If you hate cuteness and/or romance in anime, I can guarantee you'll hate Winter Garden, because it's...well, a cute romance story. The main characters are Dejiko, who's 20 now, her younger sister Puchiko, who's 15 and lives with Dejiko, and Takurou, the guy Dejiko meets by chance on Christmas and becomes interested in. Dejiko and Puchiko are characters from Di Gi Charat, but since I've only seen one episode of it, that didn't mean much to me--if you'd watched Di Gi Charat you'd doubtlessly find more references and in-jokes that would've blown right by me.
The characters really make or break most anime for me, and Winter Garden has a very likeable cast--Dejiko's hard not to root for, she's innocent and a little ditzy, while Puchiko has the ability to tease her older sister down perfectly, and the interactions between the two are some of the best parts of the OVA. Puchiko's character is just awesome, and Dejiko's reactions to her comments are pretty funny. Puchiko gets to play the guitar in the second episode, although if like me you were hoping for something along the lines of Lost My Music, it's going to disappoint you--damn you, Kyoani, for setting such a high bar to clear for concert scenes. The character designs in Winter Garden are simple, but really cute, reminding me a lot of Snow Fairy Sugar. It's not jaw-dropping animation like the ball scene in Kyoani's Kanon, but it's not Cabbage Love either--the characters are drawn consistently well, the backgrounds are good, and the atmosphere fits the story perfectly.
Hinano already has an excellent summary of the plot (ep 1 and ep 2), but to put it in a single sentence, the plot is boy-meets-girl, misunderstanding between boy and girl (of course), and (as you can probably guess from a mile away) the misunderstanding gets cleared up at the end. The ending's not entirely conclusive (you don't see Dejiko get married or anything) but you can fill in what happens from there easily enough. It's nothing groundbreaking, but it's still a well-told story, it's cute, and hell, it's better than the allegedly heartwarming crap they show on US TV around Christmastime. I can definitely see myself watching it again next Christmas, or anytime I'm just looking to watch something that'll put a smile on my face. Although it's only two episodes, if it shows up on region 1 DVD, I'll buy it in a second, since I'm a sucker for shows like this.
On a side note, I really wish they would do this with Galaxy Angel--take the characters a few years down the road and put them in a romance-type story like this one. There were a couple serious epsiodes sprinkled throughout Galaxy Angel's run, but I'd love to see something like Winter Garden done with the cast, in an alternate universe or what have you. The second season of GA kind of went that way in one episode as I recall, but Milfeulle x Volcott? Ugh.
On a side, side note: between Winter Garden and Kanon, I'm really starting to miss snow. I'm sure I wouldn't miss it if I had to shovel out my driveway, but sitting here when it's 63 degrees Fahrenheit outside I'm just not feeling that winter atmosphere. But before everyone who lives in colder climates starts throwing e-snowballs at me, wishing it was anywhere near 63 where they are, I should probably shut up.