Hilltop

With 360-degree views of the Catskill and Berkshire Mountains from the highest point in Hillsdale, Hilltop is a contemporary home with complete privacy and everything you need, including a pool, hot tub, fireplaces in the living room, screened porch and guest house.

Hilltop is between the towns of Great Barrington and Hudson, Catamount Ski Resort is within 10 min, and there are many options for hikes, biking and leaf peeping.

As you approach Hilltop, panoramic views of rolling hills and lush greenery greet you from every angle, setting the stage for an unforgettable retreat.



Step inside and discover a light-filled sanctuary where tall ceilings and thoughtful design elements create an atmosphere of effortless elegance and comfort. The main house welcomes you with an open floor plan seamlessly connecting the modern kitchen, dining, and living areas. Relax and unwind in the living room by the fireplace with direct access to the pool deck, where endless summer days await. Whip up gourmet meals in the fully equipped kitchen and dine in style indoors, where another set of large doors opens onto the deck, providing seamless transitions between indoor and outdoor living. Just off the living room, there is a music room, with an ensuite office space.



Two guest bedrooms offer full-sized beds, and there is a full guest bathroom for everyone's convenience. Ascend to the second floor, where the entire level is dedicated to the primary suite—the epitome of comfort boasting awe-inspiring views with a king bed, a spacious bathroom with soaking tub and separate shower, and a walk-in closet.



Step outside to Hilltop's sprawling grounds, where endless outdoor enjoyment awaits amidst spectacular views and breathtaking sunsets. The courtyard oasis features a pool, a hot tub, outdoor dining and lounging and an outdoor shower. Off of the patio, a screened in porch complete with its own fireplace is perfect for cozy evenings. With Catamount Ski Resort just minutes away and a variety of hiking, biking, and leaf-peeping options nearby, Hilltop is the perfect destination for outdoor enthusiasts and nature lovers alike.



South of the main house, the charming guest house offers a private haven with a kitchenette, living area, wood-burning stove, full bath, and bedroom, along with a private deck, perfect for unwinding amidst the natural beauty. The bedroom has a queen bed and a full size sofa bed.



Escape to Hilltop and experience the epitome of comfortable country living, where every amenity and comfort awaits amidst breathtaking natural beauty. This is more than just a home; it's a lifestyle of unparalleled comfort and tranquility.

A/C: There are two thermostats that control the air conditioning—one in the master bedroom, which cools that room and the bedroom below it, and another in the music room/bedroom, which cools that space. The living room, dining room, and kitchen are not separately air conditioned; to help cool these areas, you can use a fan to circulate air from the adjacent cooled rooms.

Hilltop, the perfect respite from the outside world in it’s tranquil solitude. However, not far off is the charming town of Hillsdale NY, Great Barrington MA and Hudson NY. These towns all have great restaurants, shopping, yoga, breweries/distilleries and cultural and historical sites. Visit the house guide for more recommendations!

To enjoy the expansive beauty of the region, you'll need a car to get here and get around and the drive will be stunning! Since cell service can be inconsistent in the country, we recommend that you download the region's online maps to your phone before your trip. We strongly advise using or renting a car that has all wheel or 4 wheel drive to access the property in winter.

We provide electronic access to the house with a personal guest code. You'll receive the code 24 hours prior to checkin, though your code will only activate at check-in.