Holiday rentals with breakfast in The Berkshires

I had a wonderful stay at The Nest house in Kerhonkson. The home was clean, well cared for, and incredibly comfortable — the straw bale construction provided the perfect environment for me as I am sensitive to air quality and temperature. I truly felt more at ease here than I have in quite some time. I am primarily homebound and came up from the city to try and get some fresh air and nature. The property was perfect for this. I spent many hours on the couch watching birds, a fox, a woodchuck, and the trees out the window. I even managed to spend a bit of time out on the porch, listening to bird songs, the wind chimes, and the wind in the trees. It was the perfect setting to relax and recharge. Kristin was an outstanding host — accommodating, communicative, and kind — the check-in process was a breeze and she was very responsive to my mobility needs. This was a healing and restorative space, and I would absolutely recommend it to anyone looking for a peaceful retreat close to nature.

Anne’s place is truly incredible with the design and amenities. Perfect spot to be secluded for the weekend and check out neighboring towns. She very generous by preparing breakfast each morning you are there and has great communication/check-ins. Amazing getaway!

We were extremely pleased with Shinto and his house. The house and the surrounding area were more beautiful than the pictures could capture. Shinto was a very accommodating and I couldn’t ask for a better host. Will definitely be returning asap!

Christine went above and beyond in welcoming us to her place. The fridge was stocked and she gifted us with homemade treats at the beginning and in the middle of our stay. Her place is spacious, clean, and comfortable. We enjoyed adventuring on the walking paths behind the house and her guestbook offered wonderful tips for Brattleboro and the surrounding area. We had a wonderful time!

My friends and I loved Jenny’s home. Every corner there was something else to look at. It was spotless and we felt right at home. What a beautiful weekend in Kinderhook, felt like an escape. Cute town too!

We had a wonderful stay at Carol and Robin’s home on the lake. Anyone looking for a serene and peaceful setting would be thrilled with this rental. Our hosts communication both prior to and during our stay was top notch. We certainly hope to return someday.

Miguel is a great host. He was really helpful and responsive. His house was extremely well equipped and comfortable. The surroundings are beautiful. Probably our best Airbnb experience in the US.

We enjoyed our stay at Brendan’s house , very peaceful area , the house is old but clean and in nature we loved it . Brendan makes sure that everything goes well and gave us a lot of informations about hike trails , restaurants and things to do in the area .

Trisha’s place was the one that completely changed my perspective on air bnb, I really loved and enjoyed my entire experience as a whole. I’d definitely come back again thanks Trisha.

Tim! Our stay was Beyond my expectations! Many many thanks, appreciation and affection. Be well~ Jen, Lucia and Jack

Diane’s place is lovely! Spacious, clean, quiet, well equipped kitchen -has it all! Stayed here a few times and will definitely be back. Thank you Diane!

We had another wonderful weekend at Barbara & Chad's suite. We've stayed there multiple times and love it for our family of four. The hosts are always responsive and so very helpful. We also love the nearby Berkshire East Mountain resort and nearby local towns. Looking forward to our next visit!

was communicative and friendly! Cute place and comfortable bed :)

Very lovely place located in a nice part of town. Mary and Lance were very welcoming and nice. We had a great stay and I strongly recommend this place for staying in Brattleboro.

The Modena House was perfect for our trip. We wished we had the chance to enjoy the outdoor aspect a little more, however time and weather didn’t cooperate with us. The place is adorable, a great kitchen, nicely decorated sitting room, bathroom and bedroom made for a lovely stay. The hosts are top notch! We hope to stay again in the future if we are in the area. Xoxo

I enjoyed my stay. Felt safe, comfortable and Cheri provided and went the extra mile.

Very quiet. Brianna's beautiful light sculptures add so much to the visual beauty of the place. Echoing other reviews: the mattresses and pillows are super terrific. One challenge for us as an older couple -- the bathroom is on the first floor and the beds are upstairs. There are many well placed nightlights but it's still something to get used to if you have to get up in the night. A hummingbird came to visit!

Very beautiful and quiet house in the nature. The room is large and the bed very comfortable. Thank you Susan for the warm welcome, great breakfast and nice conversation! Recommendation for diner for future guests : Bimi’s canteen and bar in Chatham !

Tina’s place was charming and peaceful. If you’re looking for a spot to relax and enjoy a quiet getaway this is the place. We could have spent days perusing the library of books available in this lovely loft. Tina was gracious and accommodating during our visit and we will definitely return again soon.

We had a great time staying at the Lacey Rose! I appreciated the direction communication from Denise and being in a space that was so thoughtfully decorated and cared for. Breakfast made for us at the time we requested was a huge bonus as well!

We could not have asked for a nicer place to stay~~~~clean, comfortable, woke up every morning hearing the bird’s singing. Felt like home. And Lori was a wonderful host! Thank you!

Leo and Michelle were very responsive with any questions we had, and even reached out to offer us an early check in. The location was close enough to our places of interest, while still being slightly rural. The place looked just like the pictures and we felt right at home. We will stay there again when we return!

This place was absolutely enchanting. The view of the river stretched out before us, shimmering like a ribbon of silver as it wound through the landscape, creating a breathtaking backdrop. It’s the perfect haven for couples seeking a tranquil escape, offering an ideal setting for relaxation and nurturing self-care. Whether sipping tea on the patio or taking a leisurely stroll along the water’s edge, every moment here feels like a soothing embrace from nature.

Anita was friendly, hospitable and thoughtful. Her place is well curated for guests. The bathroom and bedroom is impeccable with a lot of thought into the comfort of those staying. The home is in a lovely neighborhood and within 10 minutes drive of the city center. We enjoyed our stay.