Seeing fall foliage is one of the best things to do in Woodstock. So naturally, everyone flocks to Vermont during this time. We booked our trip 4 months in advance, and it proved to be late. A lot of the inns and bread and breakfasts we wanted to consider were already fully booked out for our dates. So if you're serious, I would have your trip booked 6 months in advance. This will guarantee you have a chance to snag affordable accommodations. Keep in mind that Woodstock is really small, and there aren't too many inns around. Airbnb or VRBO might be something to consider too. You may also want to consider staying in Lebanon, NH and driving into Woodstock for the day.