Place 12 cookies in the blender and add the milk. Blend until fully combine. Add the cream, sugar, salt and vanilla. Blend again until the mixture is smooth. Pour into the ice cream maker and freeze according to the manufacturer's directions.
While the ice cream is churning, chop or quarter the remaining cookies into bite-sized pieces.
When the ice cream has finished churning, scoop about a third of the ice cream into a freezer safe container and scatter a handful of chopped cookies over it. Repeat with more ice cream and more cookies layering the ice cream and cookies into the container. Freeze until firm and scoop-able.