Here’s how I install a bathroom exhaust vent in the winter. This project requires an insulated 4″ duct, a vent hood kit, and a 4-1/4″ hole through my vinyl siding.

Preparing to install a vent in vinyl siding in freezing weather.
First I drill a 4-1/4″ hole with Milwaukee M18 Drill Driver.  The hole saw works best if switched in reverse position to prevent damage to the siding.  Switch the drill to the forward position to drill through the wood.
Using Milwaukee M18 Impact Driver to install screws in the vent cover.
Final results of a properly installed bath exhaust vent in vinyl siding.
LINKS TO TOOLS AT THE HOME DEPOT:
MILWAUKEE M18 DRILL & IMPACT KIT: https://homedepot.sjv.io/c/1241924/14…
MILWAUKEE 4-1/4″ HOLE SAW: https://homedepot.sjv.io/kjn3RM
MILWAUKEE M12 INSTALLATION DRILL DRIVER: https://homedepot.sjv.io/e4oMRg
4″ INSULATED FLEXIBLE DUCT: https://homedepot.sjv.io/Jr30qQ