Thaddeus Clapp House

Outstanding was my favorite place, but it has closed, someone told me. The owner was a big feature of the place, so without her it wouldn’t be the same if they re-​open. Have stayed here for years.

I stayed here with my boyfriend when we had planned a ski weekend to Jiminy Peak which is right about 20 minutes from Pittsfield-​so super close. Firstly, downtown Pittsfield is walking distance from the B&B…only about 1 block away. Pittsfield is a cute town, lots of restaurants etc. bars if you want to go out and ski during the day.
Now for the B&B. The rooms are super nice. King size bed, separate room with a tv and electric fire place in every suite. Kitchen area including, beverages, wine, etc. Full bath. The house is the old Clapp mansion so it’s really interesting and historical on it’s own. All renovated but still an old school mansion. Rebecca the woman who owns the place is awesome. She cooks breakfast in the morning and it’s delicious. She made french toast croissants when I was there, sooo tasty. Extremely accommodating, great experience overall. Would definitely stay there anytime I was back to Jiminy Peak for a ski trip.

I need to have additional stars just to give them to this gem of a bed-​and-​breakfast. I rave about it to anyone who will listen, and for good reason. Pete and I headed back here again to celebrate our anniversary, and Rebecca the innkeeper was amazing and understanding when we had to juggle our reservation back and forth a few times to accomodate flight times. When we arrived, barely minutes before the skies opened up and the snow poured down, we found a lovely note from Rebecca explaining that she had moved us from our reserved room to the «most romantic suite in the house.» And it exceeded all of our expectations! Huge king-​size bed, gas fireplace with a little sitting area, a kitchen area with mini-​fridge and the complimentary sodas, water, and port, and of course the huge bathroom with bathrobes and towels galore. We were in heaven, able to curl up in front of the fire sipping port while the world fell away under the snow.
Pittsfield’s main street is minutes away walking, so even when we were still being shoveled out, we were able to walk into town to eat and pick up supplies. Rebecca is, as ever, full of helpful information and entertaining stories about the local history, past and present. She provides a great breakfast in the morning, even with the house full of guests, and is very attentive. This is hands-​down the best place to stay in the Berkshires.

Excellent location, helpful innkeeper, nice facilities.
A great place to stay for an overnight or a couple of days in Pittsfield, fast becoming its own little arts and entertainment center. You can walk to numerous restaurants, theatres and museums and stroll around tree-​lined streets with lovely homes in a variety of architectural styles.
The décor is nicely done: comfortable, but not overwhelming.
Plenty of hot water and water pressure in the shower, not always the case in older houses!

My girlfriend and I went here a year ago and still fondly remember this fantastic spot. Moderately priced in a land of overpriced B&Bs, but with gorgeous rooms (suites, really), great complementary breakfast and a helpful, outgoing proprietor. There is even a complimentary bottle of brandy for you to sip before hopping into the great big four-​poster bed.
The location is perfect — 5 minutes walk to a bar with great cider, within 10 minutes wandering of good Thai and Indian food. We’re both young but I’d recommend this place for any age group or budget.

The location of this B&B at the center of Pittsfield isn’t the most tranquil or scenic of locations for a B&B, but it is certainly convenient for a trip to the Berkshires. Major area attractions are only about a half hour in any direction and the house is situated on a quieter street, so the bustle of Pittsfield town center isn’t really an issue.
The suites are spacious with large living areas, plenty of closet space and even a complimentary wet bar. The innkeeper is friendly and extremely knowledgeable about the area. There’s almost nothing she can’t help with and she’s happy to sit down with you after making you some pancakes and sausages, to help plan your day.

I didn’t remember the name of this B&B five years later, but I did remember Rebecca the innkeeper and the breakfast she served — honeybaked ham, pancakes, fresh oj and fruit, and well-​brewed coffee.
I also remember how comfy the king size bed was, the claw-​footed tub, and how historic the mansion felt — i.e., a possible ghost in our room.
The bottom-​line: this place is a diamond-​in-​the-​rough of Pittsfield.