Photo by Elizabeth Massa Peroulakis

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Compare 23 Cabin Rentals in Chester with updated reviews, rates, and availability.

"The Cabin Had All The Amenities You Would Need and With A Quiet and Serene Area. For Me It Was Relaxing Stay!"

Otis Vacation Rental | 3BR | 2BA | 1,200 Sq Ft | Stairs to Access

"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."

Mill River Vacation Rental | 2BR | 1BA | Stairs Required | 1,100 Sq Ft

"The Mill River Cabin is the perfect location for a vacation focused on relaxation and communing with nature! We recently enjoyed a beautiful fall week at this property. Highlights included time spent on the deck overlooking the Konkapot River, evening campfires, hiking the large number/variety of trails very nearby, Hancock Shaker Village and the Norman Rockwell Museum. This rustic cabin has everything you need to make for an enjoyable stay. It's a good idea to bring your food and other...

Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required

"We had a wonderful stay. The cabin was clean and comfortable! "

"Wonderful accommodation."

Tolland Vacation Rental | 2BR | 2BA | 1,200 Sq Ft | Stairs Required

"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...

"My partner and I really enjoyed our relaxing stay at this quaint cottage. It was clean, comfortable, and tucked away in a very quiet area. It was easy to get to restaurants and theaters in Pittsfield / Lenox / Stockbridge. The hot tub was also a great way to spend a cozy fall afternoon!"

"Great"

Spacious interior with tall ceilings and lots of light.

"We had such a wonderful long weekend away that this home. Everything was exactly as pictured. Home was clean and so welcoming. Location was perfect for all that Great Barrington has to offer. The wraparound deck and fireplace made it all the more special. Communication was excellent and we got quick replies to any questions that came up. I would definitely recommend staying here and would happily return."

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

Becket Vacation Rental | 2BR | 1BA | 1,100 Sq Ft | Stairs Required to Enter

"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!"

East Otis Vacation Rental | 2BR | 1BA | 720 Sq Ft | 2 Steps for Entry

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

Goshen Vacation Rental | 2BR | 1BA | 725 Sq Ft | Stairs Required for Access

"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...

"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."

Westhampton Vacation Rental | 3BR | 1.5BA | Stairs Required | 1,705 Sq Ft

"Loved our stay. "

"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! It is conveniently located for Tanglewood and the Rockwell museum, quiet and secluded. The cabin and grounds show much care and attention by thoughtful owners. "

Stockbridge Vacation Rental | 2BR | 2BA | 700 Sq Ft | Stairs Required

"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! "

"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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Chester Vacation Rental | 2BR | 1BA | 2,000 Sq Ft | Stairs Required

"The stay at the property was enjoyable. The space was large, spacious and very clean. Two people were able to stay quite comfortably."

"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "

AED 821 total

includes taxes & fees

30 Dec - 31 Dec

"My family and I really enjoyed our stay at the lake. My kids enjoyed playing outside in the snow. We had such a quality family time playing board games, watching movies and drinking hot cocoa. Justin was such a great host and really helpful when needed. We’re definitely coming back!"