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Hilltop: Panoramic Views w/ Pool near Catamount

House in Hillsdale, NY

8 guests·4 bedrooms·3 bathrooms
4.9 · 52 reviews

Why you'll love this stay

Outdoor Living

Outdoor Living

Soak in mountain views from a private pool and hot tub.

Location & Accessibility

Location & Accessibility

Prime Catskills foothill location near skiing, hiking, and leaf peeping.

Entertainment & Amenities

Entertainment & Amenities

Fireplaces, screened porch, and luxe interiors create resort-like relaxation.

Property details

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 that is included on your rental! 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. 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. Pets: Not allowed. Smoking: Not allowed. Events: Not allowed. Not suitable for children or infants. Reason: Not suitable for children.. Additional rules: AGE REQUIREMENT Primary guest booking must be 25 years or older. 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.. 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. MID-STAY CLEANING REQUIREMENT For stays of 28 nights or longer, a guest-paid mid-stay cleaning is required. The cleaning will be scheduled at a mutually convenient time during your stay. The cost varies by property and will be confirmed before scheduling. 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. 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. 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. 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! 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.

Sleeping arrangements

Bedroom 1

1 King Bed

Bedroom 2

1 Double Bed

Bedroom 3

1 Double Bed

Bedroom 4

1 Queen Bed

What’s included

  • Self check-in

    Self check-in

  • Parking

    Parking

  • Hot tub

    Hot tub

  • Pool

    Pool

  • Washer

    Washer

  • Dryer

    Dryer

  • Air conditioning

    Air conditioning

  • Heating

    Heating

Guest reviews

Star icon 4.9 | 52 reviews
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Mike

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October 2026

We had a beautiful stay. Amazing views and the house provided a layout that made for a great gathering of friends. It’s tucked away to ensure privacy but close enough to town and good coffee. Would certainly stay here again!

B

Blake

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September 2026

The house itself is nice with extraordinary views of the New York countryside. However, many things in the house are a bit outdated - we had problems closing several of the doors/windows and some of the lights did not work. With that said, we switched to this reservation after a last minute problem with our other Red Cottage booking (we were boarding the plane), and they were extremely responsive and helpful in getting us rebooked before we took off and also gave us a discount. Furthermore, they were willing to refund us a night because of some last-minute changes on our reservation. Overall, the house is nice but be prepared for some oddities, and the host was helpful in ensuring we had everything we needed!

J

Jeremy

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September 2026

We really enjoyed our stay. The property is beautiful and private, the architecture of the home is beautiful and wonderful to experience. The hosts were very responsible and helpful. We made full use of all the listed amenities and had a wonderful time. Would absolutely book again!

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Jason

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August 2026

Beautiful views. Had a lovely family get together.

Know before you go

Self check-in

House rules

Check-in: 4:00pm

Checkout: 11:00am

No pets allowed

Min. age to rent: 25

No smoking

No parties

Have a question about this property?

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