Personally the only reason I used to prefer Summer was because in middle and high school I got (on average) two weeks for break. I say on average because in middle school the break amount changed every year:
1. 5th Grade- two weeks
2. 6th Grade- week and three days and a half (got out half day that Tuesday, got Wed, Thurs, Fri off)
3. 7th Grade- week and a day and a half (had a half day that Thursday, got Christmas Eve off, Christmas was on a Saturday, so was New Years)
4. 8th Grade- one week (Christmas was on a sunday that year and so was New Years so they just gave us a half day the preceding Friday and gave us a week off)
Why the drastic change? Because we got a new principal who thought the reason we did so poorly on Midterms was because the tests were before the break and that the break was too long. So the week right after the break ended (the first week of January), we had midterms. This actually applied to high school too except we got two weeks every year.

Now with college I get like a whole month and it's nice. Sure our summer is shorter than most colleges (still longer than what I'm used to) but I don't mind in the slightest! Why? Because with summer I have to be productive because it is three months, so I have to get a job or take a class, etc. Winter Break is when I really get to chill because you can't do anything super productive in a month according to my parents.