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Berkshires are beautiful and awesome. If you really don't mind dropping some dough stay at the
Old Inn on the Green in New Marlborough... definitely the best dining you can get in the region and a nice place. I still know a few of the staff there, let me know if you are going to contact them. It's also close to various hiking and sightseeing attractions, and not far from some of the better nightlife in the area (Great Barrington).
If you stay in the Berkshires try to stay in SOUTH Berkshire county, preferably Great Barrington - Monterrey - New Marlborough - Sheffield - Stockbridge - Lee. There's an outlet center outside of Lee, best shopping other than that will be in Lee, Stockbridge, Barrington, Lenox.
There are a ton of great places to eat as well. If you're going for a week or so you might want to look into renting a house or cottage instead of a B&B, although there are lots of good B&Bs too.
My lady friend and I will be spending our anniversary at a B&B recently opened by our friend's parents in Monterey, MA in a few weeks... I'll let you know how it is, they are very good people.
NT
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Exactly what I was gonna suggest. I went to school in the Berkshires. It's AMAZINGLY beautiful in the Fall.