Search Chalets in Pittsfield

"The Woodstock Inn & Resort is the quintessential New England inn. Walk in the lobby and you are greeted by a large warm fire. The staff at all levels were gracious and helpful. The room was large, well decorated and extremely comfortable. Great location to walk downtown even with single digit temperatures. The shops were expensive but worth browsing & buying. "

"Rooms and bedding were very comfortable. Staff was busy throughout the day keeping the pool and rooms clean. Pool and Hot tub are more than adequate for kids and adults. Just 30min drive to Okemo for good skiing. Many restaurants and activities all within walking distance."

"Lots of charm and very clean. "

"Dillon was exceptional during the check in and immediately addressed our concerns. He was very informative and pleasant. The room is clean & modernly updated. "

"Great hotel, room was cute and with a nice view. 5 min walk to downtown. If we needed anything we just texted the front desk and they got us what we needed. Would stay again!"

"Ski holiday"

"Excellent stay Presidents weekend! Enjoyed the pub offering Saturday night music 🎶 Staff were extremely friendly and helpful ❄️💫"

"Great stay! Rooms were spacious. Staff and owner were great. Old world charm and great town to visit! Will definitely be back."

"This was such a cozy lodge! They provided a complimentary breakfast with plenty of pastries, bread, coffee, water, orange juice & cereal. It was super convenient that breakfast was ready by 6:30am, which was perfect timing for us to eat before hitting the slopes by 8am! This is a shared lodge, so there is a main room on the first floor with large tables & couches in front of a fireplace where you can lounge & mingle with others. Just a heads up, if you don't want to share a bathroom, make sure to reserve the "private bath" upon booking! "