Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style
Top rated by guests
9.9Outstanding
(103 Ratings)
"Beautiful carriage house, very warm with a nice common space on the second floor. Very walkable to anything in the Hillsdale proper. Check in and out was smooth. We stayed early January and it was gre..."
Guests love it hereGuests give this property a top rating
Well priced for this locationPriced under area average
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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.
Amenities at Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style
Beautiful carriage house, very warm with a nice common space on the second floor. Very walkable to anything in the Hillsdale proper. Check in and out was smooth. We stayed early January and it was great. Thank you, would book again!
10 / 10Outstanding·Oct 2025
Perfectly clean and beautiful. We enjoyed everything about our stay. While enjoying privacy we were still a short walking distance to the charming town.
10 / 10Outstanding·Oct 2025
4th time there It’s always great
5 / 10·Oct 2022
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
$$$$
Top rated by guests
9.9Outstanding
(103 Ratings)
"Beautiful carriage house, very warm with a nice common space on the second floor. Very walkable to anything in the Hillsdale proper. Check in and out was smooth. We stayed early January and it was gre..."
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.
Amenities
Non-smoking
No pets allowed
Family friendly
FAQs
Is parking included with this chalet?
Parking is not specified as an available 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 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.
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