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 wooden deck with a table and chairs.
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.

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.

Popular amenities

  • Balcony
  • Air-conditioning
  • Refrigerator
  • Internet
  • Washing machine
  • Onsite parking available

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, Hudson, NY (HCC-Columbia County)
    ‪27 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

Add dates for prices

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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 cycling and hiking/biking trails.
View more Chalets in HillsdaleOpens in a new window
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
  • Catamount Aerial Adventure Park - 4 min drive - 5.4 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
  • ‪Mom's Country Cafe - ‬10 min drive
  • ‪Dad's Copake Diner - ‬8 min drive
  • ‪Martindale Chief Diner - ‬9 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 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).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 104 out of 110 reviews
Rating 8 - Good. 5 out of 110 reviews
Rating 6 - Okay. 1 out of 110 reviews
Rating 4 - Poor. 0 out of 110 reviews
Rating 2 - Terrible. 0 out of 110 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property and an absolutely lovely stay! Great location, and Anita and Dan were great hosts. Would absolutely recommend and stay again!
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was our 5th time there and it was great as alwaysLove the place
Stayed 3 nights in Oct 2026
Verified review

8/10 Good

Liked: Check-in, communication, location, listing accuracy
The location was perfect for our weekend trip back ‘home’ for our 50th high school reunion.The house was well-stocked and the indoor and outdoor gathering spaces were inviting.
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This summer was the third or maybe fourth time we have stayed at this property and we were there for about two months. So we obviously enjoy it. The house is clean and well maintained, and is just the right size for another couple or kids to stay with us. There is a nice second-story outside deck that is perfect for grilling and just hanging out. The house is close to several restaurants, a grocery store and a wine shop.Since we were there for two months we also got to know a couple of the neighbors, who are delightful.Tanglewood is fairly nearby as are many other attractions in addition to the Great Outdoors. Great swimming and kayaking close by,All in all a nice place in a nice location with nice people around.
Stayed 56 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is just a great vacation house, especially for a family! Very nice, clean, beautiful property, hosts are lovely. Don't hesitate!
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
4th time there It’s always great
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great trip
Stayed 6 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfectly clean and beautiful. We enjoyed everything about our stay. While enjoying privacy we were still a short walking distance to the charming town.
Stayed 4 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 3 nights in Jan 2026
Response from VrboOwner on 5 Jan 2026
Thank you for being such wonderful guests! Would love to have you again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location.

Great house & location. Host is a great communicator. Our second stay.
Stayed 4 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was very clean and well supplied with essentials. Hosts Daniel and Anita were very friendly and helpful. We would stay here again.
Stayed 3 nights in Aug 2025
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy

Easygoing little house

Clean, comfortable, welcoming. We enjoyed our stay.
Stayed 7 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Third stay

Very good location for us
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect getaway

Great house and beautiful property in a terrific location! Owners were gracious and easy. Would definitely stay again.
Stayed 4 nights in Jul 2021
Response from VrboOwner on 7 Jul 2021
Thank you! We would love to have you again!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Converted barn

Great location near everything. Host was always available for any questions. We enjoyed our stay.
Stayed 4 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Good spot close to Hillsdale

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.
Stayed 3 nights in Feb 2024
Response from VrboOwner on 22 Feb 2024
Thank you for being such wonderful guests. We would sure love to have you again.
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful place to stay!

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.
Stayed 4 nights in Aug 2023
Response from VrboOwner on 19 Aug 2023
Thank you for staying with us. We wish you had said something about the humidity. Each bedroom has an air conditioner with a de-humidifier option. We left the air conditioners on automatic and it was still like that when we came to clean after you left. It's just a matter of switching it over to the de- humidifier option if the humidity becomes too high for your taste.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fall stay in Hillsdale

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
Stayed 3 nights in Oct 2022
Response from VrboOwner on 17 Oct 2022
Thank you! We would sure love to have you back!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect getaway

The place was very clean and ready for us when we arrived. It was one of the nicest places we have every rented. For our weekend getaway with the family it as perfect. Definitely will consider a return visit!
Stayed 3 nights in May 2021
Response from VrboOwner on 31 May 2021
Thank you for staying with us. We would love to have you back!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

A lovely place to enjoy town and nature together

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.
Stayed 4 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great House

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
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderfull

Very nice, clean, stylish place. I would come back again.
Stayed 5 nights in Jan 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ms

Great stay for parent’s weekend
Stayed 3 nights in Oct 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic!

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.
Stayed 4 nights in Aug 2022
Response from VrboOwner on 6 Sept 2022
We would sure love to have you back!
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