There are so many fun places to travel in the winter with kids. From holiday break to a few long weekends in the winter, there’s plenty of time off for a little adventure. The past few years we’ve been trying to take the kid skiing at least once, because it’s something we hope they will all eventually be able to do and enjoy. We’re not quite ready to take them out west for a “big” ski trip just yet and have kept our sights on drivable ski destinations from NJ. After a few years of travel and much research for the upcoming winter, I’m sharing some great ski and winter house rentals all an easy drive from the NJ/NY area.

We’re looking at vacation home rentals for winter travel. We use VRBO/ HomeAway for vacation rentals and have always been really impressed with the quality and amount of space we get for the cost. From more space to a kitchen, renting a home is key for family travel. For a list of the 5 reasons I recommend a vacation rental for family ski trips, visit this post. I’m still narrowing down which location we’ll book but browsing winter town, houses and activities is one of my favorite things to do.

All of the destinations are about 4 hours or less from the NY/ NJ area. All have somewhere to ski nearby (most have more than one mountain to choose from too!).

Great Drivable Ski Destinations

Winter Houses to rent in VERMONT:

We’ve skied in Vermont with the kids the past two winters and had the best time. There are many VT mountains further north, but we love the ease of getting to Southern VT for weekend trips. These houses are near Windham, Mt. Snow and Stratton, two awesome mountains for kids:

Stratton Beautiful Large Ski House VRBO Rental

Stratton Condo VRBO Rental

Windham, VT VRBO Rental

Mt. Snow Vacation Rental

Winter Houses to rent in MASSACHUSETTS:

My parents took us up to the Berkshires in MA one winter as kids and we had a great family trip. It’s been on my list for a while and I think we might try and check it out this year. I have heard that Butternut is a great mountain for families.

Stockbridge VRBO Cabin

Swiss Chalet Style VRBO Ski House

Cozy VRBO Cottage on a Lake

Rustic Winter Cabin

And Super Cool Rental for a Group

Winter Vacation Homes in New York State:

If you’re in NJ and NY, you don’t have to go to far for a ski weekend or even if you’re not going to ski, these locations are wintery, cozy and fun for kids. In NY there are the Catskill Mountains, Hunter, and Adirondack Mountains for easy drivable destinations for a weekend. Here are a few vacation rentals we like in NY:

Now that you’re excited or winter travel, here are details on an AMAZING ski sweepstakes that VRBO has going on right now: VRBO’s Win the Mountain Sweepstakes where one lucky winner will win the ultimate ski trip for 20 people. They’ll get the whole mountain to themselves for the day! VRBO partnered with Eagle Point Resort in Beaver, Utah to offer this prize package including private ski instruction, a $5,000 travel stipend and three nights in this magnificent slopeside mansion. Click here for all the details and TO ENTER!