Yep. Some of the first ships that landed in Jamestown bringing colonists to permanently settle in Virginia arrived in the winter time.

John Smith accounts in one of his histories that a resupply ship arrived in January 1608. He's complaining that 30 of the people on board listed their occupation as "Gentlemen" - meaning they don't really work and have little to no useful skills. By his account, the ship has about 120 people on it.

J. Frederick Fausz wrote a book called "An Abundance of Bloodshed on Both Sides: England's First Indian War, 1609-1614" where he corroborates that account of a ship arriving January 2, 1608, although this record has only 100 people on that ship.

It usually took somewhere between 8 and 12 weeks to get from England to Virginia during the 17th century, so it's not likely that these ships began their voyage in the winter time, but it seems like an upcoming winter didn't stop British sailors from making the journey. They would have known that they were going to arrive somewhere in December and January - possibly planning for that, knowing that bringing food to a new colony during the winter could help keep them alive when food is tough to grow.