Similarly to the Mad Kings Clocktower, Winterwonderland is a timed jumping puzzle and takes roughly 2 to 3 minutes to complete. Unlike the Clocktower however, there is an environmental effect on you called Frostbite that causes your health to deteriorate over time. If your health reaches 0 you will be transported back to the waiting area and will have to run the puzzle again.
There are a total of 3 paths to the jumping puzzle; Quaggan, Snowman and Gingerbread. I wouldn't consider that any of the paths are more difficult than the other and all are obvious in the linear route you need to take. There are some challenging elements (such as jumping on the candy canes) but for the most part, it's pain free.
Depending on which path you're allocated to, the snowflakes will appear a few moments after you land on the peppermint starting disc. The snowflakes only last for several seconds so you have to quickly run across them, following their path. If you don't jump on the snowflakes, a giant snowball will knock you off and you'll have to rejoin the waiting area.
As briefly mentioned above, the candy canes are probably the hardest part of the dungeon. They're difficulty because you're already under pressure to keep moving, but also because they are thin and easy to miss completely. I found the easiest method to jump on them was to quickly flip your camera so it looks down on you, so you're looking at the candy canes from above.
After bypassing the candy canes and jumping on a handful more snowflakes, you'll arrive on the peppermint discs. These are as easy to jump on as the snowflakes (if a little easier) based on their size but you'll still need to move quickly to avoid Frostbite taking too much health from you.
Probably the most difficult part of the jumping puzzle is the present staircase. After leaving the last peppermint disc, you'll be faced with a wall of presents. The presents will explode after a period of time forcing you to take an alternative route. I found moving in a diagonal to the right of the presents, before moving forward was the most effective, though several of my friends take the same method but to the left.
After jumping past the presents and navigating down the large candy cane, there will be a series of snowball's rolling down the hill. You'll need to avoid these at all costs or it's highly likely you will be unable to complete the jumping puzzle (you'll die from Frostbite). Luckily the snowballs are slow moving and peppermint discs are protruding from the walkway for you to step on and avoid them. Simply turn right after you exit the candy cane and follow the path upwards, using the peppermint discs along the way until you can walk past the snowballs. The only thing to be careful of is the AoE frost attacks which fall from the sky. If you're hit by it, your character will be chilled which makes avoiding the snowballs very difficult.
Once you've weaved your way past the Snowballs, you'll see on your right hand side a series of floating presents. All you need to do now is stick to the blue ones and you'll easily jump your way across and into the final present.
Wintersday Cheermeister: This achievement is automatically awarded when you complete the jumping puzzle across any of the three paths. It also provides 10 achievement points and contributes towards the Apprentice Toymaker.