Spent a few days in the barn over New Years with my girlfriend and it was an amazing vacation. Really cannot say enough about how great the stay was and how friendly Lars was. He was always just a text away if we needed anything and was quick to respond to questions. Whatever you do be sure to read the welcome letter prior to arrival! It has some great information about the local area. Also, definitely be sure to say hello when you get there.
We were lucky enough to have a few inches of fresh snow right before our arrival so it was beautiful when we got there. The Barn was spectacular and it gives you that countryside/log cabin experience that can be hard to come by in the metropolitan Northeast. Being just 10-15 minutes from Bennington meant that it was easy for us to do some food shopping and aside from groceries, there was nothing else that the Barn lacked. The wood stove and view from the kitchen window were my two favorite aspects and I definitely recommend waking up a little early to catch the sunrise.
In addition to the Barn, Shaftsbury/Bennington is a great area. There are plenty of great places to eat at or to get things to cook if that is more your style. If you are worried about snow, the area had gotten ~6 inches of snow before our arrival but the following day the roads were pretty clear the day of check-in. There were two great ski areas that we visited. Bromley and Mount Snow. Would recommend Mount Snow since it had more trails, better amenities, and easier trails for beginners. Nonetheless, there are plenty of choices within 30 - 45 minutes of the Barn.
Would absolutely recommend a stay for a romantic getaway, ski trip, or countryside excursion.