A tractor up a tree! And, there's a picnic table underneath.

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Next weekend

9 Jum. I - 11 Jum. I

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16 Jum. I - 18 Jum. I

In one month

30 Jum. I - 1 Jum. II

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27 Jum. II - 29 Jum. II

Compare 86 Cottages in Winsted with updated reviews, rates, and availability.

"Great hosts who made our stay enjoyable. Very peaceful location. "

"Wonderful time..beautiful location. "

"The cottage was adorable and spotless. Minutes to Great Barrington and Butternut and close to other Berkshire ski resorts. My family of 5 was so cozy and had plenty of space. The basement bedroom does get cold, especially the floor so bring your slippers!"

Beach nearby, sun loungers, beach towels

"Jeanne was wonderful to work with and very responsive when we booked our last minute get away. Location is ideal - we brought our kayaks and very easy launching area. Would definitely not hesitate to come back to the same spot. Thanks for sharing your home with us. "

"Beautiful home with a great location in the Berkshires. We had a wonderful time!"

"The place was as described and very comfortable. We enjoyed our stay!"

"The lake and all the homes were beautiful and the house was very clean, organized, and felt like home. "

"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."

House (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

"We had a great time. The owner Bill was a great host."

"We stayed at the property for 2 nights and it was just what we had hoped. We enjoyed the lake, the fall colors and the house thoroughly. Would love to come back someday. "

"The owners freshly love this place"

"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "

SAR 1,516 total

includes taxes & fees

2 Jun - 3 Jun

"Loved our time at this cozy cottage by the lake!! Beautiful views and great antique decor in the cottage!!"

"the location and size of cottage were just what we were looking for."

"Enjoyed our stay very much. The accommodations suited our needs. Appreciated the cleanliness of the property and the ease of checking in/out."

"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."

"2nd time here so I give it excellent review."

SAR 1,041 total

includes taxes & fees

2 Jun - 3 Jun

"My family just spent a lovely week in this cottage. We came from CA and met up with my son who is an east coast college student, gathering our family to relax together in the peace of the countryside. While this cottage looks small on the outside, it actually has two spacious bedrooms, an office, a tv room, a living room, kitchen and laundry/mud room. It was the perfect size for the four of us. We had a blazing fire in the fireplace; we had all we needed to cook great meals; we felt so at home...