Barn vacation 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!!

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!

A beautiful place, spectacular views and a peaceful location. Not far from Great Barrington with views of the mountains from many rooms. The renovated barn (feels newly built) is near skiing, hiking, Great Barrington shopping and wonderful restaurants. —something for everyone. The kitchen seems to have been built for a professional chef. It is large, in pristine condition, and has everything you need to prepare meals. Very impressive! Also, there is a wonderful large bathtub for guests to enjoy the calm of the Berkshires, soak after skiing or relax after a long drive. All the bedrooms are of good size with plenty of room to move about. No bedroom is small which is terrific for an adult group. Definitely, a positive and differentiating feature. The living area space is open and is inviting. Stella was absolutely lovely and a most gracious host. All communication was very easy. A fabulous stay; we will definitely return! I could not recommend more highly.

We felt at home as soon as we opened the door. Very comfortable. Great linens. Very clean and comfortable. We love the area. Can’t wait to return.

Tracey was extremely responsive and communicated in terms of gaining access to the Roost which was beautifully appointed and quaint. They had a bottle of wine and some breakfast foods (turkey sausage and charcuterie waiting for us in the fridge) when we arrived which was appreciated. The space was well cleaned, spacious and with wonderful touches. It felt homey. Thoroughly enjoyed the stay and would definitely stay again if ever in the area.

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 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!

Can’t say enough good things about our stay! We visited over a long weekend which was perfect- it’s just a short drive for anyone looking to escape city life. The barn apartment was the perfect size for a couple or small family. It was clean and practically brand new, with a great projector for watching movies with some popcorn. We spent the days going into downtown Hudson, walking around the Olana property, and visiting a local brewery in the town over. We’re already talking about our next trip up this summer! Even though we stayed while it was snowing, the host had everything we could need including ice melt for the walk way etc. We were so impressed by everything the property provided, which made it a care free weekend!

This home is incredible and has a fascinating history. It was exactly what we needed for our escape from the city. The hosts were kind, responsive, and super helpful. Thank you!