We rented this house for our wedding weekend, to stay in with all of our friends of honor. It felt exactly like having an entire old-style bed and breakfast to ourselves. Every bedroom was cozy and lovely, and each was well-suited to a couple, with some having space for an extra person as well. There were ample bathrooms for everyone. The kitchen was great for cooking for a large group. We were able to serve dinner for about 20 people (some of whom were staying at a different house) one evening. There was so much space to hang out that even with that many people in it, it never felt crowded, and there was plenty of room for privacy and for multiple small groups to hang out separately as well. There is a big backyard to spend time in as well. The location is a short drive to the center of Great Barrington, which has shops, grocery stores, restaurants, etc., but the house definitely feels like you're in the country. The owners were very responsive to questions and helpful.
The house feels old and funky and interesting, with lots of old photographs, taxidermy, and other historic touches. I would note that if you have severe dust allergies or asthma, this is probably not a good fit for you -- there is a old of old upholstery (including upholstered walls in several of the bedrooms) which is just inherently going to hold onto dust. However, the house is clean and well cared-for overall. There were plenty of clean towels, linens, etc. for a large group. Many of the bedrooms have window AC units, although even in August we really didn't need them.
Overall, this is a cozy, fun, and spacious house ideal for a large group!