Our Favorite New England Winter Getaways

Winter Getaways in New England - The Boston Day Book

Is it just me or are you having a hard time keeping warm, too? It’s the time of year where I think everyone is mutually craving a getaway… even if it is to another cold locale. It just feels good to shake things up and do something different. (Also, warm socks always help.)

Here are a few of our favorite winter getaways in New England. Bonus points for being able to drive, and saving money so that you can stay somewhere nicer and drink more wine. :)

Vermont Weekend Getaway


We love Woodstock (as evidenced here and here), and it makes a fabulous winter getaway whether you ski or not. Stay at the Woodstock Inn & Resort and take advantage of the beautiful and cozy spa. There is also a sauna and outdoor hot tub!

Another great spot, not far from Woodstock is Killington. I have only been skiing twice, and one of the times was at Killington when I was there for the Life is Good festival.

Have you been to The Pitcher Inn? This Mad River Valley Relais & Chateaux property is high on our wish list. How inviting does this suite look?


If I am being honest, Maine might be my favorite New England state. I love the coastline, and there are so many beautiful towns scattered throughout the state. As you may recall, we spent a week in Bailey Island this fall. I have never been in the winter, but I’d imagine it would be so charming and quiet. I would pack plenty of bath salts and bring an extra plush pair of slippers from home for lazy days.

Hidden Pond is another location that has been on my list for awhile now. And I have heard that it is a great place to bring kids. Kennebunkport is so pretty. Although most people would consider visiting in the summer months, we love to check out these kinds of places in the off-season. Usually you can find better rates and the atmosphere is more laid-back.


Just 45 minutes north of Boston, Salem is a fun weekend destination. Two winters ago, Laura and I stayed overnight at Lark Hotel’s The Merchant in downtown Salem. It was a snowy weekend and the hotel was so cozy. We ordered takeout Indian food for dinner and enjoyed it by the roaring fire. Sometimes it is nice to have a change of scenery without having to travel too far.

Are you headed anywhere fun this winter? What are your favorite winter New England destinations?

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