Hilltop
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Hillsdale
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House
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.
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Rooms and Beds
Features and Amenities
Rates and Availability
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What Guests Are Saying
Great!
We had a fantastic stay at Hilltop, the privacy was
This house was spectacular! The setting was gorgeous and the
Beautiful modern space with an abundance of large windows and
Great!
We had a fantastic stay at Hilltop, the privacy was
This house was spectacular! The setting was gorgeous and the
Beautiful modern space with an abundance of large windows and
Location
House Rules
Additional: VRBO: Guests must sign and return the rental agreement within 24 hours. If arriving tomorrow, complete the check-in form ASAP for instructions.
AGE REQUIREMENT
Primary guest booking must be 25 years or older. The person booking should also not have any negative reviews.
PETS
Sorry, pets are not permitted at this property.
SMOKING
No smoking is permitted inside the house. If you must smoke, please do so outside and dispose of butts properly. Any violation of this policy is subject to a $500 fee.
EXCESSIVE CLEANING FEES
We kindly ask that guests treat the home with care and respect. Should the property require cleaning beyond the standard turnover—due to excessive mess or incidents involving bodily fluids such as blood, vomit, or waste—a $500 fee may apply. Any linens or furnishings damaged beyond repair will also be subject to replacement charges. These situations are considered outside the scope of routine housekeeping and require specialized attention to ensure the safety and well-being of our team.
ACCURATE GUEST COUNT
The number of guests must be accurately disclosed at the time of booking. While we don’t charge extra for additional guests up to the home’s maximum occupancy, this information is essential so we can properly prepare and stock the home. Please note that penalties may apply if guest counts are inaccurate or intentionally misrepresented.
OUTSIDE SERVICE PROVIDERS
Outside staff such as private chefs, massage therapists, or other service providers are welcome, but prior approval is required before they come on-site.
SUPPLEMENTAL AGREEMENTS
Guests may be required to sign a rental agreement. If applicable, it will be sent after the booking is confirmed.
SEPTIC
Please be mindful of the septic system and do not flush anything down the toilets or drains other than toilet paper. This includes any and all personal hygiene products, baby wipes, bleaches and strong chemical cleaners.
Price Details
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Summary
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.
The Home
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.
Notes
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.
* Please note that the pool is available during the summer season only. Please inquire regarding opening and closing dates.