In recent weeks I have been reworking my Winter playlist since a friend asked me if I had one to share. It is basically my pre-Thanksgiving/early December playlist, with unconventional holiday tunes, and songs focused on snow, winter, etc. as well as some obscure Christmas tunes. So no Silver Bells on this list, but Joni Mitchell's "River" is perfect, as is Elvis Costello's "I Felt The Chill Before the Winter Came".
Years ago, I used to do music swaps throughout the year with friends, and there was always a winter or holiday-themed swap where we would share our favorites to find new music to enjoy. But now CD's are so 2010, and instead I like to use streaming services to discover new music and share playlists. It's been fun revisiting my list and adding some new gems to love. (and if you're interested, here is my always-a-work-in-progress Winter playlist this year)
Google Play Music - All Access (a mouthful!). I have been on it since pretty much when All Access was launched, and it has been phenomenal. The service is well worth the cost monthly for what it affords me. It is primarily used through your browser, though there are apps (more on that later). I can add albums to my "collection" without owning them--they just go to my library and are listed among my preferred albums. I can listen to most new music/albums the day they come out, in their entirety, without having to decide to buy it. I can make playlists just like iTunes (though I hope they implement folders soon, because I have a LOT of playlists so it's a little unwieldy), and I can share those lists socially with friends.