Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style
9.9 / 10
Outstanding(108 Ratings)
$$$$
Chalet in Hillsdale, NY
6 guests · 2 bedrooms · 1 bath
Reasons to book
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
Location
Reviews
10 / 10
Property is as it appears a great location. Quiet but convenient to everything. Host is great & always accessible. I have stayed in the house 3 times & have not been disappointed.
10 / 10
Came for a family wedding. Had a great time enjoying lots of activities in the area-Bash Bish falls, Norman Rockwell Museum, Jacobs Pillow and Mac Haydn Theatre. Would highly recommend!
10 / 10
This is just a great vacation house, especially for a family! Very nice, clean, beautiful property, hosts are lovely. Don't hesitate!
10 / 10
Had a wonderful stay. The house was warm and cozy. The hosts were super friendly and accommodating. Location is perfect for a stay in Hillsdale.
Property is as it appears a great location. Quiet but convenient to everything. Host is great & always accessible. I have stayed in the house 3 times & have not been disappointed.
10 / 10Outstanding·Jun 2026
Came for a family wedding. Had a great time enjoying lots of activities in the area-Bash Bish falls, Norman Rockwell Museum, Jacobs Pillow and Mac Haydn Theatre. Would highly recommend!
10 / 10Outstanding·May 2026
This is just a great vacation house, especially for a family! Very nice, clean, beautiful property, hosts are lovely. Don't hesitate!
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
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
Free Parking
Air conditioning
Non-smoking
TV
Heating
Coffee/tea maker
Refrigerator
Kitchen
Balcony/Terrace
WiFi/Internet
Parking Available
Microwave
Dishwasher
Washing machine
Dryer
Washer/dryer
Kitchenware
No pets allowed
Ski in/Ski out
Garden
Oven
Stove
Laundry services
Bath or shower
Family friendly
Towels
Linens
Hairdryer
Fire extinguisher
FAQs
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 29 amenities for this rental. This includes free parking, air conditioning, non-smoking, tv, and heating.
Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style
Top rated by guests
9.9Outstanding
(108 Ratings)
"Property is as it appears a great location. Quiet but convenient to everything. Host is great & always accessible. I have stayed in the house 3 times & have not been disappointed."
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
Free Parking
Air conditioning
Non-smoking
TV
Heating
Coffee/tea maker
Refrigerator
Kitchen
Balcony/Terrace
WiFi/Internet
Parking Available
Microwave
Dishwasher
Washing machine
Dryer
Washer/dryer
Kitchenware
No pets allowed
Ski in/Ski out
Garden
Oven
Stove
Laundry services
Bath or shower
Family friendly
Towels
Linens
Hairdryer
Fire extinguisher
Map of Hillsdale, NY
Ratings and reviews
9.9 / 10
Outstanding(108 Ratings)
10 / 10Outstanding·Jul 2026
Property is as it appears a great location. Quiet but convenient to everything. Host is great & always accessible. I have stayed in the house 3 times & have not been disappointed.
10 / 10Outstanding·Jun 2026
Came for a family wedding. Had a great time enjoying lots of activities in the area-Bash Bish falls, Norman Rockwell Museum, Jacobs Pillow and Mac Haydn Theatre. Would highly recommend!
10 / 10Outstanding·May 2026
This is just a great vacation house, especially for a family! Very nice, clean, beautiful property, hosts are lovely. Don't hesitate!
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
(108 Ratings)
"Property is as it appears a great location. Quiet but convenient to everything. Host is great & always accessible. I have stayed in the house 3 times & have not been disappointed."
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
Map of Hillsdale, NY
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
Free Parking
Air conditioning
Non-smoking
TV
Heating
Coffee/tea maker
Refrigerator
Kitchen
Balcony/Terrace
WiFi/Internet
Parking Available
Microwave
Dishwasher
Washing machine
Dryer
Washer/dryer
Kitchenware
No pets allowed
Ski in/Ski out
Garden
Oven
Stove
Laundry services
Bath or shower
Family friendly
Towels
Linens
Hairdryer
Fire extinguisher
FAQs
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 29 amenities for this rental. This includes free parking, air conditioning, non-smoking, tv, and heating.
Looking to create some memories in Hillsdale? Look no further than our Apartment, Hillsdale House, 3BR/2.5BA – 5 Min to Catamount. Enjoy top-rated amenities including ;, and more.
Discover the beauty of Hillsdale with a stay at Hillsdale House, 3BR/2.5BA – 5 Min to Catamount, a top rated Apartment with amenities such as ;, and more.
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, Outdoor Cooking and Cribs or cots available, and more.
Experience vacation in Hillsdale with our House, Bellwether on Main: Comfort, Resilience, Passive House; an AAC building. Enjoy amenities such as Air conditioning, Dryer and Free Parking, 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 Free Parking, and more.