Chalet

Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style

Photo gallery for Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style

A two-story house with a balcony, surrounded by lush greenery and purple flowers.
A white two-story house with a balcony, a flag, and a mailbox.
A cozy loft-style apartment with a dining area, kitchen, and a balcony with a wooden railing.
A dining area with a table set for four, surrounded by wooden chairs. A microwave is on a shelf above the table, and a refrigerator is in the adjacent kitchen area.
A wooden deck with a table and chairs.

Reviews

10 out of 10
Exceptional

Highlights

  • Family fun awaits
    Top-rated for families.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
2 bedrooms1 bathroomSleeps 6

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Balcony
  • Internet access

Explore the area

View in a map
Hillsdale, NY
  • Place, Roe Jan Brewing Co.
    ‪7 min walk‬
  • Place, Hillsdale Town Hall
    ‪8 min walk‬
  • Place, Community Library
    ‪16 min walk‬
  • Airport, Pittsfield, MA (PSF-Pittsfield Municipal)
    ‪40 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

queen

1 Queen Bed

twin bedroom

2 Single Beds

1 bathroom

Bathroom

Bathtub or shower · Toilet

Spaces

Kitchen
Balcony
Separate dining area
Garden
Dining area

About this property

Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style

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.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
1) The key must be returned to the lockbox each time you leave the property 2) Shoes must be left in the solarium 3) Problems text 917-648-3657

Important information

You need to know

Property # 9312774
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Hillsdale

Hillsdale is home to this chalet. The area's natural beauty can be seen at Taconic State Park and Bash Bish Falls State Park, while Great Barrington Historical Society & Museum and Ancram Opera House are cultural highlights. Discover the area's water adventures with nearby swimming, or enjoy the great outdoors with hiking and cycling.
Map
Hillsdale, NY

What's nearby

  • Roe Jan Brewing Co. - 7 min walk - 0.6 km
  • Hillsdale Town Hall - 8 min walk - 0.7 km
  • Community Library - 16 min walk - 1.4 km
  • Tanglewood Music Center - 37 min drive - 51.4 km
  • Jiminy Peak Mountain Resort - 45 min drive - 71.6 km

Getting around

  • Hudson Station - 24 min drive
  • Hudson, NY (HCC-Columbia County) - 24 min drive

Restaurants

  • ‪Four Brothers Pizza Inn - ‬16 min walk
  • ‪Stewart's Shops - ‬3 min walk
  • ‪Martindale Chief Diner - ‬9 min drive
  • ‪Dad's Copake Diner - ‬8 min drive
  • ‪Mom's Country Cafe - ‬10 min drive

Frequently asked questions

Is Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style?

As of 21 Aug 2026, prices found for a 1-night stay for 2 adults at Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style on 18 Sept 2026 start from £560, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style?

On-site parking is available at the property.

What time is check-in at Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style?

Check-in begins at 4:00 PM.

What time is check-out at Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style?

Checkout is at 11:00 AM.

Where is Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style located?

Situated in Hillsdale, this chalet is within a 10-minute walk of Hillsdale Town Hall and Roe Jan Brewing Co.. Community Library and Catamount Aerial Adventure Park are also within 3 miles (5 km).

About the host

Hosted by Daniel Bodzin

Host profile image
We have been lucky to enjoy this property for the past 35 years.

Why they chose this property

This property is part of the historic district of Hillsdale. Our main house was built in 1827 and we tried to keep as much of the original look and charm of the barn as possible with exposed beams for instance. The property is in the center of town within walking distance of many amenities, yet it is private with 2.7 acres of land; a huge piece of land in the center of town.

What makes this property unique

Centrally located yet private. Cozy and historic.

Languages:

English, French, German

Premier Host

They consistently provide great experiences for their guests
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