Cabin holiday rentals in Great Barrington

What a treat to stay at McCaela's magical, cozy, home! Everything – from the surroundings, to the furnishings, to the amenities – were just perfect. Entry into the house was no problem, and inside we found a delightfully thoughtful and intentional home that was extremely comfortable and spotlessly clean. Just as key, the bed in the primary bedroom was supremely comfortable! We had no reason to ask any questions, and we had no issues at all; still, McCaela reached out to make sure we were settled and to see if we needed anything. We SO appreciated her generosity, kindness, and insight into (and commitment to) the local community. It's clear that a great deal of thought and care has gone into this house, and we would stay there again in a heartbeat. The location is perfect – off the beaten path and extremely private, yet close to everything we wanted in the Berkshires. I highly recommend staying here, ideally for longer than the two nights we did. We can't wait to return!

Amazing spot, great weekend, would happily come back in the future :)

Amazing stay in the forest! Cozy, peaceful, and super romantic. Perfect place to relax, disconnect, and enjoy nature. Thank you for the unforgettable experience!

Our stay in the Airstream was amazing! The cabin is beautifully done-up, with lots of thoughtful details like fresh milk and eggs from the farm. The hottub made our nights extra-relaxing, and having the farm to walk around and meet all the animals was such a nice way to spend a morning. Bring eyemasks though - the curtains are quite sheer!

Michelle's Hilltop Cabin in Chesterfield, MA, is a wonderful place. Nestled in the Berkshire woods, but close to the road, and not far from civilization, this place has all the best western Massachusetts has to offer. 11 miles (15 minutes) to Snow Farm (Williamsburg) 17 miles (28 minutes) to downtown Northampton 23 miles (36 minutes) to UMass Amherst 31 miles (44 minutes) to Mass MOCA (North Adams) 32 miles (51 minutes) to Tanglewood (Lenox) The Hilltop Cabin is best for 2-3 people, but Michelle has several other rentals at the same address. See if she has openings to suit your party on your dates. You won't be disappointed!

My partner and I absolutely loved our stay at this cabin. The views from the home and the surrounding area were amazing and we found ourselves just slowing down a lot on our drive there to take it all in. Our favorite parts were the hot tub which was so relaxing especially with the backdrop of nature behind us and the amazing kitchen where we cooked all of our meals each day. Most things were around 20 minutes out so it was a very stay at home stay so we really appreciated the effort they made at making the home the main attraction. The host was very communicate and helped solve a minor issue we had right away which was a great experience. Our least favorite part was having to leave! Overall we look forward to coming back again in the future to such a cozy home.

We had a wonderful stay at Marta's house. Everything was spotless, well cared for and thoughtful. The check in process was so simple and the house rules were easy to follow. The record collection was such a nice touch, especially on a rainy Saturday afternoon and the basement with a full media setup and games was perfect for a Saturday night in. The beds were comfortable, plenty of towels and amenities and the hot tub was great as well! The location was also great! Nothing bad to say about this amazing little spot :-)

We had an amazing time at Ruth’s home and we loved the cabin feel. Between the hot tub, lake, and lawn games our time went by so quickly. The home was very clean and had all the essentials. We will definitely be back again!

Fil & Ellie’s place was the perfect stay for our getaway. Their home is amazing. We were very impressed by the amenities, the cleanliness and attention to detail. This place has everything you’ll need for a great stay. The hosts were also very helpful in answering our questions and assisting us with check-in. I would highly recommend staying here if you have the chance.

Beautiful little cabin, peacefully in the woods. Great, friendly, and responsive hosts. Perfect location to relax, walk around, find closeby hikes and hidden gems, including some great breakfast spots. 10/10 would recommend.

We had a lovely stay at Betsy’s cabin for a long weekend. It’s a perfect location making it easy to explore the Berkshires. We loved the cabin atmosphere with modern day touches. Betsy was a fabulous host! We will definitely be back.

Bob is an absolutely amazing host and is incredibly communicative - he was always looking to ensure that we were enjoying our stay and that any issues were remedied as quickly as possible. The home was exactly as described: immaculately clean, very comfortable beds, and full of thoughtful touches that made us feel right at home. It was raining quite a bit during our stay, but the amazing view from Bob’s cabin was more than enough to make up for the bad weather. We wouldn’t hesitate to stay here again and highly recommend this place to anyone visiting the area!

John was a very welcoming and kind host :) He gave us a warm introduction when we arrive and great recommendations The house is immaculately clean, beautiful, comfy and overall very comfy All you can think you need is in the house Some deers came to say hi too! It was wonderful We will be back again soon THANK YOU

Loved this cabin ! 10/10 recommend and will book again!

This is one of my favorite Airbnb’s. Charming, cozy, and peaceful—truly a gem. Jolene goes above and beyond as a host. I highly recommend this guest house if you’re looking for an enchanting getaway.

Rachel’s cabin is rustic and charming - the location is beautiful. Rachel is very friendly. I enjoyed my stay.

Sahar's listing was exactly what i was looking for to get away for a weekend. I stayed at the Sol cabin which was located right next to the start of the hiking trail. The cabin itself is clean and the kitchen has everything you need to make a simple meal. The property is very private and I really enjoyed my stay. Would recommend to family and friends.

Really enjoyed our stay! Was perfect for our family to stay all in one place. Darin responded in a timely manner and was very helpful. Pool table was a great addition! Loved the location, it was beautiful & peaceful. We were disappointed we didn't see any bears :0) LOL

We loved our stay in Jeremy and Danielle’s cabin. It was warm and cozy and rustic yet modern. The place was in pristine condition, and we felt immediately at home upon entering. We will definitely rent it again the next time we are in the area. :-)

Great for a weekend away with my friends and I!!! Looks exactly like the pictures and was listed for an AMAZING price for everything that we got! Would totally come back and could not recommend enough!!!

Amazing cabin!! My third visit. Was there with friends for fishing and I love the cabin so much that I booked my anniversary weekend and my wife is also in love with the property. Relaxing Birding Fishing Kayaking Fire pit Romantic This place has it all! Book it now! You won’t regret it!

We had a wonderful stay at Marco's place. The cabin was very cozy in the woods, but the towns of Hudson and skiing at Catamount were both a 15-20 min drive away. We loved doing puzzles by the fire and cooking in the kitchen, and my daughters loved the children's toys that were kept downstairs. It was the perfect weekend retreat!

Pictures don’t do it justice! The place is super adorable and relaxing. Great views and vibes. Personal touches that make you feel like you’re visiting a friends home instead of an Airbnb. Highly recommend!

Clean and cozy. Terrific Host!