Score the bottom of peaches with an "X." Remove the skins of the peaches by dropping them in a pot of simmering water for 30 to 60 seconds. Remove the peaches, set aside to cool in a bowl of ice water and then peel off the loosened skins. Remove the pits from the peaches and then finely chop the flesh. Put the chopped peaches in a bowl.
Pour the cream into a large mixing bowl. Add a 1/4 cup sugar and the vanilla extract. Whip into soft peaks.
Cut the corn bread into thin slices. Layer the bottom of a clear glass trifle or other serving bowl with a third of the cornbread. Add a third of the peaches on top of the cornbread and then a third of the whipped cream on top of that. Repeat the layers two more times and crumble the final layer of the cornbread on top.