Search Holiday Homes in Stockbridge

"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."

"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."

"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 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!"

"What an amazing location. Quiet and tranquil. I would love to come back in the summer time to enjoy the waterfront activities. If you are looking for a great place to stay close to all the Berkshire's has to offer look no further. Marshal is a great communicator."

"The house was beautiful. It looked just like the pictures. The privacy and the beauty of the property made for such a serene vacation spot. The owners and property managers would respond immediately. I would definitely recommend this home. Love the Berkshires!"

"Charming and spacious historic home in the Berkshires"

"This is the 2nd time we've stayed here and loved it again. This has become our go to place to stay for our Berkshires adventures. Clean, comfortable, beautiful, private (the garden center was not open while we were there in Feb.), and great location!"

"The cabin is cozy and absolutely beautiful. We had everything we needed for a a relaxing stay in The Berkshires. Thanks for the comfort and welcoming hospitality."

"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."

"Relaxing get away. Great hot tub, table shuffleboard. 3 floors of comfort."

"Thank you, Justin, for sharing your beautiful home with my family. We had a very nice time and relaxed in the beautiful quiet surroundings. I was so excited when I saw some Norwex items as I am a consultant and also use Norwex in my home. We hope to visit again in the warmer months as it was a perfect memory for our family. Thanks again, The Short family"

"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!"

"The hosts have made this ranch house into an artsy, cozy place for families to rest and relax! Plenty of space for family hang outs and game playing, but also enough rooms for tweens or teens to get away and have alone time. Beautiful spaces throughout. We would have loved to enjoy the backyard space and screened-in porch if it hadn't been winter, but appreciated watching the snow falling while sipping coffee by the kitchen window! Close to Catamount ski area and minutes from Stockbridge shops...

"We had 3 generations of family staying here after the holidays and the home provided everything we needed - wonderful location right in town, comfortable rooms, and large living spaces to play games and catch up. The kids, parents and grandparents all had a great time!"

"We stayed with friends and family and had plenty of room. The separate game room is great! The house was as pictured and described. It is close to a few ski mountains and Great Barrington. We would happily stay at RockSpring or a different AvantStay again!"