We had a really hard time getting our daughter off of the evening bottle, it got to the point that she would not go to sleep without it and she was rapidly approaching five years old.
Thinking about it, we both knew that it wasn't really about the milk, it was more about the feeling of security she got from two places:
- Suckling
- Routine
Suckling was something that we did not want to replace directly, so we focused on routine.
We decided that replacing the routine would be better, so at bed time we all drank milk or hot chocolate from mugs with (just) a few cookies for dipping. We called it our night time picnic and we did it consistently for several weeks.
After the third or so week, we only provided a mug of milk and dunking treats to our daughter, but increased the amount of treats by a few, which we encouraged her to share with us. By this time, the bottle was long forgotten, we had fun having guessing games to see which parent earned the treat before we all went to bed. We wanted our daughter to feel some sort of control in the transition and that worked.
Now I wake up most days complaining about a mug of milk going to waste. She has a small (now more nutritious) snack an hour or so before going to bed, the bottles are now gathering dust and will soon be packed away.
Each kid is of course different, but giving them some control over what they see as a major transitional process will usually work. After all, parental diplomacy is letting the kid have your way :)