Four friends take a cottage vacation in the dead of winter, seeking refuge from their busy urban lives, if only for one weekend. However, the few residents who remain in the secluded cottage town of Rideau Ferry don’t seem to take kindly to strangers… From the moment they reach their destination, the visitors, a group of twenty-something artist types, are confronted by the ominous gaze of neighbouring cottagers, all of whom have no choice but to tough out the cold winter in this small, rural town. Over the course of their stay, the friends begin to uncover dark details about the inhabitants of the houses around them. After one of the friends is found mutilated on the front porch of a nearby cottage, the friends quickly discover that nothing is what it seems.

Tranna's golden-age charm veers into psychedelic absurdity in this blend of live on tape stand-up comedy and scripted material. "Tranna Wintour Is Special" gives a candid look into the real (and imaginary) world of this loveable diva.