Search Vacation Homes in Chatham

"We rented for the winter to use on the weekends. Sabrina was very responsive and thoughtful throughout. The house is incredibly well stocked and thoughtfully organized. Two seating areas downstairs made it easy for our family of four to spread out, even when we had guests. Kitchen is well laid out, mattresses are very comfortable, and the surrounding area is quiet. We would definitely go back."

"Sarah is a great host and gave helpful suggestions for things to do in the area including a couple of amazing hikes. The house is a charming farmhouse fully restored to its original glory. We built a couple of cozy fires - both inside and out - perfect getaway."

"Very,very clean nice home lots of comforts of home. Would definitely stay here again. Great area and the poeple were very nice. Couldn't have better host ,they were awesome!!"

"We had a wonderful time celebrating Birthdays with friends at this newly renovated, warm and welcoming home. Close to downtown Great Barrington, restaurants and shopping. The house was immaculate and well decorated. I highly recommend this beautiful home."

"Wonderful old house with character, great beds, great fireplace, good kitchen (missing only a 9x13 baking dish - but we made lasagna in a round baking dish)! We walked by the river in Great Barrington, visited the old courthouse/library/gallery in Lenox and walked Lenox in the rain then warmed up at delicious cafe Shots. It was just a long weekend, but we plan to return so we can explore trails on property and visit more local sights. Appreciate the welcome book/visitors guide provided by...

"Very roomy and charming. We didn’t get to stay long as we were in town for an event - we hope to be back. Location allows for walking to anywhere in town. Jeff is accommodating and responsive, ample parking. No issues."

"Wonderful stay, everything was as advertised. My friends and I chose the place for the home theater and it was just what we wanted. Communication from the host was great and the place was comfortable, spacious, and clean."

"Excellent stay - townhouse was very clean and smartly outfitted to anticipate the needs of guests. Sweet extras (granola bars, bottled water, toiletries) that we didn’t expect. An easy walk into town for meals. Appreciated the ease of check in/out. Thanks!"

"The property was clean, well taken care of, and really lovely. It was also in an incredibly picturesque setting and the hosts were an absolute delight to work with. I can't say enough good things about the property! Book it today!"

"We had a very relaxing weekend at this scenic house. Directions were very clear and the guide book they provided was very thorough. Dan was attentive and responsive to the few questions we did have. Would definitely come back!"

"We stayed here between Christmas and New Years visiting family in the area, and we had a lovely time. The house was spotless and had everything we needed, from abundant towels down to a rubber band in the kitchen drawer. Beds were comfy. The owner, Julie, was a friendly and gracious host, and even left us gifts and homemade holiday sweets, making our stay feel very festive. We’ll definitely be back next time we’re in the Berkshires!"

"2nd time we stayed hear. Great place! We hope to go back again. It is near Hudson. NY where our family members were born and raised."

"Charming and spacious historic home in the Berkshires"

"We had an excellent time, and even though the weather didn't cooperate with us to enjoy many outdoor activities, Summer Wind made up for it with a roomy and comfortable place to hang out with old friends. We will definitely keep Summer Wind on the list for future Geekends <3"

"We came to visit our daughter who is in college in the area and loved the location of the house! There was plenty of room, house was clean and had everything we needed. The host, Stephen, was wonderful to work with, great communication and made sure we were happy and had what we needed! He also gave recommendations for places to eat nearby! Very happy with this property and and our stay!!!!"

"The property was quiet and clean."

"We had a wonderful family get together in this lovely, cozy, well kept home. Gorgeous view of the lake. Enjoyed kayaking and row boating. Game room was great. Would definitely come back again."

"Impeccable home beautifully decorated. Cozy fireplace and great communication with host we’ll definitely be back!"

"The house was exactly as advertised, comfortable, and with great location. We enjoyed a great weekend of skiing at both Catamount and Butternut, and the kids enjoyed their first ski lessons. We even got a few inches of snow to go with it. Howard was an excellent host, very easy to communicate and always reachable. We will be back for sure!"

"Generous facility, nicely located, accommodating host."

"We've stayed in a lot of home rentals - and across the board - this was the best place ever. The home was clean, nicely decorated and super comfortable. The hosts were easy to get a hold of and incredibly welcoming, leaving us with a generous basket of local treats. We loved the peaceful outdoor space and roamed all 40 acres. The pond was beautiful and if it had only been warmer we'd have jumped in the rowboat. We will be back for sure. A++ Thank you, Anna!"

"Very nice spot quiet "

"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"