Guesthouse holiday rentals in The Berkshires

I was looking for a quiet place to stay a couple of days and Judy and Bob's place was the perfect place. Located in a very quiet neighborhood and near the town beach, it's a great to relax. Judy and Bob were very friendly and made me feel at home.

An incredibly charming, rustic, simple and comfortable small cottage, in a gorgeous rural setting. Just as advertised. It was perfect. Right across the road is Tivoli Bays, with beautiful trails for walking and hiking, and a small waterfall too. If you like, it's just a short walk to Broadway, the main strip in the village of Tivoli. You'll find a few restaurant options, a small market, sandwich shop, excellent coffee, and homemade ice cream. I met Yuko who couldn't be nicer and was a pleasure to chat with. A great experience all around - highly recommend booking a stay!

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

What a wonderful and unique space. A wide open room with a cozy bed area. The kitchen is well appointed as well. Just a short walk to Northampton's downtown but quiet with lovely gardens all around.

A cozy spot that comfortably houses three adults, it's right on the river so it's perfect for fishing. While it feels remote, there are amenities close by like restaurants and grocery stores. And Bruce was a fantastic host, very friendly and helpful. I have no doubt we'll return.

What a perfect private getaway! Truly immaculate. Spacious. Comfortable. Peaceful.

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.

Had a lovely stay. One of the closest properties to the Main Street in town, so you are able to relax in a quiet space but also go to and from town as often and as easily as you’d like. Host was very communicative, offering flexible check in and check out as well as local recommendations. Highly recommend.

beth was wonderful. the place was great. she was so sweet and kind and made sure we had a great weekend. would definitely recommend. the pond with fish was fun to feed them. the little recommendations book she made was very helpful. we were there for an event over the weekend and it was very relaxing and we enjoyed our time.

The house is very comfortable and feels like home. The kitchen is spacious and well-equipped — a great experience for cooking. There’s a peaceful courtyard that’s perfect for calming your mind or reading a book. One night, we even spotted a bear from the window! It’s a great location, and don’t worry — the bears are vegetarian. Elisa and Mickey are very kind and responsive. They’ll even create a personalized list to help you explore the town, even if you’re not familiar with the area. You can shop at Taft Farm — my favorite local farm. Cooking at the house really made it feel like home, and also “farm to table” experience. Thank you!

Great experience! 2 wineries within 1 mile. Close to great hiking. William, was very accommodating with check in & check out time. Would highly recommend staying here. Very cute , clean and comfortable with get amenities.

John and Molly were fantastic hosts - responsive, friendly and extremely accommodating. The space was beautiful and matched descriptions + photos! It’s in a central location in downtown Toga - close to most restaurants, bars and shops.

My husband and I arrived late, around 9:30pm, because we had commuted after work in NYC. Everything was impeccable. The home is perfect in some many ways. We felt very comfortable and got an amazing night's sleep. The following more we had to head out early to pick our daughter up from Binghamton. She stayed with us on our second night. Nicolette's and Tim's Tiny Horse Barn is so perfect. It is exact amount of space we needed. Even though the space is space, there were 5 tissue boxes in perfect locations. This may seem a small thing to some. But if you have allergies, it is SO appreciated. The kitchen was equipped with keurig coffee pods, creamers, sugar, tea kettle and more than everything we needed. Equally the bathroom was perfect. The beds were super comfortable as was the temperature. There were plenty of great restaurants nearby. The attention to detail is amazing. Everywhere there are little hints of horses, but not in an overwhelming way. We actually are having book sent :)

We were day hiking the AT in the Kent to Cornwall area and stayed 3 nights at the Lodge. The lodge was comfortable, roomy and equipped with everything we needed. Brooke was great to talk with and very responsive to our requests and questions. My only regret is that we did not have enough time to explore the grounds of the estate which appear to be amazing and have a very interesting history. Highly recommended

We had a great night hear. It is a wonderful town. We were at an event at Williams College and were able to easily walk there. There are plenty of shops and restaurants along the way. The area is beautiful. The space is amazing. Perfect for couples. We appreciated the treats and milk. The host was responsive to the only question we had and answered everything immediately. The instructions are exquisite and well planned. If you are in the area this is a great find.

Our stay at Kelly’s place was fantastic! We stayed here last year and loved it so much, we decided to stay again this year. It was very cozy and we felt right at home. Everything was very clean and Kelly thought of all the little details that made our stay that much more pleasant & relaxing. Her place is a peaceful oasis, very quiet & private and the beach access was our favorite. Kelly was super responsive and allowed us to extend our stay for an extra day so we could enjoy one more day in the area. Overall, I would highly recommend staying here.

Dawn set the bar high with this Carriage House. Fully stocked, updated, comfy, quiet, impeccably clean, high end everything. This was our first stay at an airbnb, I can't imagine they are all this new and this nice. Next time business or pleasure takes us up your way we hope to stay here. Thanks, J&B

We were stunned by how magical this place was with all it's uniqueness of historic house. Spotless clean, spacious, very friendly owners. Our kids loved running around the back yard and playing board games that were provided. We would definitely come back, the only thing we regret is that we couldn't stay for longer, the area is very picturesque. many thanks!

I hope John will rename the place “The Cow House”. We enjoyed watching the cows every morning over coffee as they work their way across the property. While I love the windows to see the magnificent scenery (including cows) I wish there was a curtain option upstairs - 05:00 sunrise can be rough. The hot tub was fantastic and we got a chance to be in with the evening mist at dusk. We really enjoyed our time.

My fiancé and I stayed at Lambs hill to celebrate our anniversary. We had the most wonderful time. The views are breathtaking. The wrap around deck with jacuzzi and hammock made our stay calming and serene. I loved seeing the horses and donkeys throughout the day. They made the experience even more special and unique. Charlotte was super responsive and accommodating. We took cabs to Main Street at night for dinner and drinks and it was so close and convenient. I left my heart in lambs hill and can’t wait to return one day.

The Eco Cottage was a perfect, tiny gem tucked away in the middle of the beautiful green woods. It was so private, peaceful, and serene. It truly felt like my own little retreat and since I was there to go on a retreat, this was the perfect place to lay my head at night. I loved walking the trails and wow, the pool, which looked so inviting (even if it was a bit too chilly to use this time!). Everything was clean, and the instructions were clear and easy to follow. Hosts checked in regularly but gave me my privacy. I really enjoyed my stay SO MUCH and will absolutely be booking here again the next time I’m in the area. Highly recommend!

I can't imagine staying anywhere else, Jeff and Dawn set an extremely high bar. The home is beautiful, clean, and as described. Jeff is responsive, warm, and wonderful to talk to. We will absolutely be staying again, I can't thank you enough! See you again soon!

Easy to find, key pad entry, clean. Graham left some fresh eggs from his hens..nice touch. Quiet spot in a natural setting.

Great space and extremely comfortable. Easy and pleasant communication with the hosts. Would definitely stay again. Make sure you stop at Singletons General Store, it’s amazing. Short drive to the town of Ludlow, Buttermilk Falls and other areas.