Cabin holiday rentals in The Berkshires

5 out of 5 stars. Used this as an opportunity to get away with my pregnant wife, and we were not disappointed. In fact, we wished that we had booked at least another night or two! The pictures for the listing were great, but we felt the cabin looked even better in person. It was clean, homey, and had everything you needed for a usable kitchen. Lasse’s detailed amenities listing and clear directions in the cabin (like how to properly use the hot tub) far exceeded our expectations. I don’t have one negative thing to say. We are already planning to book for next summer!

Perfect mountain getaway for a great price without being tooooooooo up in the mountains.

Beautiful house and interior. The house was clean and well prepared. The basement is an entertainment hub. The weekend we visited was cold but the fireplace inside the house and fire pit outside made the weekend enjoyable and fun. Very pet friendly. Our dog had a great time exploring the woods while we in the hot tub. Amazing place to have a chill weekend with friends and loved ones.

Very cute and convenient stay. We had everything we needed and more. We would recommend this place to anyone desiring to get away and enjoy the Catskills.

We had an amazing getaway at the cabin! Great and beautiful place to disconnect and unwind! We will definitely want to come back in the fall. Highly recommend!!

The cabin was great! Just what our group needed. Very clean and in a nice private location.

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!

A wonderfully relaxing place to stay. The hot tub and sauna are wonderful, as is the bedroom with the view of the mountains. We plan to come back soon.

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.

A charming home, convenient to Woodstock and Phoenicia. We enjoyed the quiet, wooded setting (from inside you can hardly tell there are neighbors) and the cabin-like feel. Everything was very clean, Nickie's instructions to access the home were clear, and we very much appreciated that the place was dog friendly and that the main bedroom and the bathroom are on the main floor. The deck also has a gate, so had it not been so rainy, our dog could have hung out with us outside.

Such a cute spot! We only spent one night but could have spent many more. The home itself is adorable and had lots of thoughtful touches. The beds were super comfy! They had some board games we ended up playing late into the night. Highly recommended!

The house was beautiful and had everything we needed, even instructions in case of bad weather. We felt so comfortable and relaxed during our stay. We would absolutely recommend staying here for a weekend getaway! Thanks so much to Kelsey for everything!

We had such a lovely time! The property is beautiful, and our dogs really enjoyed the peace and quiet and getting to spend time out in nature. The place is well-furnished and comes with all the amenities you could need, including cooking utensils, tea and coffee, condiments, bug spray, wood for the fire pit, games, and bowls for the dogs. Jeff and Sharon were very responsive and provided lots of helpful information for our trip.

This cottage was Magical. Reminds me of a cottage out of a storybook. Incredibly peaceful and quiet tucked in the woods. The cottage itself was so lovely and Lisa thought of everything. Well stocked with kitchen, bathroom supplies. I loved the games and record player with tons of records. The cottage is super clean and Lisa was an incredible host. I needed to contact her and she was very responsive and thoughtful. I would highly recommend and will be back in the fall ✌🏻

We booked our trip day of to take a long weekend out of the city and I could not stress how perfect it was! We have two kids under 7 and the property provided so much space and safety to run around. On the days it rained, we enjoyed the patio area (with a huge tv). The creek in the back lended us hours of entertainment for our kids and finding the “surprise waterfall” to the left was very exciting! Brianna was available to answer any question we had within minutes. Although we could have stayed at the property the entire time, we tried out some places from the suggested list Brianna left. June Farms was great and the Towne Tavern had amazing wings. We’re excited to come back and sit on the patio during winter months! (They have a heater too!) 10/10 experience

We had an amazing time! Danielle and Ely were very accommodating and went out of their way to make our stay special. They answered all our questions, helped us book a table at Matilda, and even surprised us with complimentary wine. It was so thoughtful!

Spent a beautiful weekend at this cottage. The property is beautiful. Lovely to hear the birds and view the gardens. It rained most of our trip but we didn’t mind because it was so restorative to hunker down and relax here. Well stocked kitchen. Nice bedding. Close to Brattleboro and easy access to hiking/farms etc. Kathleen was the perfect amount available. We’re sorry we didn’t get to meet you in person!

We really enjoyed our stay (even with the rainy weather) and had a great time walking the property or visiting the nearby hiking trails suggested. Would definitely recommend!

This place is beautiful. Host is very responsive and helpful. I will say the road to get up to the house is very steep so be prepared. Otherwise all was great and would highly recommend staying here.

Incredible air bnb experience. Hosts were extremely hospitable (along with their adorable pups)! Place was cozy, remote, clean, and decorated beautifully. Will definitely be staying here again. They also responded to each question within minutes and even reached out to us when we forgot a couple of things and offered to ship it to us if we weren’t in the area. 10/10 hosts and beyond!

What more could you want? This quaint cabin situated in the woods offers privacy, unique architecture, comfort, and peace. It’s equipped with everything you could possibly need, and the hosts were truly some of the most responsive and kind people I have ever interacted with. They truly went above and beyond for us. We stayed with a toddler and two dogs, and they all loved the property and the cabin. We will most definitely be back!

What a beautiful place and warming hosts! I had an amazing time at the home and the town was filled with wonderful people, food and relaxing atmosphere. I will definitely be back 🙏

Wonderful stay in a lovely house with unique welcoming charm in a great location. The attention to detail made us feel at home. We loved the screened-in room. It felt like sitting in the woods without the mosquitos. Bruce was a super responsive host. Highly recommended.

We LOVED our family’s stay at Mike’s place—well equipped for young kids, every amenity you could need, and the most spectacular location in the middle of the woods. The area is gorgeous and secluded—but also an easy drive to Great Barrington and its lively Main Street.