In the bowl of a stand mixer fitted with a whisk attachment, whip the heavy cream until it holds stiff peaks. Slowly drizzle in the sweetened condensed milk until it's completely incorporated.
Once the mixture is thick and fluffy, beat in the vanilla extract and the ⅓ cup of peanut butter. Mix until smooth.
Grab a 9x5 loaf pan {or other suitable ice cream container}, and pour in half of the ice cream mixture. Using a spoon, drop small dollops of peanut butter on top, and add about half the crushed cookies. Using a knife, gently swirl the peanut butter and cookies into the ice cream base.
Add in the remaining ice cream, and repeat.
Cover tightly with plastic wrap, and freeze for at least 6 hours. Enjoy!