In a large mixing bowl, whip the heavy cream with an electric mixer on medium-high speed until stiff peaks form, about 3-5 minutes.
In another bowl, combine the sweetened condensed milk and vanilla extract. Mix until well combined.
Gently fold the whipped cream into the condensed milk mixture using a spatula. Be careful not to deflate the whipped cream.
Once combined, fold in the crushed chocolate sandwich cookies until evenly distributed.
Pour the mixture into a freezer-safe container and spread it evenly.
Cover the container with a lid or plastic wrap and freeze for at least 6 hours or until firm.
Before serving, let the ice cream sit at room temperature for about 5-10 minutes to soften slightly for easier scooping.