LOL. Me too. I do love the holiday season.
I’ve always loved “Lo How a Rose E’er Blooming”, “The Little Drummer Boy”, “O Come O Come Emmanuel”, “The Holly and the Ivy”, “I Wonder as I Wander” “The Toy Trumpet” (The one conducted by Arthur Fiedler especially) “Carol of the Bells”, “The Coventry Carol”, and many more. I found several albums that have the songs I love. I’ll list them in order from very nice (IMO) to nice.
Sleigh Ride! Classic Christmas favorites This is the one that has the Arthur Fiedler version of the Toy Trumpet. It also has the Hallelujah Chorus on it.
A Festival of Christmas Carols Robert Shaw Chorale This one has a lot of my favorites on it. I like to sing and listen to almost every one. There are some I’m neutral on.
Ultimate Classical Christmas Album of All Time This one is a double album and is quite nice. Some of their interpretations are just okay though.
Christmas Adagios: Holiday Classics is nice too.
All of those links have sound samples on them, they are to Amazon.com pages.
Joe Pass - Six String Santa
If you are a fan of jazz guitar, this is a must-have.
Coming back to add Mannheim Steamroller’s Fresh Aire Christmas. It has a very nice interpretation of “The Holly and the Ivy” on it. Other carols I forgot to mention were “Good King Wenceslas” and “I Saw Three Ships”.
hands down
Kenny and Dolly, Christmas to Remember
Silly Christmas songs:
The Ten Pains of Christmas - Bob Rivers Twisted Radio
Blue Christmas - some guy doing a Porky Pig imitation
We Wish You a Merry Christmas - John Denver & The Muppets
Leroy the Redneck Reindeer - Joe Diffie
They Shined Up Rudolph’s Nose - Johnny Horton
More silly songs:
Santa Looked a Lot Like Daddy - Buck Owens
Christmas in Hollis - Run-DMC
I love the Porky Pig Blue Christmas one!
And as long as we’re talking Bob Rivers, “Walkin’ Round in Women’s Underwear” has to be mentioned.
Another Robert Shaw The Many Moods of Christmas
I’ve got a couple versions of the Messiah, but they’re both out of print. Still, any complete Messiah belongs in a collection. Robert Shaw’s version on Telarc was good, although I haven’t heard it in a while so I can’t say how it stacks up against the current ones in print.
I also enjoy Bach’s Christmas Oratorio
Also, a complete Nutcracker
Heck, we could devote an entire thread to Bob Rivers! 
IIIIiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiiii want a hippopotamus for Christmas!
Only a hippopotamus will do!
No crocodiles, or rhinoceroseses!
I only want hippopotamuseses…
You people may have to pay for the marriage counseling. Why? Because you forced me, forced me! to get out the Christmas cds. Oh yes.
First up? A fun favorite:Lou Rawls’s “Christmas is the Time”.
If you can resist his version of “I’ll Be Home for Christmas,” it’s just proof your soul was sucked out of you by a machine!
I love that song too! I remember having the 45 back when I was a kid.
Have a Fun Christmas has many of the great classics. The Chipmunk Song, The Singing Dogs, Twelve Days of Christmas (Bob and Doug, eh) and a great Louis Armstrong song called Zat you Santa Clause?
Great album.
There there is The Best Christmas Album in the World, EVER. 44 tracks of some really great Christmas tunes including one of my favorites I Wish it Could Be Christmas Every Day.
Aiyeee, no mention of Phil Spector’s Christmas Album yet? 
It’s not just Christmas; it’s A Toolbox Christmas!
This is very important: who is the artist on “I Wish It Could Be Christmas Every Day?” Amazon doesn’t say, and I’ve been looking for a particular version of that song since 1985 … the fact that this album is an import bodes well! I’m trying not to get my hopes up, though!
I don’t think anyone’s mentioned “In Dulci Jubilo” yet. That’s gotta be one of my favorite Christmas songs, especially when sung a capella in the original language(s). It has a nice story to it, too – it was a very, very early Christmas song. When the Reformation came along, the Protestants threw out most of the old Catholic hymns, but there were a handful that were considered so beautiful that they kept them anyways. The story may be apocryphal, but I like it anyways. The tune was adapted into the better known “Good Christian Men Rejoice.”
“Hark! the Herald Angels Sing” is another personal favorite. Little known fact: the tune was written by Felix Mendelssohn. As far as I’m aware(?), that makes it the only popular Christmas carol written by a major classical composer. (I’m not counting stuff like Handel’s Messiah – just the songs that are typically sung around the piano.)
For modern stuff, “Santa Baby” has to be one of the funniest Christmas songs out there. And a whole book has been written on the influence of “White Christmas.”
The version on The Best Christmas Album in the World, EVER is by Wizzard, headed by Roy Wood, formerly of the Electric Light Orchestera, who wrote the song.
I really like Trans Siberian Orchestra, but whenever I think of Christmas, I think of this one song my Mom found when I was little. It’s so obscure, I just found it on CD a few years ago.
The song is by Merle Haggard, and is calledSanta Claus and Popcorn.
Another good obscure one is Thistlehair the Christmas Bear by Alabama.