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

Hillsdale, New York
$224 avg/night
Minimum Stay 3 Nights
Bed 2

Bed

Bath 1

Bath

Home Chalet

Property Type

Sleep 6

Max Sleeps

Night 3 nights

Min Stay

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.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • SKI

    Close To Skiing
  • PETS

    No Pets Allowed
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 1200 Sq Ft (112 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Paper Towels Refrigerator Spices Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Required Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Balcony Garden
  • BATHROOMS

    1 Bathroom Bathtub Or Shower Hair Dryer Toilet Paper Towels Provided
  • LANGS SPOKEN

    English French German
  • THINGS TO DO

    Cycling Nearby Golf Nearby Hiking Nearby Hiking/biking Trails Nearby Swimming Nearby
  • ENTERTAINMENT

    Games TV
  • LIVING SPACES

    Dining Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Games
  • LOCATION HIGHLIGHTS

    In A Village Near A Health Or Beauty Spa
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Availability

Review Review

  • Paul L.

    Submitted Feb 20, 2026

    Stayed Feb 14, 2026

    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.

  • Armando T.

    Submitted Jan 5, 2026

    Stayed Jan 1, 2026

    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!

  • Leah V.

    Submitted Oct 24, 2025

    Stayed Oct 17, 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.

  • Randy O.

    Submitted Oct 13, 2025

    Stayed Oct 9, 2025

    4th time there It’s always great

  • Jonathan K.

    Submitted Aug 30, 2025

    Stayed Aug 24, 2025

    Great trip

  • Aurora C.

    Submitted Aug 24, 2025

    Stayed Aug 20, 2025

    We had a beautiful stay at this historic, converted barn home on a super quiet street very centrally located just off the center of town. It was a great size for our family of 5 (children aged 2-7), well furnished and comfortable, clean and ample space to run outside. We had very pleasant breakfasts on the balcony overlooking a mountain shaded by big oaks and maples. Had great fast communication with the owners who were generous to allow an early check-in and provide us with some items we requested. And 10-15min drives to nearby kid-appropriate hikes! Highly recommend

  • Michael S.

    Submitted Aug 11, 2025

    Stayed Aug 6, 2025

    House was very clean and well supplied with essentials. Hosts Daniel and Anita were very friendly and helpful. We would stay here again.

  • Scott T.

    Submitted Aug 5, 2025

    Stayed Jul 24, 2025

    The carriage house in Hillsdale was a perfect spot to stay. My wife and I and our adult son stayed for a few days. We came to do some hiking in the Berkshires. The location was great. We planned to do cook dinners. The kitchen would have been more than adequate for this but we ended up eating out most meals as the local restaurant was quite tasty. We had a very minor issue with the house and Dan and Anita were very responsive.

  • Gail M.

    Submitted Jul 6, 2025

    Stayed Jul 2, 2025

    Great house & location. Host is a great communicator. Our second stay.

  • Barbara Z.

    Submitted Jan 24, 2025

    Stayed Jan 17, 2025

    We stayed in this converted carriage house and overall had a nice time. The space was mostly clean, though we did notice some dust in a few areas and quite a few bug traps around the house, which could be concerning. Being in an older home, it’s important to note that there were settling noises at night, which is to be expected. On the positive side, the hosts were very kind and responsive, especially when our daughter wasn’t feeling well. They went out of their way to help us get a thermometer, which was tricky to find locally since Hillsdale doesn’t have a nearby pharmacy. Despite the few concerns, the hospitality made our stay memorable.

  • Gilda G.

    Submitted Nov 6, 2024

    Stayed Oct 15, 2024

    Clean, comfortable, welcoming. We enjoyed our stay.

  • Randy O.

    Submitted Oct 14, 2024

    Stayed Oct 10, 2024

    Very good location for us

  • Sandy A.

    Submitted Oct 9, 2024

    Stayed Oct 4, 2024

    This converted barn was great for our needs because it was spacious for our get together with nearby family. The outdoor space was great for the kids. There was ample cooking supplies and linens

  • Chris D.

    Submitted Sep 11, 2024

    Stayed Aug 23, 2024

    We stayed in this house in the summer of 2023 and again in the summer of 2024- actually for two different stays in 2024. The house has a great location - you can walk to a couple of restaurants, the grocery store and the wine shop. By “walk” I mean a block or two. But being in Hillsdale, it is located on a large lot, with plenty of privacy and parking. It is close to several State parks: Copake, Taghkanic, Rudd Pond and Guilder Pond. Plus golf, biking and hiking trails. The Berkshires are close. The house has good Wi-Fi, a second-floor porch, a nice electric grill. Two bedrooms. The host is super-responsive by text and very accommodating. Very clean and everything works.

  • Flora S.

    Submitted Jul 25, 2024

    Stayed Jul 16, 2024

    The house was clean and quaint and the property is on a nice quiet street. The owners were super quick responding to our texts and answered the phone a couple of times the first day for questions on the tv/internet. We appreciated that they notified us when they came up to stay in their main house over the weekend. The location is exceptional, close to the Berkshires, Kripalu, Hudson and state parks. It's an easy walk to the town, which has a good supermarket, a liquor store, coffee shop, gift shops and a bar/restaurant (Hillsdale house). We cooked dinner in the house most nights with no issues. We met Dan, the owner, who is nice and laid back. A fabulous getaway for the week and will likely look to book again.

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Total

Includes taxes and fees
$253+
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