1 / 42

Hillside Haven - Modern Home near Great Barrington

House in Egremont, MA

10 guests·4 bedrooms·3 bathrooms
4.9 · 41 reviews

Why you'll love this stay

Outdoor Living

Outdoor Living

Dine al fresco on a spacious terrace with grill and views.

Entertainment & Amenities

Entertainment & Amenities

Work-friendly spaces with sunroom office and dedicated meditation room.

Location & Accessibility

Location & Accessibility

Ideal Berkshires location for family and friends seeking nature and relaxation.

Property details

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. Pets: Not allowed. Smoking: Not allowed. Events: Not allowed. Suitable for: children and infants. 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. 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. 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! Guests have the entire 2-acre property for their private use. Please make sure to remove boots when in the house. Any damage to the wood floors will need to be paid for. 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.

Sleeping arrangements

Bedroom 1

1 King Bed

Bedroom 2

2 Queen Beds

Bedroom 3

1 King Bed

Bedroom 4

1 King Bed

What’s included

  • Self check-in

    Self check-in

  • Parking

    Parking

  • Washer

    Washer

  • Dryer

    Dryer

  • Air conditioning

    Air conditioning

  • Heating

    Heating

  • Kitchen

    Kitchen

  • Wi-Fi

    Wi-Fi

Guest reviews

Star icon 4.9 | 41 reviews
5
4
3
2
1
B

Ben

Star Icon 0 0Star Icon 0 1Star Icon 0 2Star Icon 0 3Star Icon 0 4

July 2026

We had a wonderful summer stay with our family. The house is really comfortable and set up perfectly for a large family to cook, work and and spend time outdoors. Communication was great and speedy. We will be back for sure!

P

Peter

Star Icon 1 0Star Icon 1 1Star Icon 1 2Star Icon 1 3Star Icon 1 4

November 2025

This property is a real gem - very generous spaces and room. Every aspect was in very good working order. Great hosts: communicative and helpful. We held a family gathering of 15 people for dinner - of which 10 stayed for 4 nights. Everyone was impressed with the property. Excellent nearby food shopping in Great Barrington. Our experience was very positive and would recommend to others looking for a similar large scale gathering.

T

Tasha

Star Icon 2 0Star Icon 2 1Star Icon 2 2Star Icon 2 3Star Icon 2 4

October 2025

⭐️⭐️⭐️⭐️⭐️ Premium Luxe Experience! We booked the Red Cottage for our women’s retreat in October 2025, and it was absolutely perfect! This property truly exceeded our expectations — beautifully designed, spotless, and incredibly comfortable. Every detail felt thoughtfully curated, making our stay both relaxing and luxurious. The Red Cottage over-delivered in every way, and we can’t wait to visit again!

M

Molly

Star Icon 3 0Star Icon 3 1Star Icon 3 2Star Icon 3 3Star Icon 3 4

October 2025

A beautiful home perfect for a group trip! Spacious and roomy for everyone, and located in a wonderful stretch of the Berkshires. We had a lovely stay with a group of adults and are already hoping to come back in the summer.

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?

Site Footer

Get deals directly in your inbox:

© 2026 Whimstay, Inc. All Rights Reserved. “SEIZE THE STAY” and “WHIMSTAY” are registered trademarks of Whimstay, Inc. and the W Logo is a trademark of Whimstay, Inc.