Guest house holiday rentals in Berkshire County

A wonderful place in the country. A Berkshires hideaway. A close walk from the AirBnB is a great breakfast spot - The Store. tasty pastries, coffee and entrèes. It's the second Spring we have stayed there. We noticed that the bathroom was renovated from a tub to a walk-in shower. Good move! Weather this May was chilly and wet. We hiked Appalachian Trail anyway. One caution for seniors: the bedroom and bath are on the second floor up a narrow metal spiral starecase. Hard place to lug suitcases up the stairs. If you are seasoned backpackers, no problem.

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

We absolutely loved Maple Hill Farms. It's a wonderful place and a perfect choice for a trip to the Berkshires if you're an animal lover. The best part of our weekend was bonding with Philip's sweet and friendly donkeys! The studio is well laid out with everything you need, the farm is beautiful and peaceful (except for the roosters, haha!), and the location is great for visiting local sights like Mass MoCA and The Mount. We hope to be back!

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!

Loved Mary's guesthouse! Great hosts who helped me with luggage. Beautiful surroundings with gardens and pool. Bed was super comfy and host provided coffee and fresh milk made my stay even better. Perfect place to stay for a visit to Williamstown!

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!

We came up for a weekend in the Berkshires and Galina’s place is perfect. It’s very clean and in beautiful surroundings and we had a lovely time. Highly recommend!

The Nest was a great spot for us to rest and recoup before our NEYC day! Mary was easy to work with, communicated well, and provided a great space with so many thoughtful extras!

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!

We had a great stay at Jaryn's place. We got to enjoy the pool and loved that it was so peaceful and private. The location was perfect, close to downtown Great Barrington. We slept comfortably and it was so quiet. We even got to see a bear driving down the main road!

What an experience! Thank you to Graham and Alex for making us feel right at home and super comfortable. The studio is beautiful and it’s just below where you stay. There’s a kitchenette with all you need to cook as well as a fridge and freezer. The propane fireplace was a really nice touch to make the place feel extra cozy. Working with Graham at the studio was the cherry on top. Super friendly, accommodating and a very skilled producer. Sometimes when working with someone, you’re unsure of whether they can provide highly technical skills. Graham worked quickly and efficiently. And it was amazing to hear the track that I was hearing in my head out loud! Thank you Graham and Alex. I hope to be back again :)

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!

This is a beautiful, peaceful guest house on a gorgeous property within walking distance of town if you like to walk. Very convenient and well appointed with the gardener house nearby. Geoff and Cindy were wonderfully accommodating and included many nice touches for guests. If you like a quiet, peaceful place to stay in a beautiful place surrounded by nature, this is it!

This was the perfect place for our 4 sister annual reunion. The surroundings are peaceful and gorgeous, rural and private. The interior was remodeled with every perfect touch, comfortable furniture for 4 to sit and gab, 2 separate sleeping and bathroom options. Slippers were provided and the frig was stocked with some refeshments and ice! Although it was not warm enough to swim in the lovely pool, we did enjoy sitting on the back deck and listening to the sounds of birds in the nearby field. Will and Garrick were attentive and available while being supportive of our privavcy. We really enjoyed our stay and definitely plan to return!

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!

We stayed at Chris and Dawn’s place while traveling to Lenox for a wedding. The house was even better than expected. The setting was charming and the house was more than we could have wanted. The screened in porch was a great place to enjoy the outdoors, eat dinner and lounge while also being protected from the elements. It’s within walking distance to town and only a short drive to Pittsfield. We enjoyed the farmers market and local restaurants. Both Dawn and her husband were accommodating and kind. I would happily rebook should we find ourselves in town again!

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.

Abigail offered lots of recommendations and was very quick to answer all our questions. The location is great, and the unit was lovely. The photos don't do it justice. It was spacious and well laid out. We'd stay here or elsewhere with this host again without hesitation.

Abigail is a very accommodating host! She is very responsive, friendly and professional. Abigails home is clean, well furnished and very comfortable. We will stay again should we find ourselves in the area in the future!

Comfortable apartment. Very central location in the Berkshires. Friendly and helpful host.