Farmstay holiday rentals in The Berkshires

Nick & I absolutely loved our stay at Dave’s Milk Barn. It was charming, adorable, cozy, and gave us exactly what we needed for a respite from the city. Rio & Toby were incredibly flexible, kind, accommodating and helpful. Beautiful surroundings, adorable quaint rustic accommodation. We couldn’t give this place enough positive marks! Will definitely be coming back.

Bernard’s home was perfect and just as pictured and described on Airbnb. He was very communicative and flexible with check- in and check- out although I did not need it. I would definitely stay at the farm again!!!

Fantastic space for a large group. We had 10 people for a New Year’s Eve ski weekend, and this was the ideal spot for it. Hot tub was a great treat. Be warned - the floors are squeaky, so if you’re a light sleeper in a large group bring ear plugs.

We recently enjoyed a lovely stay at The Carriage Barn in Guilford. Our host, Katherine, was very responsive to everything we might have needed during our visit: a very easy check in and out process, detailed instructions on how everything worked, items for our comfort (a gift of delicious chocolates, many fluffy towels, silky sheets, etc.), and was easily available via texting. The photos of her restored historic barn are very accurate - it's a beautifully designed renovation and is decorated with lovely art pieces, cozy furniture, and a huge library of books for your enjoyment. The tv works great and so does the WiFii. We traveled with our small dog and there is a baby gate available that easily snaps onto the staircase posts so I was not concerned about my dog's safety.. Best of all is the beautiful views of the gorgeous Vermont countryside. You'll see lovely sunsets here and spectacular sunrises. It's a great spot to truly relax.

We enjoyed a beautiful early spring stay on the farm with a group of 7 ladies, gathering for a chill bachelorette weekend in Cold Springs. The farmhouse was super cozy; great for cooking, crafting, games, tea time, outdoor wine picnics, star gazing at night in the hot tub and making friends with the chickens! A great retreat spot for groups with all the amenities!

Scott’s house was one of the best airbnbs we’ve ever stayed at! So unique and cozy. Very clean and beautiful location. Will stay there every time we are in CT

We really enjoyed our stay at this lovely house!! So many cozy nooks and Miles and Ruth were very responsive and helpful hosts! Would definitely stay again :)

This is the best AirB&B we have ever stayed at! Tom and Julia are wonderful friendly hosts who create a warm and inviting space. The farm and property is breathtaking, and it was so fun getting to feed and pat all the animals! Special thank you to Eyore and Millie their donkeys who are the sweetest. We look forward to coming back in the future. 10/10, no notes.

The other reviews are spot on. This place is lovely. The house looks and smells fantastic. The town is very close by and Richard is a great host. Everything was exactly as desired and very cozy. We were even treated to a winter snow storm which made the place even more magical. Would love to return in the future!

I highly recommend this property. Beautiful country setting yet convenient to the city. This is probably the cleanest Airbnb I’ve ever stayed in and had the best equipped kitchen for those wishing to cook. Thomas was very responsive and professional.

The epitome of charm!! The house is a lovely space & the farm is beautiful! Though the weather didn’t quite cooperate with all of our plans (snow in April!?!) we were cozy & happy at the house! Took a walk to see the cows (& calves ❤️) & purchased honey, meat & other products in the farm store. Deer & a bobcat also added some excitement. Can’t wait to go back again! Thank you Sarah & Jeff!! (& Whiskey the sweet farm dog!)

Carrie and her family were absolutely wonderful! I felt comfortable and welcome while staying at their cabin. The view from the cabin porch is breathtaking. Carrie had given us a tour of the barns where we were able to meet her husband and children and all of their wonderful animals. We were introduced to all the barn dogs as well who were so friendly! If you are looking for a place to feel away from it all, while still being close to local towns. This is the place for you. Thank you Carrie and your family for making this stay feel like home. Looking forward to staying again!!

This is an incredibly special place to stay and perfect for a fun family weekend away!! It is an old-school Airbnb in the sense that the hosts are genuine people who want to share their beloved, fascinating space with others. Michael and Jody went above and beyond to make us feel welcome on their unique property. The shipping container house is awesome, very comfortable, and has everything you need. They provide so many thoughtful touches (coffee, games, plenty of towels, laundry detergent) and are very proactive with helpful texts with local recommendations. You can feel the powerful history of the land as you walk around beneath tall trees. Michael was so kind and generous with my two young kids, taking us around the property and into the greenhouse, pulling from his vast experiences to engage them, and he even got my son to eat microgreens! We were delighted by the experience! There are hikes nearby too—Ashokan Quarry Trail is perfect for kids—and lots of great restaurants around.

The cabin exceeded all our expectations! It had everything we needed to feel at home, and the farm and trail behind the house is well worth exploring.

We had a great time staying there. Everywhere was so clean. I had all the cooking utensil I needed. We stayed in and played around the field. We would love to be back again.

We absolutely loved this house and its beautiful and peaceful surroundings and would definitely stay here again. Much love and thought are put into every detail of the house, and it was immaculately clean!

There were so many additional amenities that were not required but were provided, that helped the entire trip 10x more. Anything you could have forgotten, they had for guest. The animals were a big plus and I thought that I may have wanted to put the cat up when I first read but that part of this experience was one of most heart fulfilling and peaceful parts! The view from the hot tub is immaculate and the hosts were even better! They were so welcoming and made me feel so comfortable with the animals. Overall I’d give 100/10.

From the time of booking the hosts were great with communication. Check in went smoothly and the home comfortably fit our group. If visiting the area for NY Sheep and Wool this home is a continent location.

Highly recommend, beautiful cabin with great amenities! We enjoyed our stay here and would come back!

We had a fabulous stay at Amanda's place. It was so quiet, peaceful and the scenery was just so beautiful. We felt relaxed the moment we entered the property. It's definitely a place where you want to take it slow, watch the sunrise and admire the landscape and nature. The apartment had everything we needed and more. Lots of thoughts and efforts had been put into the place to provide for a very comfortable stay. Amanda's communications were excellent right from the beginning till check out time. She also provided a folder filled with useful local information and recommendations. Many of the amenities Amanda provided were not only environmentally friendly but are also very high quality products. Even though the apartment is attached to the main building, we still had our own complete privacy and there's very little noise at all from the main house. We will be happy to return again whenever we are traveling in the vicinity.

A great long weekend getaway! Loved the hot tub! Host was very friendly and responsive!

We loved the cottage. If anything it was even cuter in person than in the pictures. Communication was perfect and the place was very well thought out. We enjoyed our stay, I’d recommend it and come back here in the future!

Steven is a great host, friendly and responsive via text—even helped us with shoveling and brushing snow off our car without being asked. He has clearly put a lot of love and care into restoring this historic home, which has a lovely view of the creek and great birdwatching. Bc most of the furniture is antique, this home is light on cozy places to lounge in, but a great home base for days spent antiquing and enjoying the beautiful nature in this part of the world.

It was perfect - clean, quiet, easy to find and get into. And the best part was I got to meet one of their dogs at the very end of my stay