Holiday houses in Butternut Basin

Walk Everywhere! | Relax in Easy Elegance!

Gracious in-town apartment feels like home: living and dining rooms, kitchen, 2 bedrooms, 2 baths—all just for you and your group. Walk to shops, restaurants, theaters, farmers’ market. Drive to more nearby arts offerings, hiking, skiing, swimming. Spectrum WiFi; please note, there is no TV. Bedrooms are small but with plenty of space to spread out, relax, read, play games or enjoy a meal in the entire apartment. The shared porch is available for morning coffee, evening cocktails or a good book.

Location · Family · Backyard

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

Family · Value · Decor

Berkshires Family Oasis with Hot Tub, Patio, Gym

All seasons family retreat in PRIME Berkshires location. Located adjacent to the famous Appalachian trail, 5 minutes from downtown Great Barrington, 2 minutes from Ski Butternut and 15 minutes from Tanglewood in Lenox. Easy access to sensational hiking, dining, lakes and museums. The home is spacious and open with 4 BR, 7 beds, a large finished basement TV & game room space and backyard patio and hot tub. A perfect spot to enjoy the spectacular beauty and unlimited activities of the Berkshires.

Location · Family · Comfort

Hilltop Ski and Sun Chalet with Hot Tub

Welcome to your Berkshires escape—a spacious 5-bedroom, 3.5-bath home that offers the best of both worlds: tranquil seclusion but close to downtown Great Barrington and charming Sheffield. The home’s location is a dream for outdoor enthusiasts, with Butternut and Catamount ski mountains just a short drive away. Rest and unwind in the hot tub after a wonderful day on the mountain. Whether you’re here to ski, hike, or simply relax, you’ll feel right at home in this idyllic Berkshires getaway.

Family · Value · Long stay

The River’s Whisper

Just a short stroll from downtown and East Mountain Hiking trails, this charming two-bedroom apartment offers the perfect mix of comfort, convenience, and small-town charm. The apartment features a fully equipped kitchen and comfy living area for relaxing. Step outside and you’re minutes away from coffee shops, restaurants, and the vibrant culture of of Great Barrington. This is your ideal home base for hiking, skiing, or simply soaking in the natural beauty of the Berkshires.

Family · Location · Getting around

King Bed, Wi-Fi, 2m Ski Resort

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. * 1.5 miles to Downtown * 1.3 miles to Mahaiwe Performing Arts Center * 44 miles to Albany International Airport *4.5 miles to Great Barrington Airport KEY FEATURES: *MCM Design * Plush King Sized Bed w/ high end Centium Satin Linens *High Speed Internet *55" Smart TV

Value · Family · Check-in

3-bedroom Berkshire bungalow on 2.5 peaceful acres

Modern farmhouse bungalow with private bridge and brook! Offering privacy as well as nearby nightlife, set upon 2.5 acres of beautiful Berkshire landscape but only 7 minutes to downtown Great Barrington and a short drive to Catamount and Butternut ski area. Mountains, waterfalls, countless hikes and bike routes, farmers' markets, coffee shops, breweries, Shakespeare and Co, Tanglewood, and world-class restaurants all come together in this quintessential New England community.

Family · Location · Long stay

Lovely house in the Berkshires

Enjoy fall in this stylish mid-century retreat as the Berkshires come alive with crisp air and vibrant foliage. Explore Great Barrington, Tanglewood, or the Appalachian Trail, then return home to relax in a peaceful setting. Hosting matters to me - I focus on details so you feel comfortable and happy. I maintain high standards of cleanliness, and my team prepares the home with care. Quality sheets and bedding ensure a comfortable stay.

Family · Value · Parks

Walk to Town! Great Barrington 4-bedroom farmhouse

Enjoy the yard and garden at this charming 4-bedroom in-town farmhouse. The garden features various fruits and vegetables in season. Stroll to Great Barrington's restaurants and shops. Hike the woodland trail up the hill for a swim at nearby Lake Mansfield. Retreat to the private garden hideaway. This place has something for everyone who wants to relax in a cozy setting yet still be near everything Great Barrington has to offer.

Family · Location · Outdoor spaces

Cottage on Scenic Road

NOTE!: As of Sept 2026 the wood stove is temporarily out of service and requires replacement. Please do not plan to be able to use the wood stove; I'll remove this note when the replacement is complete. One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf.

Family · Location · Laundry

Berkshires Black Abbey

Relax in a luxurious 4-person cedar sauna at the Berkshires Black Abbey, an 1862 church turned stunning 3-bed, 3-bath home in Mill River Village, MA. This 4,000 sq. ft. retreat blends original stained glass and vintage charm with modern comforts like heated floors, rainfall showers, a game loft with a speakeasy bar. Spacious deck, full kitchen, and room for up to 10 people

Family · Location · Hospitality

Prime location for the best of the Berkshires

Our warm and welcoming little house has been designed and outfitted to be highly accommodating and comfortable. Our country living location is private but also super convenient: just a mile from Butternut Basin Ski Resort; walking distance to the Appalachian Trail; an easy 5 minute drive to Main Street Great Barrington; and shopping for staples is likewise close by.

Family · Value · Wi-Fi