Tiny house vacation rentals in Columbia County

Beautiful space with lots of character, in true spirit with the Berkshires way. Thank you!

Stayed in the guest house for the night, and was a peaceful and pleasant stay! Hosts were very friendly and amenable — watching the goats was a nice bonus as well!

Merry is a sweet woman who is a very caring pet owner. She is knowledgeable about the area, sharing many excellent tips, especially in regard to restaurants. We took her suggestions & were extremely pleased with the results. We look forward to visiting again in the future. Thank you Merry.

Beautiful little a frame! Peaceful property with lots of little things to do to tucked around - would love to come back and use the pizza open on the summer! The communal bathroom and kitchen area was beautifully designed and a short walk from our cabin. Appreciate the extra touches (firewood, ability to use sauna, s’more kits) note that these are for an extra cost. Thank you!!

House was so gorgeous and well appointed with quality, high design things. Was so relaxing and a great view with all the comforts. All of the appliances you could think of- multiple different ways to make coffee, froth milk, blend, toast- had everything!!

I would 1000% recommend Adam’s place. The house was really charming, well designed and super comfortable. The entire property/land was unreal and the views were beautiful. I’m still thinking about our stay and wish I booked a week! Do yourself a favor and stay here.

This place is amazing, cozy, and fun. I hope to return one day.

Loved our stay! Was the perfect weekend getaway. My husband and I love to camp (me more glamping lol) and this was the best of both worlds. Jordan was a great host, very responsive and helpful. There is no lock on the door to the tiny home which may bother some but we were fine with as I thought of it as a camping experience. Highly recommend this stay! Beautiful tiny home and surrounding trees.

Hello - Great to be back in Maureen's home. Super excellent location 5mins or so to Great Barrington and close to everything the Berkshires has to offer. Home is really amazing for a romantic weekend away, my partner and I both loved everything about the home and the surrounding property. no notes.

I genuinely can’t say enough about this place. It’s absolutely beautiful! Thoughtfully designed, super clean, and filled with the kind of details that make you feel at home. The plants throughout the space add such a calm, lived-in vibe, and the views are unreal. The outdoor areas were perfect for lounging while it was warmer (we visited mid April) but it’s definitely a spot you can enjoy in any season! The bathrooms and appliances, the WHOLE place is all super modern and brand new, but still feels really cozy and welcoming. And the host are truly one of the best we’ve ever encountered. So kind, so responsive, and even sent over local event links to help us find cool things to do in the area on Easter Sunday! We’ve stayed in a lot of Airbnbs over the years, and this one is easily in our top 5. Zero regrets booking it and we’re already looking forward to coming back!

The property precisely matched the online photographs, providing an immediately comfortable and welcoming atmosphere. Its cleanliness was noteworthy, and we were pleased from the moment of arrival. The provided instructions were clear and concise, and the host's suggestions proved invaluable. The morning sounds of roosters added to the overall charm. would definitely recommend.

We loved our stay at Cozy Grove. It was as lovely as the photos and had everything listed and more. Spotless— really, truly clean. All the little touches: coffee bar with yum beans, robes, a hot tub that works! filtered water, cozy blankets and pillows, that couch! Spices, salt, oils, but no fridge clutter. Everything we needed to cook and bbq. We enjoyed the recs for restaurants and antiquing, but we mostly loved relaxing and enjoying the house most of all. Planning our return!

This is our second time staying here, we loved it so much the first time. We definitely recommend staying here for a quiet, peaceful, beautiful getaway!

We enjoyed our stay! The cabin was private and so cute. It was just as described. When we arrived, we called Silivia to confirm where we could go walking— she answered peomptly and was very helpful. Would recommend. Would come again. Thank you!!

If you’re looking for a cozy relaxing little getaway house, this is it. We had such a wonderful stay! The place was exactly what we needed for a relaxing weekend, and I truly enjoyed my time here. Everything was perfect, and spotless. The hosts have wonderful hospitality and gave us recommendations for the local restaurants etc. I hope to be back during the summer and will definitely be looking forward to staying at this place again.

Truly MAGICAL!!! I had booked Roger & Tony's Magical Island a couple months ago to celebrate mine & my husband's 15YR Anniversary and it exceeded all expectations! It was the PERFECT place for us and our 2 Labs to enjoy a quiet, peaceful escape to enjoy ourselves and nature. It is quite a unique experience to be out on your own island getaway and I HIGHLY recommend it! They were very communicative & responsive with great recommendations and instructions. The home is as warm & cozy as described and photographed, but actually bigger than expected. The kitchen was great and we cooked every morning's breakfast and grilled one night's dinner. The living room was super cozy and one night we watched tv on their projection screen. The upstairs bedroom was HUGE with a comfy king bed and a large seating area with a flat screen tv. Cute, fully stocked bathroom. Amazing backyard with firepit, hammocks, & large table. We hope to go back during summer when the trees are in full bloom! LOVE!

House was very clean and comfortable. Loved the decor and bed was super comfortable and cosy. Everything was there in the house- kitchen, bathroom, hot water. Well styled decor. Spotless. Felt very private and peaceful. Location was not as picturesque as I prefer, but fairly close to sight seeing.

Wonderful isolated cabin. Do be prepared for camping life but the Stewart's gas stations provide easy access to ice and other supplies. There were a few things that needed fixing but the host was very responsive. Beautiful A frame. No houses in sight. Excellent view of the mountain and terrific bird life in the field.

It was a pleasure to stay at the cabin! Deborah was such a great host! Walked in after a 3 hour drive to treats and fruits. She was very helpful explaining and showing were everything is! Location was close enough to town and far enough to be peaceful and quiet! Loved this cabin!!

Overall, we had a great time at Todd’s cottage and exploring Hudson. Todd had great recommendations for local wineries and restaurants to visit. I can tell this would be a great place to stay as well. He also has a charming cat named Hemigway on the property. The start of our trip had a rocky start - the water wasn’t working due to a frozen pipe. Todd quickly had the next door cottage made available for us. We ended up finding mouse droppings there, so Todd allowed us to access both cottages at once to resolve the situation. The weather got warmer on the next morning, so water started working again at our original booking, so it all ended up working itself out. Through all this, Todd was a great communicator, fast to respond, and very flexible. Thanks again for hosting us Todd!