Photo by Elizabeth Massa Peroulakis

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Compare 27 Cabin Rentals in Chester with updated reviews, rates, and availability.

"We had a great time here and the hosts were friendly and accommodating of our request for a later checkout. Our only complaint is the 325 cleaning fee, which is excessive given how much cleaning guests are asked to do (and given that one of the bathrooms was not even perfectly clean upon arrival). We would otherwise happily consider a future stay."

"Very enjoyable stay, highly recommended."

"We had a great time in the cottage. It was perfectly cozy for our family of 6. The cottage has everything you need to have fun on a cold winter night. We especially enjoyed the hot tub and board games! Thanks for a lovely stay - we will come back in the summer!"

"The hosts were extremely responsive and helpful, providing us with hiking ideas, questions regarding the house and suggesting best shopping spots for incidentals. The living room was cozy, seating five comfortably. The kitchen was well stocked so cooking a Thanksgiving meal was a pleasure. We thoroughly enjoyed ourselves."

"I want to preface my review by stating we had a wonderful time. We needed a getaway to unplug and relax and we were able to do just that. The area was beautiful, nature-plenty, quiet, secluded. There were a few unexpected glitches but nothing that we couldn't improvise around. Having said that, the listing said queen size beds, but they were only full, so my husband and I stayed in separate rooms which was sad . We also felt the people that prepped the home for our stay, must have ran short of...

"Wow! It's a gorgeous, artsy (in the best way),very warm and inviting cabin in the woods. So much privacy AND a stream/river right outside your door.For nature lovers, those seeking privacy in a quaint, laid back section of the Berks."

"Beautiful lake, traditional charming cottage- great get-away"

"Lovely cottage. Very clean. Everything we needed. We had a great time!"

"Great"

2 bedrooms, iron/ironing board, internet, bed sheets

"This Pet-Friendly Cabin was very cozy. It is in a woodland neighbor of cabins, but it feels very secluded. Nobody was at the one cabin that we could see. The weather was cool while we were there, so we enjoyed a campfire outside and one in the indoor fireplace. The cabin was decorated by someone like my grandma who was obsessed with bears and apples. The cabin is a short stroll from a lake with a beach. Although our overall experience was good, there are few negatives. First, there are no...

"This A-frame cabin was the perfect location for some Berkshire R&R. Close to so many of western MA's greatest attractions, we had a great time visiting Tanglewood and museums, and touring local towns and restaurants. The property was clean, as described, and very comfortable. Communicating with our hosts was very simple. We will be happy to return!"

"Great location, comfortable, beautiful setting and nice porch! "

"A wonderful cabin with all the amenities you will need. Clean, beautifully decorated, and so much room. Highly recommend! Will be back for sure. "

"We love this place as the lake is extremely quiet and clean. The house has a great living room with lots of charm and plenty of bathroom and bedroom space. I wish I had something bad to say because we could keep it to ourselves, but I do not."

"Loved our stay. "

"Needed some time away back in New England and this was the perfect spot. Very comfortable, quiet and clean. Within a mixed vacation home residential area on a lake it was very quiet in the fall, but likely more bustling in the summer, but it is in a lake community. Nice, well built log cabin, clean and maintained. The owner communicated everything well and is easy to contact. The cabin are very close to Hinsdale and Dalton which has more amenities. Many state parks, woods and conservation lands...

"Trip was great. House was comfortable and pretty. Great for a reading getaway. Very relaxing."

"If you’re going to events at Tanglewood, this is a prime location. We added on an extra concert because of the easy 6 minute drive. This little lake cabin was quaint and cozy. The outdoor shower was superb. Would definitely stay here again! "

"Wonderful accommodation."

"This cabin is very well-maintained with all the amenities you could ask for... especially no cable TV, and the owner David is responsive and pleasant! It is the perfect place to unplug, unwind and reconnect with life, nature and whoever you're traveling with. The house is an easy 30 minutes to Tanglewood and 20 minutes to Great Barrington so there is plenty to see and do without feeling like always being in the car. We got takeout from a delicious Thai restaurant (Siam Square) in Great...

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"Very comfortable property in a lovely setting "

"3 day holiday getaway, my husband and our 2 pups. A hike in nearby trails in the woods, enjoyed Lee downtown eateries and shops. Beautiful winter wonderland in the Berkshires. The guest rental was perfect!!! Warm, spacious, comfortable, perfect location. "

"Thank you for sharing your wonderful home! It had everything we needed including a quiet, peaceful, private, beautiful location, comfortable bed, great books!!, and a well equipped kitchen. We are very grateful you had availability for our Thanksgiving visit with family. Thank you!!"