It's pretty common that for anyone looking for a "Winter getaway" anywhere in New England might be looking to do some skiing. But what if you're just looking for a cozy destination to celebrate the holiday season? As it turns out, Massachusetts has not one, or two, but three of New England's best Winter getaways for everyone.

The popular regional publication 'New England With Love' recently made its list of the Best Winter Getaways for 2023/2024. Of course, at the heart of the region is the Bay State, so you knew we would show up with some amazing Winter destinations, but where are they?

Where are Massachusetts Best Winter Getaways?

One spot that made the list is almost a staple destination for the holidays on any list. If you're in western Massachusetts, you already know it too well. That would be in southern Berkshire County in a town called Stockbridge.

  • Stockbridge
attachment-Stockbridge Aerial Shot
AFP via Getty Images
AFP via Getty Images
AFP via Getty Images
AFP via Getty Images

Stockbridge has often been known as a premiere spot in the Berkshires for its holiday celebrations this time of the year. Here's what 'New England With Love' had to say about the small town making their list:

...Nestled among the Berkshires, Stockbridge has a lot to offer, and there’s plenty in nearby towns as well. Head over to Lenox to join one of the holiday tours at Edith Wharton’s The Mount. Or, head off to the historic estate of Naumkeag, which puts on the magical Naumkeag Winter Lights for the December holidays through January.


From Stockbridge, we head to the opposite corner of the state in the northeast. In the town of Westford, you'll find another spot that made the list, which is Nashoba Valley Ski Area.

  • Nashoba Valley Ski Area

For anyone wanting to ski while not heading too far north in New England, this spot in the Bay State is perfect!

This is a super easy drive from Boston and other points south. The Nashoba Valley Ski Area is located in Westford, MA and offers 17 trails, lifts, and lessons. For non-skiers, there’s also a huge snow-tubing area. This is always fun for kids and adults alike, and there are many other family-oriented activities (check out Animal Adventures rescue center!) making this one of my favorite places for New England winter getaways with the fam.


As for the other best Winter getaway destination that made the list, perhaps it was the most obvious spot in Massachusetts. That would be over in the city of Boston.

  • Boston

Sure, it can get cold in the Winter, but that is pretty much how it will be everywhere in New England during the season. 'New England With Love' mentions how the Boston winters bring smaller crowds and lower hotel prices, along with plenty to see:

Boston in winter is likely going to focus on indoor pursuits. Might I recommend the museums and galleries? There are dozens. The science museum is one of my personal favorites, and the aquarium is always terrific, too.

If you want to get outdoors for some winter city fun, you can go ice skating at the Boston Common Frog Pond. Later, warm up at an award-winning spa and dine at a fabulous restaurant.

There are your spots for your Winter getaway this year and into 2024. Now that we're in December, the season is pretty much already here, so you might as well enjoy it at one of the best getaways for this time of year, Massachusetts!

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