It really depends on what time period you mean and what you understand as vacation.

I'm no medievalist, but I think that medieval pilgrimage MIGHT be seen as an analogue to vacation. People left their homes to go on a trip to a foreign place, seeing the sights as they went, taking pre-established routes. If you were an urban artisan who wanted to go on pilgrimage, you could convince your guild to take a collection to pay your way; in which case I presume their affairs would be handled by your guild. Other common people might be taken by a noble as they went on pilgrimage, in which case they'd be members of the noble's household, and so going on pilgrimage would BE their work. It's unclear how many lower-classed people like blacksmiths actually went on pilgrimage, and those who did go on pilgrimage might have been semi-vagrant, in which case they had no work to return to. (Source: Webb, Medieval European Pilgrimage p 110-113)

In Early Modern Britain (which I know better) there were a large number of holidays (national, religious, local and customary) that provided people a few days off to party. While it wasn't common for people to go incredibly far away, it WAS common for people to travel to local communities for ritual football matches, bell ringing competitions, feasts, and the like. In these times, the work of communities as a whole would be put on hold. As factory work increased, the story goes, these holidays were rationalized away. There's some suggestion from time-use studies by Voth, that this had quite a dramatic effect on the amount of hours that people worked in a year. From about 1750 to 1830, annual work hours jumped from 2200 hours a week to 3300, almost purely due to the reduction in days off! (Sources: Hans-Joachim Voth, Time and Work in England; E.P. Thompson's classic essay Time, Work Discipline and Industrial Capitalism has been superseded, but is still interesting.)

To find modern vacation like we're used to today, we have to turn to the middle of the 19th century. It's only then with the development of national railway networks that transportation is reliable enough and fast enough to allow people to leave home for a semi-extended period of time. It's also only in this period that there are large enough groups of workers and employers that workers can negotiate for time off. The classic story of this is the development of working class holidaying in Victorian Britain. Factory workers struck and bargained for a paid week-long summer holiday. They'd use this to take trains to seaside resorts with their families, often organized by holiday makers like Thomas Cook. Often whole communities would go together. Sometimes, like in Lancashire, communities would convert their traditional local holiday of Wake's Week into a paid summer vacation to the seaside. (Source: Hugh Cunningham, Time Work and Leisure.)