Winnie is the English diminutive of Winifred — from the Old Welsh Gwenfrewi ("holy peace, blessed"). Winnie-the-Pooh — A. A. Saint Winifred — Welsh medieval saint.
Winnie does not currently appear in the US Social Security Administration's top 1,000 girls' names, so we don't publish a US rank or birth count for it. That says nothing about the name's standing elsewhere in the world — only that it sits outside the ranked US data we rely on.
In Pythagorean numerology the letters of Winnie reduce to 2, The Peacemaker. This is a traditional interpretive system, not a factual claim about the name.