Who were your guests during the summer? Tourists and vacationers or some other type of traveler? Where is your listing located? On the shore or inland? In a destination city or a suburb? How many other Air rooms are near you, what do they charge and what is their approximate occupancy? The answers to all these questions should give you some idea as to what to expect over the winter.
We opened our Airbnb room this past July and were booked nearly solid through July and August. That being said, we live in southern Maine, very near the coast in a summer resort town, so we expected bookings to drop dramatically after Labor Day, and indeed they have. Just weekends in September and so far we only have 6 days booked in October. I don’t expect any more bookings until late May of next year.
Given you’re also in New England, I think you will experience a slow winter as well, but perhaps not totally dead like it will be for us. Do you live near any major winter attractions, such as a ski resort? You can add all the winter activities to your listing you want, but unless people are already thinking of your area as a destination, I don’t think it will do much good.