Every year I generally do not play from mid-November to late-March/early-April.
Boston winters usually allow for a round or two of winter golf when there is no snow, but it's not that fun. I've been lucky enough for a couple rounds down south in Feb/March most years, but I generally do not want to spend premium golf tourist dollars when I haven't been playing...$250/rd in Florida makes no sense to barely hit the clubface, but it's fun to go down for some "Spring Training" rounds in late March/early April, although that's high-season for golf in the South.
I always shake my head at the fact that during my HS baseball years, I didn't play really at all until August when summer ball died off and I needed to prepare for HS golf team play starting just after Labor Day. Baseball was a blast, but I would've gotten better at golf much quicker if I played more during those summers, and I'm someone that went from a 30+ handicap to 22 to 12 to 6 in four years just playing in the Fall! I wasn't good enough for state junior play until I was slightly aged out, so that would've been fun to do.