Great stay for parent’s weekend

We loved this converted barn. The owners are extremely nice and helpful. Location is fantastic. Only reason for 4 stars instead of 5 is just that the rooms had a tendency to be very humid.

A lovely historic barn conversion that included many thoughtful touches, such as bottled water, coffee, tea and spices in the kitchen, plenty of towels, house slippers, and plenty of pillows. We stayed for two weeks and the only hitch we had was occasional hiccups with the Wi-Fi. Dan and Anita were very attentive and helpful when we brought the issue to their attention and helped us to resolve it. The location is great- you can drive to Tanglewood, Great Barrington, Millerton, Hudson and other towns for entertainment and relaxation. Would recommend.

My family loved the this place. Definitely more than I expected. Spacious and gave us eveything we needed. The host was very responsive and worked with me on check out. We were there for a regional track meet and they allowed a later checkout to attend the last day of events.

We very much enjoyed our stay here, including seeing from the 2nd floor deck all the deer and birds that elude us at home, the cozy feel of the converted barn, the kind invitation to partake from the kitchen garden, being steps away from a well-stocked small supermarket and local shops, and being welcomed to share in all that the property offers.

This was our second stay at the chalet, and hopefully we will return soon. The house is clean and tidy and comfortable. The living quarters upstairs make it feel like a treehouse - perfect for reading, playing a game, drawing, having a cup of coffee, etc. We enjoyed the wildlife and quiet as well as the convenience of walking to dinner and the brewery. An ideal getaway spot!

We and our toddler met up with friends for a long weekend away. It was an easy, scenic drive from NYC. Some people skied mornings at Butternut and Catamount, and very much enjoyed it. My toddler loved the local library, the toy store in Great Barrington, and tramping around in the yard and wooded area on the property. Even though the kitchen is small, it had everything we needed to make dinner both nights. The house itself is charming and extremely well maintained. We couldn't be happier, and would definitely return.

The house was exactly what we needed for a ski weekend in the berkshires. It was clean, comfortable and spacious enough for our family of 4. Its 5min from Catamount, 20 min from Great Barrington and we found 2 good resturants that were easily walkable at night. Anita and Daniel were responsive and accomodating. We will definitely rent this property again.

We enjoyed our stay very much. It was very clean, warm and comfortable after a day of skiing with young kids! It had all the amenities we needed. Beds were firm yet comfortable. The carriage house had tons of character and was very well maintained. Location was quiet and close to a grocery store and great pizza place! Kids loved it. We will be back! Thanks Dan and Anita :)

Everything was great with our stay. Nice cozy place and owners were great to work with. My very small thing to point out are the mattresses are a bit on the hard side for our comfort . Personal preference will be different for someone else I am sure.

The carriage house is cozy, well equipped with all the amenities you need, and absolutely spotless! Nice quiet neighborhood and town, we enjoyed our stay, with activities in the area. Thank you!

Near enough to walk to the center of Hillsdale (which has some fun stores to browse and shop in), this lofty house has enough room for the family to be together but still have a sense of space! Clean, affordable, and easy to travel in the area from. We will stay again.

We had a great experience and it exceeded my expectations. We make a yearly trip to this area and have already planned on staying here if it is available. Would highly recommend this location

We returned to Hillsdale, NY for the Roe Jan Biking event. It is really convenient to stay at this chalet/cottage. We can have breakfast here and pack up our lunches before heading to the trail. It is consistently clean and the grounds are beautiful. The tv system is Roku which we don't use at home. We hope to return soon for more biking..

The home was perfect and exactly as described. Comfortable and cozy. A nice quiet neighborhood with local shopping, restaurants and not far from anywhere we wanted to visit. Dan and Anita are lovely people and fully accessible if needed. Checking in was a breeze. We highly recommend staying here.

We truly loved put visit. The space was perfect for us and had so many lovely elements like the walkable grocery to scooting to the playground to all the state parks nearby have to offer. We loved it and definitely will be back.

This is a very nice rental. The unit is spacious and quiet. The location was great for us, with good access to Tanglewood and to wonderful hiking in Taconic State Park (NY) and to several state forests on the Massachusetts side. Keep in mind that it is a duplex arrangement and that there are stairs. The bedrooms and bathroom are on the ground floor, and the kitchen and sitting area are upstairs. If stairs are no issue for you, then you will enjoy this carriage house.

Everything about the house was clean but unfortunately it smelled like a barnyard. Very bad smell inside. The internet was down the first night and morning which was a major problem but they attended to it. Nice and responsive host but it was overpriced for the smell. Also it is near a main road not in the country so you do hear traffic.

Stayed in this quaint carriage house for a college roommate reunion. The size was perfect and the location was great - close to hiking and activities in both NY and MA. The owners were very responsive when we had questions and gave good suggestions on activities. Our only suggestions would be to have travel sized toiletries in case guests forget and new linens - particularly on the queen bedroom. Thanks for a lovely stay.

The carriage house is a fantastic getaway destination for anyone who wants comfort, coziness and tranquility of beautiful surroundings. It has everything you need for meals. The yard is expansive and beautiful. Bedding is great. Washer and dryer are a big plus for longer stays. Kitchen as everything you need. It is an easy, 5 minute walk to a nice pub / restaurant (The Hillsdale House), the local full service grocery store, a wine & spirits store and much more. And the hosts are absolutely the kindest, most responsive and professional hosts I've had the pleasure to experience. I had a few special needs and requests and they bent over backwards to help me. 5 Stars - I highly recommend!

The carriage house is a fantastic getaway destination for anyone who wants comfort, coziness and tranquility of beautiful surroundings. It has everything you need for meals. The yard is expansive and beautiful. Bedding is great. Washer and dryer are a big plus for longer stays. Kitchen as everything you need. It is an easy, 5 minute walk to a nice pub / restaurant (The Hillsdale House), the local full service grocery store, a wine & spirits store and much more. And the hosts are absolutely the kindest, most responsive and professional hosts I've had the pleasure to experience. I had a few special needs and requests and they bent over backwards to help me. 5 Stars - I highly recommend!

Cozy home that was about 30 minutes to all we wanted to see and visit. The chalet had lots of character and well appointed. Owners were close by but not intrusive. This was a great location for a friend’s get-away.

Cozy home that was about 30 minutes to all we wanted to see and visit. The chalet had lots of character and well appointed. Owners were close by but not intrusive. This was a great location for a friend’s get-away.

A perfect location where the arrival of spring is a glorious event. Walking or driving in this region is a feast for the senses. Wildlife surrounds and is to be enjoyed.

A perfect location where the arrival of spring is a glorious event. Walking or driving in this region is a feast for the senses. Wildlife surrounds and is to be enjoyed.

This is our 2nd stay at this beautifully designed house in Hillsdale. The house is close to everything— markets, hiking trails, restaurants— and is well equipped with every amenity. The owners, Dan and Anita, are easily reached and answer every question promptly. They are a pleasure. They are generous with basic supplies, anticipating their guests’ needs. The TV offers many channels— no shortage of entertainment. The house is spacious and very comfortable in every respect. Lovely views as well. We loved our stay and will happily return when we want a get-away vacation in the countryside.

Hi, We needed a place that was near ski hills + plus gave me the ability to work in a quiet place. My family would go out skiing and I stayed here to work -- it was perfect. When I was done working, I walked over to the Rail Trail and was able to get some steps in. One night after work, my husband and I went for a walk but found ourselves in the cool, hip brewery near the property. We enjoy the brewery -- such a great spot and their Porter beer was fabulous. Another benefit of this carriage house is that you are also walking distance to a grocery store. The carriage house feels very European to us. Everything was fantastic! One point that we discussed (because my husband cycles) is that anyone that wants to cycle the Harlem Valley Rail trail could cycle and stay here...its that close.

We had a great time during our 4 day stay at Hillsdale and this was to a great extend thanks to our wonderful Swiss Chalet! We also had the pleasure of meeting our hosts, Dan, Anita and their two daughters, who were super friendly, caring and very interesting people. The chalet is in a central location at walking distance from Hillsdale supermarket, the local Diner, Brewery, and beautiful Rail Trail. It is only a few minutes drive from Catamount Ski Resort, which was the main reason for our visit. The chalet was very warm and comfortable for all our skiing equipment. We will do this again soon and hope the Swiss Chalet will be available to rent the next time we go skiing at Catamount.

Having stayed at this house three times, our familiarity and fondness for it has only grown. It is withing easy walking distance to the center of Hillsdale, and only a short drive from Catamount and a little further on, Great Barrington for a complete Berkshire experience! Dan and Anita are excellent, thoughtful, conscientious hosts; quick to reply to queries and the upkeep of the house. We are glad this is one of our vacation go-to houses! Lisa

The space is lovely. Spacious, uncluttered, but has everything you'd need. Exceptionally clean. Smells wonderful (which I loved), and tons of heat (which you can turn down). Close to everything you'd want to do in the NY/ MA Berkshires. Owners are there if you need them.... and that's all. Only suggestion I have is maybe providing info about how the key holder thing works. Took a little figuring out. But then we were fine.

We loved this house! The house was impeccable. The owners gave a lot of thought to preparing the house to make it cozy, well-appointed and easy to settle right in. The location was perfect - we spent two days skiing at Butternut and exploring the area. We would definitely stay here again. Thank you!

This is a wonderful, spacious vacation getaway, with the rather unique arrangement of bedrooms on the first floor and kitchen/dining/living room on the second. Everything is super clean and comfortable. The hosts were gracious and responsive to any questions. including taking time out on Thanksgiving to text us directions to the nearest entrance to the Harlem Valley Rail Trail, an absolutely gorgeous paved trail that sits on an old rail bed and passes tree farms, goats, silos, foothills, and mountains--the entrance is only a block away. We had Thanksgiving with 35 in attendance at a cousin's house, so it was nice to come back to this cozy space and chill. We were treated to a late fall snowfall, which transformed the roads around Hillsdale into a vista of winter-sparkling fields and barns. Five stars and two enthusiastic thumbs up.! We fumbled a bit with the lockbox, but once we figured it out, there were no problems. The instructions for that might have been a little clearer, but other than that, everything was superb.