Search Cottages in Pittsfield

"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"

"I adored my stay at The Stone School. Rich and Cheryl were terrific hosts who had great suggestions for food and things to do. And the whole experience was easy to navigate. Excellent marks for cleanliness, comfort, ease of parking, quiet & solitude, quaintness, local pleasures. I found it perfect for myself and it would also be ideal for a couple (or perhaps a couple with one or two young children.) The bathroom is on the first floor with a modern sink and vanity; everything looks brand...

"I have nothing but great things to say about our stay! Our hosts were great and very welcoming. The property was beautiful and our cottage as well. We will most definitely be back! Thank you!"

"A very nice stay. Communication with the host was great. We kept bothering her with questions and she responded quickly. The place is really beautiful. We lit a fire each night and played some of the provided games and watched Netflix. It's an easy drive to Great Barrington to get groceries at the Berkshire coop. We also took advantage of our surroundings and hikes on the AT a little each day. Next time we'll use the host's canoe to explore Lake Buel. The only minor complaint I would have is...

"Very clean property with nice amenities near beautiful lake. Beds were comfortable owner very helpful with anything you might need"

"Nestled among luxe lakefront properties, this tidy cabin was perfectly suited to relaxing in kayaks and family dinners. Near Great Barrington and lovely hikes. Exceeded all expectations for a last minute getaway."

"Imagine walking into a bright, open space surrounded by comfy furniture, a virtual library of interesting books, a complete kitchen, and best of all, wonderful, thoughtful hosts. If Kinderhook (or the Hudson Valley Region in general) is your destination, don't hesitate to book this private, airy oasis. Everything you want and need is here if your goal is a relaxing, comfortable stay in the beautiful Mid-Hudson Valley."

"the property was very well maintain, the host put alot of very personal and special touches inside the house.i have stayed in alot of houses over the years, but this one the host made you feel right at home."

"Beautiful home on water. Perfect place to have family gatherings! Looking forward to another visit. Best area for pizza, too! ( Kay’s)"

"Second time staying at the property. Comfortable, low key cabin. Access to private beach a big plus. Near Lenox, Stockbridge and Tanglewood."

"I’ve been visiting the Berkshires for decades and never stayed at a place with such an amazing view of Lake Buel! Sunrise right from my bed. The house was stocked with everything that was needed for an amazing weekend. Wonderful place to stay!"

"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...

"Quaint cabin tucked away in the Berkshires. For those vacationing with a pet, be aware that on Labor Day weekend this neighborhood puts on a fireworks show right by this house. Also, there really is not any yard, just a small patio. Lots of great hiking in the area."

"A sanctuary for writers and astronomers! Exquisite cottage and surroundings. Short hop to all that goes on in the Berkshires. You won't want to leave!"

"It was perfect for me and my close friends. We enjoyed the lake each day and all remarked that the beds were very comfortable. Wish we could have stayed longer."

"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."

"Staff were so attentive, even at the late hour we checked in (10pm) the place had everything you need. Amazing views and amenities. Loved it"

"We loved our time, very cozy cabin"