Many different reasons, but I think I can identify some of them:
- Owners of a business that can take time off as they like.
- People that work in a family business and have family members cover for them as they take time off.
- Seasonal business owners who make their yearly income during the warmer months and then have free time for a few months during the winter. This could be businesses like roofing companies, window washing companies, construction/landscaping, and other type of labor/contracting businesses.
- People that work in a seasonal business and have free time in the winter months
- People in the trades business. Plumbers, electricians, carpenters, carpet layers. All these types of professions have time between projects that would allow for extended time off.
- I know some firemen who get lots of vacation and time off throughout the year. They aren't rich by any means but have enough to spend in the months when they have time off.
- Company contractors. There are a lot of people that are contractors/consultants doing various work for companies. IT contractors, for example, might work on a 9 month project at an hourly rate and then have a few months in between while they are finding new work. That 9 month project can give them a nice cushion to live on and spend during their "off" time.
Most of the people in the Worker/Employee category aren't rich by any means. They spend a great deal of the year working long, hard hours and make enough money that spending a few months skiing and renting out a cabin isn't going to break the bank.
- Living off money that they saved/invested/accrued during their lifetime. This would include people in retirement.
- Absentee owners of a business who have other people running the day to day operations.
- People with inherited wealth
- People that have wealthy parents and don't work
Associated with wealth:
- People that aren't wealthy, but have access to a wealthy person's winter home. Maybe their wife is the niece of someone with a lot of money
Lots of different ways to get there. I'm sure there are many more I left off.
I, personally, am a contractor in the IT industry and work about 9-10 months out of the year. I make a pretty good hourly wage, but am by no means wealthy. I make enough in those 9-10 months to support myself for the year and have enough that I can travel or do what I want for the time I don't work. But it's all budgeted in. And it is fairly random. Some projects might go 3 months, some 6, some a year, some a couple of years. Sometimes I get winter months off, sometimes I get summer months off. It all depends on when a project ends which can vary. I've been on a 3 year project and took only 1 day off for those 3 years. If I don't go to work, I don't get paid.
Outsiders probably think that I have a lot of free time off at anytime I choose and endless amounts of money to blow. That's far from the truth. The reality is that I work long, hard hours with no days off for most of the year and am extremely frugal and budgeted so that when I do have some free time I can afford to do what I want and not be so tight with my money.
Sorry for the long post. I hope this gives some insight.