Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style
5.0
Outstanding(90 Reviews)Chalet in Hillsdale, NY
6 guests · 2 bedrooms · 1 bath
Reasons to book
Guests love it hereGuests give this property a top rating
Free cancellationFull refund if you change your mind
Includes essentialsGarden, Kitchen or Kitchenette, Air conditioner and more
About this chalet rental
Located in the heart of the Berkshires, equidistant from NYC and Boston, this newly equipped and renovated carriage house is located in the historic town center of Hillsdale, NY. The carriage house is a completely separate and private structure from the main house. You'll have a Swiss chalet-style, warm spacious living room, a cozy dining room with a wooden table fit for 6, a fully equipped quaint kitchen with modern conveniences (with pots/pans, dishes and silverware, coffee maker, dishwasher, toaster oven and microwave), bathroom with washer/dryer, balcony with beautiful view of Catamount, 2 spacious bedrooms downstairs with built-in closets (one with a queen bed, the other with 2 twins). Additional sleeping space for two is located in the living room (queen pull-out sofa). There are exposed beams from the original barn throughout the house. The entrance has a solarium/mudroom for skis, boots, shoes, hiking boots, golf clubs, and bikes (bring your own). There is a lovely decorative Vermont Castings stove in the living room. There is internet and Roku TV. Our driveway can hold up to 2 guest cars. Perfect for year-round getaways. Our guest house has easy access to all that the Berkshires, Western Massachusetts, and the Hudson Valley has to offer. You will have access to the 2.7 acres of land which are partially wooded and partially grass and include a blueberry patch, Macintosh and Golden Delicious apple tree, and blackberries which you can enjoy depending on the season.
You’ll be five minutes walking distance from the Hillsdale supermarket, a wine and spirit store, Hillsdale House Restaurant, O’s Country Diner, Mount Washington House Grill, Hillsdale General Store, Home Chef, playground for the kids, Cobble Pond Farms Gulf station, Crossroads Restaurant, Stewart’s shop, Village Scoop Ice Cream, post office, Passiflora gift store, Taconic Valley Bicycle and Hiking Rail Trail and the Roe Jan Brewing Company. Further, you are within five minutes car ride to Catamount Ski area/Catamount Adventure park, the local library, Roeliff Jansen Park (nature preserve walk, home of the Copake/Hillsdale farmer’s market) and Four Brothers Pizza Inn Restaurant. You are within a 10 minutes’ drive to Bash Bish waterfall, Copake Lake Country Club and Egremont Country Club (gulf) and Taconic State Park (swimming). Hudson and Great Barrington are within 25- and 20-minutes drive respectively. Butternut Ski area is within a 25 minutes’ drive. Tanglewood is 30 minutes away. Norman Rockwell Museum is 30 minutes away as well. Millerton Cascade Mountain Vinery is 30 minutes away. Mac-Haydn Theatre is 25 minutes away. Hancock Shaker Village is 35 minutes away. Jacob’s Pillow Dance Center is within 46 minutes away.
You’ll be five minutes walking distance from the Hillsdale supermarket, a wine and spirit store, Hillsdale House Restaurant, O’s Country Diner, Mount Washington House Grill, Hillsdale General Store, Home Chef, playground for the kids, Cobble Pond Farms Gulf station, Crossroads Restaurant, Stewart’s shop, Village Scoop Ice Cream, post office, Passiflora gift store, Taconic Valley Bicycle and Hiking Rail Trail and the Roe Jan Brewing Company. Further, you are within five minutes car ride to Catamount Ski area/Catamount Adventure park, the local library, Roeliff Jansen Park (nature preserve walk, home of the Copake/Hillsdale farmer’s market) and Four Brothers Pizza Inn Restaurant. You are within a 10 minutes’ drive to Bash Bish waterfall, Copake Lake Country Club and Egremont Country Club (gulf) and Taconic State Park (swimming). Hudson and Great Barrington are within 25- and 20-minutes drive respectively. Butternut Ski area is within a 25 minutes’ drive. Tanglewood is 30 minutes away. Norman Rockwell Museum is 30 minutes away as well. Millerton Cascade Mountain Vinery is 30 minutes away. Mac-Haydn Theatre is 25 minutes away. Hancock Shaker Village is 35 minutes away. Jacob’s Pillow Dance Center is within 46 minutes away.
Amenities
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Garden
Family friendly
Map of Hillsdale, NY
Reviews
5.0
Outstanding(90 Reviews)5.0
The house was clean and quaint and the property is on a nice quiet street. The owners were super quick responding to our texts and answered the phone a couple of times the first day for questions on the tv/internet. We appreciated that they notified us when they came up to stay in their main house over the weekend. The location is exceptional, close to the Berkshires, Kripalu, Hudson and state parks. It's an easy walk to the town, which has a good supermarket, a liquor store, coffee shop, gift shops and a bar/restaurant (Hillsdale house). We cooked dinner in the house most nights with no issues. We met Dan, the owner, who is nice and laid back. A fabulous getaway for the week and will likely look to book again.
5.0
Great location near everything. Host was always available for any questions. We enjoyed our stay.
5.0
The home was very comfortable and had everything we needed. It was also a very quiet neighborhood but within walking distance of everything in the town. We were able to meet our hosts and they were lovely. Would definitely recommend this place
5.0
Great location in Hillsdale and stones throw away from restaurants and pubs. House was as described, clean, and communication with host was good. Would stay again.
5.0
Very nice, clean, stylish place. I would come back again.
5.0
Our family of 4 (two teens) had a great stay at Dan and Anita's Hillsdale carriage house. The property was immaculate, cozy, and the bedrooms were quite roomy. Less than 10 min from Catamount for skiing and 15 min to Great Barrington. We enjoyed relaxing in the rustic style living area with exposed beams at the end of the day. The kitchen is small but worked fine for us as we did not plan to do much involved cooking. The beds are quite firm, almost like a futon, which can be a plus depending on your preference. It was a bit firm for me but my husband loved it. Very quiet and peaceful, and communicating with Dan was a breeze. A lovely stay!
5.0
This is our second time at this location and it works very well for us
5.0
My sister, cousin and I stayed here for a kid/husband free weekend. The house was clean, private, and within short walking distance of 2 restaurants and one cafe, as well as a grocery store, and a cute selection of small shops. The cidery and a distillery, as well as several hiking trails, were nearby. The house had spacious bedrooms, with firm, solid beds and linens. The upstairs was large and airy with a small full kitchen and comfy sofa. There was a washer, dryer. Our favorite spaces were the second floor deck that felt like a treehouse, and a secluded first floor covered back porch.
5.0
Great stay for parent’s weekend
5.0
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.
5.0
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.
5.0
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.
5.0
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.
5.0
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!
5.0
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.
5.0
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.
5.0
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 :)
5.0
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.
5.0
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!
5.0
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.
5.0
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
5.0
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..
5.0
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.
5.0
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.
5.0
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.
5.0
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.
5.0
Lovely Reunion!
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.
5.0
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!
5.0
Fantastic carriage house and hosts
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!
5.0
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.
5.0
5 stars
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.
5.0
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.
5.0
Hillsdale spring!
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.
5.0
Great house, excellent location!
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.
5.0
Perfect Retreat Location
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.
5.0
Excellent Place
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.
5.0
Great for a Getaway!
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
5.0
Just perfect
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.
5.0
Wonderful
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!
5.0
Thanksgiving Holiday in Hillsdale
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.
FAQs
How much does this chalet cost compared to others in Hillsdale?
The average price for a rental in Hillsdale is R 3,555 per night. This rental is R 54 above the average.
Is parking included with this chalet?
Yes, parking is listed as an amenity at Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style. For more information, we encourage you to contact the property about where to park.
Is there a pool at this chalet?
We didn’t find pool listed as an amenity for this chalet. It may be worth double checking if a pool is important for your stay.
Is Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style pet friendly?
Unfortunately, this chalet is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style?
We found 10 amenities for this rental. This includes air conditioner, kitchen or kitchenette, internet / wifi, parking, and laundry.
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