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.

Helen was super helpful providing clear instructions for checking in and out & communicating fast and efficiently! The place was clean and peaceful to stay at. Would definitely recommend to friends and family!

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!

We have stayed at this location many times in the last few years. It is always clean and comfortable and Diana is very easy to communicate with! We love staying here it is so cozy! Thank you Diana!! Perfect as usual!

We had a great stay. Exactly what we wanted in a cozy weekend getaway!

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!

Kira’s place felt just like home - comfortable, clean, warm, and lovely. Kira was also very responsive and kind in all her communications with us. We would absolutely stay again, without a doubt!

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!

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 have family in Springfield so staying at Whitney and Alex’s place is perfect for us. It’s spacious and comfortable. This was our second stay and we will definitely be returning.

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.

We had a great experience here. Anne has curated such a lovely space and it was the home base we needed to resting and work out of. I’ve rarely a host put so much effort into anticipating the every want and need of their guests - she was responsive and helpful at every turn. Would highly recommend staying at this little oasis!

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!

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.

This was our second stay with Jay & Heather. They are a fantastic couple that has an awesome place for guests to stay. They make our stay easy and are convenient to everything we need. Breath-taking views that will help you disconnect and help you get lost in thought.

We had such a lovely time staying at George and Annalee’s! The breakfast was excellent, including catering for us being vegan, and they gave us great local recommendations. They were really hospitable and friendly including picking us up from the bus stop in town! We really enjoyed our stay and would definitely stay there again.