connects it to the root חבש, meaning "to bind" (or in more particular usages - to saddle an animal, to dress a wound or to imprison someone.) From this root we get the word chovesh חובש - "medic" (one who bandages wounds) and machbosh מחבוש - "(military) incarceration." Klein says that perhaps even the Hebrew word for quince, chabush חבוש, has the same origin, due to its "constipating effect."
He says both senses can be understood via "the idlers who are free [from work, society] but are sealed in their homes."
I don't think that the negative connotation of chofesh remains in Hebrew today. However, the tension between "freedom from" and "freedom to" certainly exists, as any parent can tell you during the חופש הגדול chofesh hagadol - "summer vacation"...