Hillside Haven

Book your summer getaway in the Berkshires now!

Hillside Haven is a contemporary and spacious family retreat, with 4 bedrooms and 3.5 bathrooms, elevated furnishings and finishes in the woods near Great Barrington and Hillsdale. Whether you’re here with family or friends, for vacation or a work getaway, you’ll find everything you need! Enjoy a large terrace with outdoor dining and grill, sunroom office, convenient workstations, and a bonus meditation or yoga room.

Approaching Hillside Haven, you're greeted by the tranquil ambiance of its prime location near Great Barrington and Hillsdale. As you step inside this 3,500-square-foot home, you're immediately captivated by contemporary elegance and the natural serenity of the surroundings.



The heart of this home is the open-plan great room, where large windows flood the space with natural light and two large sliding doors open seamlessly to the outdoor deck. Step through the glass doors and discover the perfect setting for alfresco dining, complete with a professional-grade gas grill.



The bright and fully equipped kitchen boasts modern appliances and fine finishes, a large kitchen island,. Adjacent to the kitchen, the formal dining room, separated by columned archway, is perfect for intimate dinners. A sunroom off the kitchen offers a wonderful light-filled office. 



Retreat to the main floor primary bedroom oasis featuring a king bed and a spa-like en-suite bath. A private study with a pull-out sofa and a screened porch provide additional spaces privacy and convenience. Upstairs, a second primary suite awaits with its own king bed, en-suite bath and a convenient work space, while two guest rooms provide two queen beds, and one king bed. A large bonus room offers the perfect space for a quiet meditation or yoga session.



We’ve thought of everything to make your stay as comfortable and enjoyable as possible. Central air and heat, SONOS speakers, and large smart TVs in the family room and master suite ensure comfort and entertainment for everyone. The fully equipped kitchen includes a coffee maker, grinder, full set of pots and pans, plates, cutlery, and basic kitchen equipment. Fresh linens, fluffy towels, and toiletries are all provided to make packing a breeze.



Hillside Haven is the perfect escape for your next vacation boasting style, comfort and breathtaking natural beauty in a prime location. Let Hillside Haven be your gateway to an unforgettable Berkshire escape!

The house is nestled into a tranquil, wooded hill in Egremont, on the border of Hillsdale (NY) and Great Barrington (MA). In summer, slide into your flip-flops and take a short drive to Prospect (5 minutes) for a swim, enjoy the waterfall at the end of a gentle hike at Bash Bish Falls, or enjoy summer activities at Catamount Mountain Resort. In winter, you can reach the ski slopes in 5 minutes at Catamount, a favorite for families interested in skiing and snow tubing. In the fall, the hundreds of maple trees on the property blaze bright red in a wondrous display of leafy autumn magic.



Enjoy shopping and dining in Hillsdale or Great Barrington, or the outstanding cultural offerings, parks, and fine food in the southern Berkshires region. We provide plenty of recommendations in our house guide.

Hillside Haven is approx. 2.5 hours from Boston and just under 3 hours from New York City. You'll definitely need a car to get here and get around. The house has moderate cell service with AT&T and T-Mobile, but the Berkshires are full of cellular dead zones, so you may want to download the region's online maps to your device prior to your arrival or any day tripping you do while you’re here.

Guests have the entire 2-acre property for their private use.