I visited Mahableshwar just last week (week before Christmas) and really enjoyed it. It is the strawberry season (although you do get them throughout the year) and really gorged on strawberries.
I and my family (husband and kid) stayed at Brightlands Holiday Village. I found that this hotel is the most expensive (1600 per person per day without food) in Mahableshwar. It is not really worth it since you spend most of the day outside. Stay here only if you like swimming (they have a nice swimming pool) and have a lot of money to spend. They also have a nice discotheque. Also, the service is good. If you dont really care about the above things, stay at other hotels like Vimal Gardens, Shreyas etc. which are cheap and really value for money. We had only one meal at Brightlands. Even the food was too expensive. Also, you get better food elsewhere. Try Grapevine on Masjid road for great Parsi and Thai food. Also try VG’s restaurant for cheap Parsi food (the Dhansak is great!).
I really liked horse-riding at the Polo ground and boating on Venna lake. However, they are enlarging the lake and the lake does not look as good as it did two years ago due to the construction work going on. Still, do go for a boat ride. While at the lake do not miss the veg. frankies and the strawberry with cream available near the lake. Yummy.
Do go to Panchgani and visit Century Sherbaug if you have kids. It gives them a nice exposure to nature. It has a very beautiful rose garden (much better than Mapros) and also lots of birds like turkeys and swans which the kids can mingle with. They also have animals like rabbits etc. There is also a nice childrens park.
Do NOT go to the table land unless you like horse riding. There is nothing there except a vast dusty area. Nothing much to see.
I do not recommend seeing a lot of points unless you are the trekking type (I enjoy trekking but with a small kid, its impossible). The must-see points are Kates point, Elephant point and Parsi point.
Seeing the Mapro factory etc. is a waste of time. Also, buying all the jams etc. is o.k. but the quality is not so good. The only thing is that you get a variety of flavors. Quality is so-so.
I do recommend Wilson’s chocolate walnut fudge that you get in the market. Window shopping at the market is fun.
Overall, I think that the best thing is to relax, eat good food at Grapevine etc. and enjoy the great weather and the strawberries. Do not spend a lot of time in watching points etc.
Do take woollens in winter since it gets chilly in the evenings.