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
Let Us Find You The Perfect Home!
What Guests Are Saying
We really enjoyed our stay in this beautiful private house!
We stayed here for a ski week as two families
Great home, clean, well stocked with everything you need.
Great Place – great house- we had a wonderful time
We really enjoyed our stay in this beautiful private house!
We stayed here for a ski week as two families
Great home, clean, well stocked with everything you need.
Great Place – great house- we had a wonderful time
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 turnoverโdue to excessive mess or incidents involving bodily fluids such as blood, vomit, or wasteโa $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 donโt charge extra for additional guests up to the homeโs 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
Want to plan further ahead? Join our membership program to unlock the ability to request stays beyond our standard booking dates.
Beautiful home, very responsive and communicative host. The views were
Gorgeous property! Exceeded all our expectations. We hope to be
Pros:- Modern and eccentric design- Bright and airy space, lots
- Modern and eccentric design
- Bright and airy space, lots of sun in the morning
- Generous with supplies (bathroom necessities, an extra tank for the grill, 24H heated pool, laundry supplies)
- Fully equipped kitchen
- Upstairs bedroom and bathroom has an amazing view of mountain tops
- Plenty of outdoor areas to lounge
- Pool can be covered and uncovered with a flick of a switch
- Responsive host
Cons:
- Needs a little bit of organizing/tlc (silverware, laundry room, huge collection of CDโs and DVDโs, pantry)
- Challenging drive to the property, especially at night
- Downstairs bathroom locks were not working
- Upstairs bathroom does not have a lock
This is my 2nd RedCottage booking and they donโt disappoint. Very responsive and courteous staff. Will definitely book again โบ๏ธ
Beautiful setting, very privaste and tranquil. Very nice house with
Red Cottage and the local caretaker were friendly and professional and helped out when needed for any minor issues.
Wonderful 2 weeks. Situated between Great Barrington and Hudson so
A beautiful modern house with very unique design elements and
Beautiful house! Spotless. Very well managed and maintained. Would love
Great!
What a beautiful house! We loved staying there!
Great home, clean, well stocked with everything you need.
Architecturally stunning home. Great space for our group to spend
The views were stunning! We had a great stay at
Beautiful house, love the design and interior of the house
We stayed here for a ski week as two families
Our stay at Hilltop was lovely - the house was
Lovely place in a lovely town! Thank you for a
Beautiful place, views, house, land, decorโฆ. Peaceful, quiet, at the
Fantastic property, location, and host for a getaway! As my
Great Place - great house- we had a wonderful time
Wow! What a stunner of a property. My husband and
We had a lovely, relaxing stay at Hilltop. The home
Un lugar mรกgico, una casa rica en arquitectura , cada
My stay at hilltop was a truly incredible experience. The
Inside, the home was beautifully designed and spacious. We had everything we needed for a comfortable stay - including lavender scented toiletries). the rental service Posto was very responsive and the check in and out process was seamless - One tip I would mention is to not drive there at night as the mountain roads can be tricky! Overall, it was a fantastic stay and I would highly recommend this Airbnb to others looking for a secluded, mountain getaway.
This is a beautiful property and place to relax !
My group had an amazing stay with Red Cottage! We
I couldn't have imagined a more perfect three weeks than
One of the best experiences I ever had! Recommended!
Beautiful house on a very private hilltop. Lovely pool and
We love this place. Beautiful pool, gorgeous property. Itโs a
Beautiful panoramic private getaway recommended for a beautiful peaceful relaxation
My wife and I had a magical time in this
We had a wonderful stay! The place was clean and
Spent a weekend at Hilltop midwinter and had a wonderful
Unique stay, awesome house, very well equipped, would gladly visit
We really enjoyed our stay in this beautiful private house!
My fiancรฉ and I celebrated our engagement at the Hilltop
This house was spectacular! The setting was gorgeous and the
We had a fantastic stay at Hilltop, the privacy was
We had the most wonderful stay. Having traveled from Rhode
Beautiful modern space with an abundance of large windows and
Beautiful home and views. Clean. Very responsive.
Beautiful property, accommodations were perfect. Great getaway for our family
Great house and great location. A little pricey but likely
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 suiteโthe 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 conditioningโone 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.