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

10.0 (106 Reviews) |   2 Bedrooms  1 Bathroom  6 Guests
Hillsdale Ski Chalet | Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style

2 Bedroom Ski Chalet with Air Conditioner, Parking and TV

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.

Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style is located in Hillsdale. Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style provides accommodation, featuring Air Conditioner, Parking, TV, among other amenities. This Ski Chalet features Air Conditioner, Parking, TV, to make your stay a comfortable one.

Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style has 2 Bedrooms , 1 Bathroom, and max occupancy of 6 persons. The minimum rental for this property is 1 night, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Ski Chalet because of the excellent services rendered by the owner or manager of this Ski Chalet, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Ski Chalet has a friendly neighborhood, and the Hillsdale has interesting places to visit. If you want to learn more about the Ski Chalet in Hillsdale, such as places to visit and things to do nearby, you can check below to learn more.

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Hillsdale, 12529, USA

Amenities

Air ConditionerAir Conditioner
ParkingParking
TVTV
Balcony/TerraceBalcony/Terrace
Security/SafetySecurity/Safety
Sports/ActivitiesSports/Activities
Bedding/LinensBedding/Linens
Wellness FacilitiesWellness Facilities
Fireplace/HeatingFireplace/Heating
EntertainmentEntertainment
Child FriendlyChild Friendly
InternetInternet
KitchenKitchen
LaundryLaundry

Facility Overview

Air ConditionerAir Conditioner
  • HeatingHeating
  • Air conditioningAir conditioning
BathroomsBathrooms
  • Hair dryerHair dryer
  • 1 bathroom1 bathroom
  • Towels providedTowels provided
  • Toilet paperToilet paper
  • Bathtub or showerBathtub or shower
BedroomBedroom
  • 2 bedrooms2 bedrooms
  • Bed sheets providedBed sheets provided
  • Dining roomDining room
KitchenKitchen
  • Coffee/tea makerCoffee/tea maker
  • Paper towelsPaper towels
  • DishwasherDishwasher
  • Cookware/dishes/utensilsCookware/dishes/utensils
  • MicrowaveMicrowave
  • StovetopStovetop
  • OvenOven
  • RefrigeratorRefrigerator
  • SpicesSpices
LaundryLaundry
  • Laundry facilitiesLaundry facilities
  • Washing machine and dryerWashing machine and dryer
ParkingParking
  • Onsite parkingOnsite parking
  • Car requiredCar required
Pet FriendlyPet Friendly
  • No pets allowedNo pets allowed
AccessibilityAccessibility
  • Smoke-free propertySmoke-free property
ActivitiesActivities
  • Hiking nearbyHiking nearby
  • Hiking/biking trails nearbyHiking/biking trails nearby
  • Cycling nearbyCycling nearby
  • Swimming nearbySwimming nearby
  • Golf nearbyGolf nearby
EntertainmentEntertainment
  • GamesGames
  • TVTV
GeneralGeneral
  • Unit size: 1200 sq ft (112 sq m)Unit size: 1200 sq ft (112 sq m)
  • GermanGerman
  • FrenchFrench
  • EnglishEnglish
  • In a villageIn a village
  • Near a health or beauty spaNear a health or beauty spa
Guest ServicesGuest Services
  • Children's gamesChildren's games
InternetInternet
  • WiFi availableWiFi available
OutdoorsOutdoors
  • BalconyBalcony
  • GardenGarden
Security/SafetySecurity/Safety
  • Smoke detector installed (host has indicated there is a smoke detector on the property)Smoke detector installed (host has indicated there is a smoke detector on the property)
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Fire extinguisherFire extinguisher
  • First aid kitFirst aid kit
  • Deadbolt lockDeadbolt lock
SkiingSkiing
  • Close to skiingClose to skiing

Policies

Check-in
Check-in
Check-in time starts at 4:00 pm contactless check-in available
Check-out
Check-out
Check-out before 11:00 am contactless check-out available
Child Policy
Child Policy
Children are welcome.
Event Policy
Event Policy
No events allowed
Pet Policy
Pet Policy
Pets not allowed
Smoking Policy
Smoking Policy
Smoking is not permitted
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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

Reviews

Paul L.
Feb 21, 2026 01:33:16 AM
Review Score:   10
Summary: 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.
See All Reviews

FAQ's

Is this Hillsdale ski chalet pet-friendly for guests? 

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Hillsdale ski chalet have a swimming pool? 

No, this Hillsdale ski chalet does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Hillsdale ski chalet? 

Best-rates for the Hillsdale ski chalet starts from $254 per night with includes Air Conditioner, Parking, TV, Balcony/Terrace, Security/Safety, Sports/Activities, Bedding/Linens, Wellness Facilities, Fireplace/Heating, Entertainment, Child Friendly, Internet, Kitchen, Laundry with all other facilities. Casai.nz matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

Is Hillsdale ski chalet a family-friendly place to stay? 

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this ski chalet good or guests have recommended them suitable for families. As reported by the owner or manager, the ski chalet has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Hillsdale ski chalet wheelchair accessible or offer services for disabled guests? 

Based on the information received from our partner, the Hillsdale ski chalet has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Hillsdale ski chalet? 

Based on the information reported by the owner or manager, the Hillsdale ski chalet indicates 1 day stay policy at this ski chalet. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Hillsdale ski chalet? 

Based on the information reported by the owner or manager, details for the cancellation policy for the Hillsdale ski chalet are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

Check Ski Chalet Availability
Nightly rates from:
US $254
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