Cabin holiday rentals in Great Barrington

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 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!

Had a lovely weekend getaway here! Mirav’s place was clean and quiet, and everything was as described. We enjoyed the hot tub and the close proximity to Woodstock; it’s less than a 10 minute drive, so easily accessible for good food and cute shops. Would definitely stay again!

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.

This my third time back to Ellen’s cabin. It’s great place for a weekend in the Catskills. The property is beautiful and very private. The area surrounding the cabin is equally as beautiful. I plan to come back for many years to come.

Upon arrival we were greeted by an owl! This place is magical and has absolutely gorgeous surroundings. Definitely rustic, but as expected 🙂

We loved William’s place and he was a fantastic host. Check in was easy and super flexible. The bed is EXTREMELY comfortable and the accommodations are delightful. Would definitely stay here again!

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

We loved our stay at this unique dome house! Our son was graduating from Kent School and it really made our last time in Kent very special! The craftsmanship is incredible and it is decorated with a lot of attention to detail. The kitchen is well stocked and there are plenty of beds for people to stay for a large family. It’s also very private and close to Kent Falls state park which is beautiful and fun to see. Ana was very responsive and a great host! I highly recommend this property!

It was our third stay here and it continues to be one of our favorite places. Surrounded by woods and yet a close walk to town. Mary Anne is a great host and is quick to respond. Thank you for another wonderful stay!

This is the perfect cabin retreat. Beautiful property with incredible back porch views, stunning fireplace, creekside access, and gobbling turkeys in the distance. It was just what I was looking for to celebrate a birthday with friends. Secluded enough to feel private but close enough to a charming town for drinks and coffee. Jim was also super communicative and made it easy to settle in—he even gave me a heads up about the weather that weekend to make sure we were packed appropriately. I was considering a couple of places, and I’m so happy I chose this one. Highly recommend a visit. P.S. The heated floors are a really nice touch.

Six adult members of our family gathered to celebrate a milestone birthday, and we had a wonderful time. Maria contacted us the week before, so we knew how to get in and all other necessary details. We loved the spacious living room and dining area, the large windows looking out at the woods all around, the cleanliness of the rooms and linens, the games provided, and the well equipped kitchen. We were very comfortable and happy to be there. The house was great and Maria was a top-notch host.

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!

Wonderful restful getaway. Everything you need clean, comfortable, gorgeous view, beautiful cross breeze.

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!

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. :-)

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.

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!!!