Barn holiday rentals in Columbia County

A lovely break from the city - which is exactly what we wanted. Our dog loved it too. The barn is spacious and well appointed and the grounds are perfectly maintained.

Thank you for a wonderful stay! Cleanliness is my top priority, and your property was pristine. Not only was all in excellent condition and fully functional, but also thoughtfully designed—the aesthetics truly enhanced our experience. From the carefully placed vase that highlighted the color of the floor and played off the artwork which was a feast for the eyes and mind—every detail felt intentional. I particularly appreciated the window treatments that obscured a compromised view and enhanced privacy. The space was free of clutter yet full of character. The owners were always accessible, accommodating, and kind. I would absolutely stay here again!

Charming accommodations! Even better in real life than the pictures.

We’ve stayed here a few times and love it every time. The property is gorgeous and just a few miles south of town. Best of both worlds. Christopher and Tom are both lovely and happy to help if we’ve ever needed anything.

Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

Staying at Will and Aenne's barn house was fun and wholesome. I enjoyed saying hello to the animals and the jungle shower most of all. The barn has everything one needs. Though, I must say I was very intimidated by having to light the chef's stove. We walked from the barn to the waterfall down town which was beautiful--great place to hang out and swim in the warmer months. The village of Kinderhook is adorable with quaint little shops. Hudson city had some of the best food I've had in a long time; I strongly recommend eating at Cafe Mutton. Overall, Will and Aenne were very hands-off hosts--as in, they gave us our space and privacy--while still being responsive and attentive. Thank you for the stay! I hope to come back again!

The barn was exactly what I needed for a few days away to reset. It is a beautiful home with all the amenities you could need. Julie is very intentional with the guest experience; the little touches made the stay even more wonderful. The location is perfect for access to everything Great Barrington offers, but you’re a little tucked away on a quiet, peaceful road. I loved the Old Red Barn and would recommend it to anyone passing through the area.

Molly and Gregg’s converted barn is absolutely breathtaking! I’ve stayed at many places, this one is definitely in the top three, the attention to detail alone is what makes it so exquisite, the soul of the barn is preserved while beautiful modern updates were added for creature comforts. It looks like it does in the pictures, but actually seeing it in person is on a whole other level. Very responsive flexible accommodating and friendly hosts, offered to let us stay a bit later the next morning since it wasn’t booked up. Such a magical place, would love to visit again sometime!

Just had a great stay in Great Barrington. Enjoyed the house and all of its amenities. Location was great, close to great restaurants, hiking and skiing. Would recommend this property and our host!!

Clean, spacious, well-kept, and modern accommodations- perfect for 4 people- can handle more- highly recommend!!

The space was beautiful, clean, and exactly as pictured! We enjoyed a weekend away and appreciated the local recommendations shared in the guide. We spent time exploring the farm, the surrounding area, and also were able to kick back and relax in the amazing property.

Charming barn conversation! Loved the fireplaces and hay loft as well as the silo. A unique home with lots of room for a group gathering!

This was my second time staying at Maureen’s beautiful lakeside home and it surely won’t be my last. It’s the coziest, peaceful and inspiring place. Looking forward to future visits!

This barn house is amazing!! SO secluded. SO cozy. Every single amenity you could possibly want! Very quaint, lots of antiques - but also very high tech at the same time. Coffee, tea, waffle maker, fresh eggs, stocked kitchen, comfy couch. Very helpful home and property book on the counter. I wish we could have stayed longer. FYI the hike to the mountaintop was a little more muddy and arduous than "ten minute walk, five minute hike." We picked off at least 30 ticks! But it was really worth it for that view! And it really is a 10-15 minute drive to Hudson, even though you feel like you're in the middle of nowhere. Robert was very friendly and hospitable. The house was just as described. Would definitely stay here again!

This lovely, renovated barn is the perfect place to get away.  The space combines chic, sophisticated décor with a homey, comfortable ambiance (including luxurious linen sheets, amazingly comfortable beds and the extravagance of three bathrooms with showers!) The kitchen is well-stocked and there is a charming deck for sitting or eating outside.   The location is ideal, with easy travel to Chatham, Hillsdale, W. Stockbridge or Great Barrington and all the pleasures of both Columbia County and the Berkshires.  Ricky is a gracious host who responded to all questions quickly and with warmth.  All in all, highly recommended!

We had a great stay - Monica was extremely communicative and so easy to reach out to with all my questions. The home itself was gorgeous, pristinely kept and she left slippers for all guests to use which was really appreciated. Each room had iPhone chargers which was also a great touch. Overall had a wonderful stay! Note: if you have a dog, just watch out in the backyard during summer because mine did get a lot of ticks. Not in their control at all, just a heads up for other dog owners!