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!

So much fun!! The airstream was super cool/relaxing and the animals were so adorable. Looking forward to coming back in the future!

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 great time here with our 9 month old baby. The pictures don’t do the house justice. Access to the lake for swimming and kayaking and the facilities (pools, beach, basket ball and tennis court) make this a great place for an active vacation. The house has everything you need to travel with a young child (toys, changing table, pack ‘n play and even black out shades). The towns of Athens and Coxsackie are a few minutes away and have decent food and drink options. We would love to come back!

The place is overall awesome - just don’t miss the fact there isn’t air conditioning - I didn’t notice that in the listing, and there happened to be a hot day. The hot tub isn’t quite private. One set of neighbors or folks turning down the side road can see you. However, it was very comfortable, especially on a cool evening.

Daniella and Ely are super kind and responsive. Communication was easy and she handled everything quickly. Really appreciated her support throughout the stay!

We absolutely loved our stay at this cozy, charming cabin! It’s the perfect place to unplug and unwind. Nestled in a peaceful, quiet setting, the cabin feels like a true retreat from everyday life. We especially enjoyed the screened-in porch for morning coffee and evening chats. The nearby waterfalls (a 30–40 minute walk or 10-minute drive) were a wonderful way to enjoy the area’s natural beauty. The two-person soaking tub was a highlight—so relaxing after a hike! The cabin is thoughtfully equipped with a small but functional kitchen, which made it easy to prepare simple meals. We also appreciated the high-quality linens and comfortable bed—such a nice touch that made our stay feel special. While it’s ideal for unplugging, there is Wi-Fi if you need it. There are also some cute towns nearby, full of antique shops and local charm. It was the perfect blend of nature, comfort, and low-key exploration. We’re already dreaming of our next visit!

We absolutely loved our stay at Fil & Ellie’s place, it made it the highlight of our trip. From the minute we walked in, it felt so calm. The place is beautiful with all the amenities. We enjoyed the hot tub, grill, fireplace. We’ve been to the Catskills countless times and this is the best experience due to the wonderful stay. Thank you!

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.

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 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.

What a wonderful place to celebrate our anniversary! The cabin was very homey, private and peaceful. We enjoyed the delicious coffee provided while sitting on the screen porch enjoying a spectacular view of the Berkshires. Watching the sunrise without having to get out of bed was a bonus! The cabin had everything we could have needed: kitchen items, bathroom supplies, brochures of places to visit and even a wonderful little shop to go out for breakfast and lunch less than 5 minutes away. We will definitely be returning.

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

It was a perfect price. With the ABNB it was double+. I would rather pay John more for the one night personally, than what I did. And have done twice. I have always left the place the same or better than I found it. I understand the cleaning fee, but kills single fathers like me for a 1 night trip. That being said. Walker cabin is great! Kayaks, all safety gear, fully outfitted down to toothpicks, brushes, floss, ect. You think you forgot it. It’s there. Baby monitors!

Great little cabin in the woods. This was exactly what I was looking for. Quaint, quiet, and located on a lake.

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.

We had a lovely stay at Eman's home! A beautiful peaceful Catskills retreat surrounded by nature. The home was better than the photos! Eman made us feel right at home and was so helpful. Great hospitality, she left some snacks and the kitchen was very clean and fully equipped. One of the nicest Airbnb's I have stayed in. Felt like the way it used to be back when Airbnb first started and people welcomed you as a guest, not the way it has evolved into just a business. Thanks for a wonderful stay. We will be back!

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!!!

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!