Heat oven to 350°F. Butter 8-inch square baking pan. Place half the bread cubes, chocolate chips and cranberries in pan; repeat layers.
In large bowl, whisk together half-and-half, pumpkin, eggs, sugar, pumpkin pie spice and vanilla. Pour over bread mixture.
Place bread pudding pan in bottom of 13x9-inch baking pan; place in middle rack of oven. Fill larger pan halfway with boiling water. Bake 40 to 45 minutes or until knife inserted 1 inch from edge comes out clean.
Serve warm with whipped cream or ice cream. Cover and refrigerate leftovers.
