Search Vacation Homes in Sheffield

"The house was perfect for accommodating a large group of friends for a nice, relaxing break froze reality! It gave us space for cooking meals, playing games, and lounge around. The lake was perfect for a refreshing dip! It was overall an amazing experience!"

"Lovely house and kind owner. We had a great time. The view is amazing."

"Overnight golf trip with cousins and father. Perfect accommodations not far from the copake country club. Great time"

"My family and I came in for a wedding weekend. The property was clean and spacious. We all really enjoyed"

"The property was fabulous and had lots of activities on site(basketball hoops,pickleball court and pool). Excellent location close to Great Barrington downtown which has an amazing selection of restaurants. Overall,fantastic stay!"

"The house is immaculate! One of the cleanest properties we've stayed in. The house was the perfect size for my family of 4 (2 adults, 2 teens) with room for more. The beds are comfortable, and there were plenty of linens and towels. The linens and towels are high quality, very soft. The kids had fun fishing in the pond and made good use of the kayak (they caught some bass, pickerel and sun fish). The neighborhood is nice and quiet, dirt roads, no traffic...great for taking walks. We used the...

"We thoroughly enjoyed our stay at Joe and Lisa’s stunning barn. It is rammed full of character and is very well located to explore both the Hudson Valley and the Berkshires, just over the border in MA. Joe left us to enjoy the place in peace but was always on hand to answer any questions. The kids really enjoyed taking a dip in the hot tub and making s’mores over the outdoor fire pit. We will definitely return!"

"We had a great stay while skiing for 2 days at nearby Catamount ski resort. The kitchen and house were fully stocked with all essentials. Netflix access enabled us to enjoy a family movie after a long day of skiing. Cozy house and quiet area.......nice to wake up to hear birds chirping!!"

"My family and I stayed and so enjoyed our time. The kitchen had everything we could have needed and the location was amazing to explore all neighboring towns. The beds were so comfortable and we even got out to enjoy the fire pit! Would absolutely come back again!"

"We attended our daughters wedding in Philmont. House was perfect. Views were amazing! Enjoyed morning walks and sitting outside on the deck. Very tranquil!"

"Le Soleil Suite was just as it was pictured. It was very pretty, neat and clean. Sarah provided everything that we needed for our stay and she was very responsive if we had any questions.It was so quiet and peaceful. We truly enjoyed our stay!"

"Our family had the pleasure of staying at this home during our child’s graduation from the nearby Berkshire school. It was the perfect situation for us in an idyllic setting very close to the campus. The home is over 250 years old and has been lovingly updated. The kitchen has seemingly all new appliances and gorgeous wood plank countertops with an adjacent windowed sitting area with a large hearth. The old and new are beautifully combined. Our family members spent a lot of time looking at the...

"Leah was a wonderful host to us. She provided easy-to-follow instructions for getting into the house, offered good suggestions on things to do and where to eat. Although the house was a bit larger than we needed, we chose it because of the location, the generous sized and comfortable looking (from photos) casual spaces, the kitchen and the number of bathrooms so we each had our own. This house did not disappoint! It has lots of New England charm, the beds were comfortable, as were the several...

"My wife and young daughters live in central CT, and the drive to Becket was both scenic and relatively short at around an hour and a half. The property offers great privacy in a remote wooded setting in the heart of the always beautiful Berkshires. We brought our dog along, and we all were able to relax by the fire, read our favorite books, as well as peruse interesting titles on the impressive bookshelf built into the living room wall—a book lover’s delight. We admired the openness and light...

"My husband and I had a very peaceful and relaxing long weekend at this lake house! It was very clean and has everything you need. We spent the majority of our time on the wonderful screened-in porch. The location was great and there was a little store/restaurant only a couple minutes walk up the street that was convenient and the food was really good! Overall, a great place to stay!"

"Generous facility, nicely located, accommodating host."

"We had a great time. Place is amazing. Highly recommend. We had four different families and we never felt cramped. Lovely open main room allowed us to stay connected. Bedrooms were nice and spacious, good bed options. Nice decor."

"beautifully stay for couples."

"There were 6 adults and 2 infants in our party, we were in town for our 25 year high school reunion. The house was incredible and the host went above and beyond to make sure we were well taken care of. This place is a hidden gem and deserves all of the praise."

"This home was "as advertised" - plenty of room. Nice neighborhood setting. Well stocked kitchen & nice outside area in the backyard / deck. We used it as a base camp for section hiking the appalachian trail."

"We loved our time, very cozy cabin"