I had to stop DS feeding at night when he was 17mo, as I discovered I was preggers and it was just to painful. And exhausting! I'm still BFing during the day, but I'm trying to cut back to 2 feeds/day then hopefully stop by the summer (give the norks a rest before the next one arrives!)
I decided to go cold turkey, but I didn't feel bad about it as we were co-sleeping at the time.
I stayed with him until he fell asleep, giving him as much cuddles as he wants, but never lying beside him.
The fisrt night I did everything as normal before bed, but refused him boob. He screamed blue murder for 30 mins then fell asleep. He woke up a couple of times in the night, the longest session being 1 hour, when he was really upset.
Second night was OK, down within 10 mins, crying not nearly as bad. Woke 3 times in night, briefly.
Third night, went down happily, didn't even fall asleep in my arms. Slept all night.
In the past month, he has slept through 3 0r 4 times. He seems to lurch from waking a lot to only once or twice (but falling asleep very quickly).
If he asks for boob, I give him water - he'll ask maybe 2-3 times per week.
He's settled in his own room now, some nights I'll take him in our bed, others he's in his won bed all night - depends how lazy I'm feeling! He's reached the stage now that I'll sit on his bed, but he voluntarily lies down wide awake and drifts off by himself, sometimes singing which is cute.
In terms of the crying thing, it is upsetting but I had to reach the point where the thought of frequent night nursing was intolerable - I don't think I could have refused him any earlier, even at 12 mo.
BF at night becomes a habit, and the only way your DS is going to break the habit is if you refuse him. The crying that first night is awful, but as I was cuddling him it didn't bother me too much.
I don't know if this is any help?