The break was instituted last season to give the players a chance to get away from the mental and physical grind of the 82-game schedule.
Many players and coaches choose to stay home and relax, but plenty use the time to take a rare in-season vacation, usually reserved for around the All-Star Game.
For example, five New Jersey Devils players are taking their families to Orlando, Florida, for what they hope will be a relaxing getaway, even if it means chasing their kids around Disney World for a while.
Devils captain Andy Greene said he and his wife, Rachel, will be joined by forward Brian Boyle and his wife, Lauren Bedford; goalie Cory Schneider and his wife, Jill; forward Drew Stafford and his wife, Hali; and forward Marcus Johansson and his wife, Amelia Falk.
Between them, they're bringing eight kids, all under the age of 4. Greene, Schneider and Boyle each have two kids, Johansson has one. The Staffords are bringing their older son, but leaving their 9-month-old twins at home with grandparents.
"It'll be a great trip," Greene said. "We were just spit-balling what we wanted to do. There were a couple different options and that one seemed the most logical and the best."
Greene said the wives and kids flew to Orlando on Sunday, when the Devils were in the process of losing 5-4 in a shootout against the New York Islanders at Barclays Center. The players will be flying to Orlando together Monday, and everyone is returning in the evening Thursday.
Video: Nelson's SO goal rallies Islanders past Devils, 5-4
The Devils will practice Friday before playing the Philadelphia Flyers at Prudential Center on Saturday.
As for how often they'll be at Disney World, Greene said it won't be every day, because the parents want to, you know, keep some level of sanity on the trip.
"A little bit," Greene said. "We're not going every day all day, but we'll probably do one day there and then we'll just relax and let the kids have a great time."
They might see Boston Bruins goaltender Tuukka Rask, Montreal Canadiens defenseman Karl Alzner or defenseman Jonathan Ericsson of the Detroit Red Wings on the It's a Small World ride at the Magic Kingdom. Each is on his way to Orlando as well for some sun and fun.
Read on to learn about what some other NHL players are planning for their winter breaks:
Will Butcher, New Jersey Devils: "My girlfriend and I are heading up just north of West Point [New York], to Mohonk [Mountain House] resort, to just relax. One thing we both like to do is be outdoors and do outdoors stuff, so they have snowshoeing and other outdoor activities that appeal to us. So we're just going to go up there, hang out and relax for two days. All the older guys were telling me that you've got to go somewhere, take the time when you can get it."
Logan Couture, San Jose Sharks: "I'm going to Hawaii once we get back to San Jose. Flying out with some buddies."
Brandon Manning, Philadelphia Flyers: Going to head up to Vermont. Me and my girlfriend, and Valtteri [Filppula, and his wife] is going up there too. I think we'll do some dogsledding and be in the lodge. Live the ski life a little bit. It's a mountain I've never been to."
Riley Sheahan, Pittsburgh Penguins: "I'm going to go to the Bahamas. Just enjoy the sunshine a bit and re-energize myself for the [second] half of the season."
Stephen Johns, Dallas Stars: Last year we went to the beach, didn't really like it that much. This year we are going to California, renting a car and exploring the Redwood Forest.
Gabriel Landeskog, Colorado Avalanche: "Heading to Newport Beach, [California], hoping to get in some golf."
Sean Kuraly, Boston Bruins: "I'm going to hang out here and then maybe head up to Stowe [Vermont]. I've never been up to that part of the country so it should be cool."
Not everyone is ready to hit the road for the break. Many NHL players are staying closer to home, to spend time with the family, to catch up on some rest, nurse nagging injuries or recharge the batteries for the second-half sprint the regular-season finish line.
Kari Lehtonen, Dallas Stars: "Just going to be a parent. Stay at home, play with my kids, be nice to my wife."
Gustav Nyquist, Detroit Red Wings: "I'm not going anywhere. My wife has to work, so I'm stuck up here in frozen Detroit."
Justin Schultz, Pittsburgh Penguins: "I'm going to go home, back to Kelowna [British Columbia], and see some family. Recharge and get ready for the long stretch run here."
Sean Couturier, Philadelphia Flyers: "I'm going back home [to Drummondville, Quebec]. Building a house right now and see how that's going. Relax, recharge the batteries, come back better."