A few years ago we did a self-guided tour of central Vermont in early October with Inn To Inn Tours:
http://www.inntoinn.com/
It was great. You call them up, tell them when you want to ride & approximate daily mileage. They book the inns, provide a route with detailed maps and carry your gear to each inn. During the day, you are on your own.
The guy that runs it is a cyclist & he picks bike friendly routes. Breakfasts & dinners at each inn are included.
It was great. I would do it again tomorrow. I wish this sort of tour was available in other areas of the country.