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@DillonLion: I think it depends on your grade/subject area but I do little to no planning over the summer. I will, however, be working on my master's this summer. I have been teaching the same subject for the past 7 years, so I do very little planning at this stage. We are moving to a new (undecided) curriculum next year, so that will require more time but I will probably just do most of my planning during my prep.
I will say, that my first couple years were nutty and full of lesson planning. Once I got my own rhythm, though, things calmed down a lot.
Best of luck to you!

I work in higher ed so it's probably different, but I still have to do quite a bit of advising, supervising internships during the summer even though I'm not on contract. It is nice though bc for the most part I can do these on my time and don't have to physically be on campus much

My husband teaches HS and does some planning work over the summer but he gets paid to do it at the school. It's minimal though - maybe a handful of days in late summer. He also has done some tutoring in the past.

During the shorter breaks, I usually work about half the break, doing grading and planning. This gives me a bit more flexibility in the following weeks.

Over the summer, for the first couple days I read over my student surveys and clean out / organize my electronic teaching files. I find this a helpful way to "de-celerate" and close the school year. Then, about 1-2 weeks before teacher in-service begins, I do this:
- Map out my units based on the school calendar and pacing guide
- Revise my letter to parents and syllabus
- Write my 1st wk plan & submit supply request
- Organize & copy materials
- Set up about half of my classroom (we don't normally get enough time to do this in teacher inservice)

It usually only takes about 1 week but sometimes I start 2 weeks early because I start having back to school nightmares about being unprepared.

Some years I have also taught summer school, too. Summer school in my district is two to three weeks, half days.

I try to enjoy summer as much as I can!
I bring home my files and lesson plans and will go over them!
My team will usually plan a bit a few days over the summer, but that is us, we like to be a little ahead when we return! In our district there are PD conferences scheduled but none are mandatory!

I taught elementary for a long time and didn't work much over the summer. I'd take a course/seminar here or there, but nothing super intensive. I also didn't lesson plan. I do like @DesertDreams88: and spend the first week of break wrapping things up and organizing some files. Then about 2 weeks before school I'd start preparing things like updating my back to school night info or creating a new layout for/decorating my classroom.
Honestly, any work I did was purely for my own fun. I enjoyed shopping for back to school supplies or coming up with a decorating theme or organizing my clasroom library with a color-coded AR labeling system. But I didn't really need to do any of that stuff.

I think its more realistic to plan that your break will end sooner than your official start date because you'll want to get physically into your classroom and prep for that first week back. I felt no guilt in really relaxing for those other weeks; I worked my tail off during the school year!

ETA: other breaks (winter, spring, thanksgiving, etc) were maybe 1/2 reluding and 1/2 work because I still needed to grade, plan, and prep.

Breaks other than summer often are spent doing some grading, planning etc but most of the summer is mine. I have to go back a little early to get my classroom ready and start planning and we have to do about a week's worth of professional development off contract time so I try to do that over the summer too.

I teach elementary school so this may not be the same for you:
Shorter breaks- a mix of relaxing, grading and lesson planning. report cards and comments are usually do around spring break so that can be time consuming.
Summer break- July is usually spent predominately relaxing. My district offers great pd, so I usually take some classes over the summer and typically I lead a workshop as well. I also work on curriculum committees that I am paid for. At the end of the school year we have to pack away all of our stuff so the rooms can be cleaned and waxed, so two-three days a week in August are typically spent unpacking, reogranizing, decorating, etc.

I keep my son home with me in the summer and send him for drop-in daycare days when I need to do work.

Summer time is sweet sweet glorious freedom! I am actually working on another degree so I focus on that but I take lots of time for myself- working out, home projects, errands, organizing, etc. And we go away, this summer it will be for four weeks (2 up north at my mom's house in the country, 2 in Cape Cod). I would go ahead and say that summer vacation is the BEST part of being a teacher, haha!