Hillsdale Rentals USA New York Hillsdale

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

10.0 (93 Reviews) |   2 Bedrooms  1 Bathroom  6 Guests  Stay&Play
Hillsdale Ski Chalet | Heart of Historic Hillsdale, NY, charming carriage house, Swiss Chalet-style

2 Bedroom Ski Chalet in Hillsdale

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 Bedding/Linens, Fireplace/Heating, Child Friendly, among other amenities. This Ski Chalet features Bedding/Linens, Fireplace/Heating, Child Friendly, 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 people. The minimum rental for this property is 1 nights, 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.

Show more
OneKey Logos

This Property is OneKey Eligible

Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.

JOIN TODAY

Unique Amenities

  • Air Conditioner
  • Parking
  • TV
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Wellness Facilities
  • Fireplace/Heating
  • Entertainment
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
Read More Read Less

Policies

Check-in Check-in time starts at 4:00 pm contactless check-in available
Check-out Check-out before 11:00 am contactless check-out available
Child Policy Children are welcome.
Pet Policy Pets not allowed
Other Policy 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
 
Hillsdale, 12529, United States

What Our Guests say 500 + Reviews

Jan 24, 2025 06:55:35 PM
Summary: 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.
Barbara Z. Barbara Z.
Nov 7, 2024 04:54:13 AM
Summary: Clean, comfortable, welcoming. We enjoyed our stay.
Gilda G. Gilda G.
Oct 14, 2024 09:34:09 PM
Summary: Very good location for us
Randy O. Randy O.
Oct 9, 2024 11:13:17 AM
Summary: 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
Sandy A. Sandy A.
Sep 11, 2024 08:33:53 AM
Summary: 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.
Chris D. Chris D.
Jul 26, 2024 05:00:21 AM
Summary: 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.
Flora S. Flora S.
Jul 7, 2024 08:39:41 AM
Summary: Great location near everything. Host was always available for any questions. We enjoyed our stay.
Gail M. Gail M.
Jun 8, 2024 12:00:57 AM
Summary: 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
Julie Z. Julie Z.
Apr 1, 2024 06:23:17 AM
Summary: So, this is 3rd time staying here. First 2 were for skiing catamount and butternut (they are very close). This time we did hiking, shopping and eating. This is a great centralized location between all the nice towns in NY and MA. There are tons of places to eat, hike and see within 10-30 mins any direction. The house itself is nice and clean, perfect for a family of 4. The owners are great, welcoming and friendly. We will def try to go back before next winter. Thanks again Dan!
Alissa S. Alissa S.
Feb 23, 2024 03:07:16 AM
Summary: 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.
David C. David C.

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 $194 per night with includes Internet, Laundry, TV, Security/Safety, Sports/Activities, Wellness Facilities, Entertainment, Kitchen, Air Conditioner, Parking, Balcony/Terrace, Bedding/Linens, Fireplace/Heating, Child Friendly StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

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.

People Also Ask

Check Ski Chalet Availability
Nightly rates from:
US $194
Price Details
You will be redirected to  
Hot Deal - It has been viewed 210 times today
Not the right fit? Check out our other properties in Hillsdale
|
8.8 (6 Reviews)
House
Tory Hill
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
view more places to stay

Recently Booked Locations

Recently Booked Properties