Yes... you should definitely give it a try during winters... make sure to try Mapro Strawberry ice cream (or any for that matter) ... take good care of your health... Cheers!
It would be pleasant but not as beautiful as in July/Aug when its the peak monsoon in Maharashtra and Mahabalesh is full of clouds , rain and fountains.At this time of the year I would suggest to book a resort so sightseeing the main points and relax at the resort cool winds :)