Guest house holiday rentals in Berkshire County

We were in Lenox to attend a reunion for the Lenox School for Boys ( Grad “66” ). The cabin was perfect for our needs especially because we could have our dog with us. Most of our time was spent with activities scheduled for the reunion so we didn’t really get to enjoy the peaceful atmosphere surrounding the cabin. There will be another reunion in 2026 so we will be looking forward to another stay at the Luv Shack. Thanks for sharing your abode. Pete & Becky Davis Mechanicsburg PA

This was our sixth visit to Maple Hill Farms — we just can’t get enough of it! Philip truly the best host, and his home is pure magic. We’re so grateful to have met him and to experience his incredible hospitality and a property filled with the most amazing creatures.

Happy to be back at this lovely Airbnb! Clean and cozy as always with an extremely comfortable bed and sweet tub. Rochelle was instantly responsive when I reached out with an issue with the door lock when entering (due only to the very cold day). She gave us an easy tip and we were in in less than two minutes. This is a great place to stay.

This was our first trip to the Berkshires and it couldn’t have been more perfect. Tracey and Sean really host a home away from home that’s probably as close to feeling like a local as you’re going to get in this magical region. We’ll be back!

Nice, private, large room. We loved the real flame of the franklin stove. Little mini-kitchen. Nice duvet on good queen-size bed. Very private, separate building. There is a swimming pool, but that's summer-months only. We liked that it was just a 5 minute drive to Williamstown and the Clark. Not really enough hot water for two showers in a row, but other than that, great. Well appointed, with shampoo, Q-Tips, salt, sugar, etc.

Fantastic stay with wonderful hosts! Wednesday and Jim were so kind and welcoming- had a great time in the midst of a fairly sizable winter storm. Would stay again!

I really enjoyed my stay at Galina's cabin and would definitely stay again. The cabin itself is well laid out and decorated, and was very clean when I arrived. The location was perfect for what I wanted.

Mary’s space was calm, quiet, and perfect for a quick weekend trip to the Berkshires. She was very responsive when I asked questions, which I really appreciate. I will definitely consider staying here again in the future!

We loved our stay at the barn! It was the perfect location for a weekend family ski trip for our family of 5. The barn has a cool old/rustic feel, but with all the modern touches to keep it comfy and cozy. We loved the decor and how it highlighted their outdoor and fly fishing passions. Family friendly games were available for après ski along with easy TV access. For the local area, Catamount was a quick <10 minute drive. Kimberly gave great dining recommendations in the area - Hy's Fried and Agaves were both hits! I wish we had more time to explore downtown Great Barrington. Can't wait to stay again!

Briee and Jared are super friendly, approachable, and in general the most wonderful hosts we've ever had. Briee is very proactive and communicative. She sent emails to check in and very thoughtfully provided us with great amenities and support. The place is very quiet and the house is so very beautiful. Besides the clean furniture and rooms, the house is decorated with cards and equipped with books of poetry and literature, as well as local recommendation pamphlets. My parents and I spent three weeks here, and we are grateful that we had this meaningful experience at Briee's.

This was our 2nd stay at Christian's place. Every was great once again. Peaceful, beautiful with lots of things to do in the area. Thanks Christian, we will be back again!

Wonderful place to stay. The house is comfortable and well equipped.Geoff and Cindy were attentive and helpful. The location is great -- lovely bucolic scenes but close to Lenox.

Mary was an incredible host, and her home was beautiful. The scenery was stunning. I loved looking out on the gorgeous fall foliage each morning in bed while having coffee. Mary provided everything that we needed and more. She made sure that they were all the toiletries that we might need, as well as snacks, coffee, tea and oatmeal for breakfast. She even left us some Prosecco and chocolates to celebrate our anniversary. We will definitely return!

This is a lovely cottage in a beautiful location amidst older homes near the center of Lenox. The location is very convenient for outdoor and cultural activities in the area. The fireplace made it very cozy in the cold and inclement weather. It was perfect for a getaway with our two adult children. I would love to return in the spring or summer to see the landscaping around the cottage in bloom and enjoy the local activities in warm weather.

The Blue Jay Cottage was the perfect place for a quiet getaway. My best friend and I went for a girls weekend and were very happy with our decision. It was absolutely adorable inside and the fireplace was amazing. We came during a winter storm and the hosts were very kind and accommodating with shoveling, salting, and even offered us alternative parking. Perfect location to visit all the must see Berkshire towns. Overall great hosts and a wonderful place to stay.

I absolutely loved the stay. The location was nice and peaceful with close proximity to local restaurants and shopping. The home was very well kept and had the amenities needed for a full months stay.

Abigail and Paulo’s attention, responsiveness and caring about their guests makes your visit to a wonderful place much more wonderful and much more comfortable.