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2 Jum. I - 4 Jum. I

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9 Jum. I - 11 Jum. I

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23 Jum. I - 25 Jum. I

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20 Jum. II - 22 Jum. II

Compare 89 Cottages in Chester with updated reviews, rates, and availability.

"Wonderful getaway, lovely hosts, great location, overall a fabulous place to relax and recharge. "

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

"Stayed with family for a wedding nearby and had a great experience. Nice house, clean and comfortable and as advertised. Very comfortable bed. Remote location so it’s quiet and peaceful, and short walk to lake. Host was very helpful and quick to respond. Would stay again!"

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

"Excellent property: would have liked to stay longer. "

"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."

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

"It was a very quiet unique place to stay! You get a beautiful place with a lot of history and Good feel! I sent a picture to my dad and he Remembered using those same desks when he was a kid. Very nice weekend."

Fridge, microwave, stovetop, coffee/tea maker

"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."

"This house was more than we could ask for it’s right on the water and has everything you could possibly forget handy! A all around, great place to enjoy nature and spend time with family and friends. Super straightforward didn’t need to ask the host any questions Will be booking here again! "

"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."

"Stayed for 3 nights over Presidents Day weekend, and we loved the spot! Recently refreshed with a new kitchen, floors and fixtures, it’s still felt warm and inviting. The electric fire / heater in the living room was well used, and we cooked our meals with the new appliances and well equipped kitchen. Proximity to Great Barrington, Stockbridge, Lenox, Lee, and all of the outdoor adventures (and shopping/restaurants) worked out perfectly, even given the snowy/ice weather. Plenty of space for the...

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

SAR 1,054 total

includes taxes & fees

30 Apr - 1 May

"Beautiful lake house and ideal for our group of 4 women celebrating our 45th high school reunion. Beautiful lake view and Love that Ozzie’s is just a few miles away. "

"Very nice house. Owners very helpful."

"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...