Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style
Top rated by guests
9.9Outstanding
(103 Ratings)
"Perfectly clean and beautiful. We enjoyed everything about our stay. While enjoying privacy we were still a short walking distance to the charming town."
Guests love it hereGuests give this property a top rating
Well priced for this locationPriced under area average
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
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
Perfectly clean and beautiful. We enjoyed everything about our stay. While enjoying privacy we were still a short walking distance to the charming town.
10.0 / 10.0Outstanding·Oct 2025
4th time there It’s always great
10.0 / 10.0Outstanding·Aug 2025
Great trip
5.0 / 10.0·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)
"Perfectly clean and beautiful. We enjoyed everything about our stay. While enjoying privacy we were still a short walking distance to the charming town."
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
Air conditioning
Non-smoking
TV
Coffee/tea maker
Refridgerator
Kitchen
Balcony/Terrace
WiFi/Internet
Microwave
Dishwasher
Washing machine
Dryer
Kitchenware
No pets allowed
Ski in/Ski out
Garden
Oven
Stove
Laundry services
Bath or shower
Towels
Hairdryer
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 22 amenities for this rental. This includes air conditioning, non-smoking, tv, coffee/tea maker, and refridgerator.
Experience vacation in Hillsdale with our House, Bellwether on Main: Comfort, Resilience, Passive House; an AAC building. Enjoy amenities such as Pets allowed, Family friendly and Non-smoking, and more.
Looking to create some memories in Hillsdale? Look no further than our Farm Stay, Private Unit in shared 1830 Farmhouse. Enjoy top-rated amenities including Air conditioning, Fireplace and WiFi/Internet, and more.
Discover the beauty of Hillsdale with a stay at The Brooks Motel, a top rated Motel with amenities such as Free WiFi/internet, WiFi/Internet and Air conditioning, and more.
Enjoy the best of Hillsdale in our House, Dreamy 6 Bedroom House, Come Enjoy Hillsdale!. A stunning property with amenities including Pets allowed, Family friendly and Non-smoking, and more.
WiFi/Internet · Air conditioning · Coffee/tea maker
Looking for a memorable stay in Hillsdale? Our Motel might just be what you're looking for. Enjoy amenities including Non-smoking, Air conditioning and WiFi/Internet, and more during your stay.
Looking for the perfect place to call home during your trip to Hillsdale? This House offers a comfort and style with top-notch amenities, including Air conditioning, Dryer and WiFi/Internet, and more.
Looking for a memorable stay in Hillsdale? Our House might just be what you're looking for. Enjoy amenities including Pets allowed, Family friendly and Non-smoking, and more during your stay.
Are you ready to indulge in a relaxing getaway? Our Apartment in Hillsdale has everything you need for a rejuvenating stay. Treat yourself to Brooks Motel: Perfect Suite, Seasonal Waterviews's exceptional amenities, such as Pets allowed and Family friendly.
Nestled in Hillsdale, this House is perfect for your next vacation. Enjoy The Brooks Buy Out, Wedding Groups Inquire Today!'s top-rated amenities, including Pets allowed and Family friendly, and more.
Experience vacation in Hillsdale with our House, Perfect House In Hillsdale, Brings Friends & Fam. Enjoy amenities such as Air conditioning, Fireplace and WiFi/Internet, and more.
Experience the best of Hillsdale with this Apartment available for $190. This property is equipped with amenities including Air conditioning, WiFi/Internet and Microwave, and more.
WiFi/Internet · Air conditioning · Coffee/tea maker
Looking for the perfect place to call home during your trip to Hillsdale? This Motel offers a comfort and style with top-notch amenities, including Non-smoking, Air conditioning and WiFi/Internet, and more.
Looking for the perfect place to call home during your trip to Hillsdale? This Apartment offers a comfort and style with top-notch amenities, including Air conditioning, WiFi/Internet and Microwave, and more.