Phil mentioned the Gray Ghost Inn (and Kitzhof Inn). I have stayed at GGI several times and can endorse it enthusiastically. Not overly fancy, but warm, welcoming and rider friendly. Breakfast included, and if there is a large enough group, a special dinner could be arranged. Lots of room to hang out, swimming pool and an excellent front porch and rear deck.
It is in a great riding area, right on VT Rt 100 near Mount Snow in West Dover, VT. Bennington is about a 45 minute ride and of course you have all of Rt 100 and several "over the mountains" routes to choose from.
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