I was here in Woodside on 27th May for a couple of days with my family and relatives. As requested, we could get a cottage with two rooms - rooms were okay in terms of cleanliness and space. It was at a walkable distance from the central market (3/4 Km from station) without the usual hustle bustle of a marketplace. The good part of this hotel was the hospitality of the staff, the food (lunch & dinner) and garden in front of the hotel with a variety of games viz carrom, table tennis, badminton court, dart, swings etc
Not to forget the monkeys which kept us occupied. All in all a nice place to stay.
The best time to visit matheran would be during the months Oct to Jan (winter season) as summers are a bit hot and there is water & power shortage during summers.