Search Holiday Homes in The Berkshires

"We loved our two night stay in the forest :) The house was super clean, well appointed, quiet and relaxing. We didn't have great weather so didn't get to take advantage of the perfect spot on the lake or any of the kayaks or boats, but the location was a great jumping off point for visiting the various Berkshires towns."

"Generous facility, nicely located, accommodating host."

"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!"

"Very clean, tastefully decorated place perfect for our weekend getaway for two. Enjoyed the reading nooks and kitchen amenities, comfortable bed and peacefulness of this carriage house!"

"Very clean property. Close to trails. Host thought of everything we might have needed. Quiet neighborhood. Fenced in yard made things much easier with our dog. She even provided dog bowls, towels, rug and a treat!"

"My daughters and I really enjoyed our stay at Dancing Horse Lodge and would love to stay again! It's a great location - close to great stores and restaurants, so even though it rained for most of our stay there was plenty to still do. And then our time on property was relaxing and had everything we needed! Definitely enjoyed the gas fireplace, and our accommodations were very comfortable! Hoping to book another trip here late summer/early Fall."

"We have a lovely stay, house is super clean and has all you need to relax and enjoy the space. I loved the fact we could take our small dog with us to make it a lovely family’s vacation. The house is central to everything and all towns in the Berkshires which we appreciated so much. We will return and would recommend to other highly also."

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

"Be aware they will not proactively provide you with a local host name or contact info. It was very difficult to get Vacasa support to help me get this info to resolve wifi issue - like hours long to get them to just give me the property managers info and even then, they wouldn't give it to me, just had them contact me. Otherwise, amazing pool and great location. Outdated indoors but clean to the extent that it could be. Utensils were dirty and tons of flies in the house upon arrival - like 50...

"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."

"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!"

"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."

"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!"

"Nice cozy cabin close to Otis Ridge Ski mountain - house was clean, comfortable, had everything we needed."

"Perfectly location for Lenox, Stockbridge, and other local towns. House was just as described and comfortable for a family of 5. Property contact was proactive, reaching out to make sure we were settled in. Pacman and air hockey games were a big hit! We would book again."

"Charming and spacious historic home in the Berkshires"

"Kimberly was a great host. Very attentive. The house is in a great location on a fantastic property, right on the lakefront. Wonderful views, cozy fireplaces great kitchen, and acess to a 2-car garage."

"This was our first VRBO experience, and we are hooked. We had a wedding in Pittsfield with events over three days, so we decided to try this lakeside retreat, and it was a treat! The Berkshires in the fall are absolutely beautiful and Hinsdale is a pretty little town. Ozzie's is definitely worth the trip for breakfast. The lake is lovely and we were looking forward to kayaking and fishing. Unfortunately the weather was not on our side, but we still got one fish! Mary is a wonderful host who is...

"Clean, well appointed, and a wonderful backyard space. Great experience and would stay here again."

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

"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."

"We loved our two night stay in the forest :) The house was super clean, well appointed, quiet and relaxing. We didn't have great weather so didn't get to take advantage of the perfect spot on the lake or any of the kayaks or boats, but the location was a great jumping off point for visiting the various Berkshires towns."