Dean:
Dean grudgingly goes out to play in the snow with you but you just end up walking around and gazing at the beauty of it all.
Sam:
He's the one to wake you super early when it's snowing outside. Rather than being annoyed by being woken up, you get dressed excitedly and go out outside to build snowmen, make snow angels, and throw snowballs.
Cas:
You usually drag Cas outside extremely early in the morning despite his protests that there is work to do. You go into town when no one is awake and just walk around aimlessly. It's especially nice when the only thing being heard is the sound of animals and your breathing.
Crowley:
You don't see Crowley as often as you would like, but he usually makes time to come see you. Especially during the winter as he knows Christmas is your favorite holiday. He absolutely refuses to go outside and act like a child so instead you two sit inside together, chatting the night away.
Gabriel:
You two go outside and mess around for a while, having snowball fights, making snow angels and snowmen, just whatever. Later on, you two go inside for hot chocolate with marshmallows of course. You bake cookies together and you only get a few because Gabriel eats the rest of them. After, he takes you out to see the sights. You fly all over the country and even make a few stops in places like Ireland and France. After everything, you go back home to watch Christmas movies together.
Kevin:
You and Kevin like to spend the whole day together, just cuddling together in the warmth of the bunker.