$9,750
Available: Right Now
Listed: 25/07/2024
Sheffield, MA, 01257
Our secluded property is a great place to relax and enjoy the company of your friends and family. The house has all the amenities: well-equipped kitchen, fireplace, sauna, Foosball and Ping-Pong tables, patio and an outdoor fire pit. Sheffield is a p...
$16,410
Available: Right Now
Listed: 22/07/2024
Sheffield, MA, 01257
I JUST purchased my dream house! I have been searching for a lake house in the Berkshires for years & when this came on the market I just had to say YES! It is a cozy newly renovated home situated on a 2 acre private peninsula surrounded on 3 sides b...
$15,960
Available: Right Now
Listed: 25/07/2024
Sheffield, MA, 01257
Hi! Welcome to the Berkshires! Enjoy total privacy on a full acre property overlooking 200 acres of conservation land. Warm nights by the fire & scenic views all in our fully stocked home 8 min from Great Barrington. Within literal steps of Sunset Me...
$15,570
Available: Right Now
Listed: 22/07/2024
Sheffield, MA, 01257
Your perfect country escape. Clean, spacious, light and airy home set in the middle of a meadow on 20 acres. Complete privacy, yet 10 minutes to downtown Great Barrington. Close to skiing at both Catamount and Butternut. There is room for everyone, w...
$21,630
Available: Right Now
Listed: 25/07/2024
Sheffield, MA, 01257
Undermountain Lodge offers an escape to a serene cabin, nestled between pristine natural spring lakes with panoramic mountain views, it comfortably accommodates up to 12 guests. Beyond the 6th guest, there's a $135 per person fee. Couples enjoy speci...
$16,890
Available: Right Now
Listed: 23/07/2024
Sheffield, MA, 01257
Family or couples getaway! 3 bedrooms plus library, Sleeps6-8 Abeautiful 3050 Sq. Ft., 2-Story Colonial and attached 2 car garage. Large, upscale chefs kitchen where everything is first class. Marble counters. Professional Blue Star (6 burner) gas ra...
$8,460
Available: Right Now
Listed: 25/07/2024
Egremont, MA, 01258
Cozy house conveniently located in a quiet area near the village of South Egremont. Fresh air, natures beauty all together close to Great Barrington and 2 ski resorts. This house is close to one of the most beautiful parts of the Appalachian Trail as...
$35,571
Available: Right Now
Listed: 21/07/2024
46 Bow Wow Rd, Massachusetts, 01230
Short term rental property, minimum 2 night stay (Listed rate is for full month and subject to change) The Freeman Berkshires sits on 40 acres of manicured landscape with a tennis court, a four-acre vineyard, a myriad of amenities and rolling views o...
$16,800
Available: Right Now
Listed: 25/07/2024
Egremont, MA, 01258
Shingled farmhouse with modern interior. Spacious & sunny kitchen that connects to the large outdoor patio with fireplace, living room with flat screen TV, first floor guest bedroom, laundry and full bath with tub. The second floor master suite has c...
$18,090
Available: Right Now
Listed: 25/07/2024
Sheffield, MA, 01257
Summary:Beautiful home with private yard and heated pool. Exquisite summer setting and breathtaking fall foliage in the town of Sheffield Massachusetts. Perfectly centered between Butternut and Catamount for winter activities!The Space:...
$17,760
Available: Right Now
Listed: 25/07/2024
Sheffield, MA, 01257
This rambling farmhouse has a balanced mix of meticulous restoration with an eccentric flair. Undermountain Farm is a home carefully designed with warmth and spirit. It also has a unique collection of fascinating antiques and collectibles.Enjoy c...
$9,510
Available: Right Now
Listed: 23/07/2024
Sheffield, MA, 01257
One of the very few waterfront homes available for rent. What other houses offer you 150 feet private lakefront where you can awake to birdsongThe absolute best house in the best little town for the full Berkshire experience. If you want your own tot...
$13,530
Available: Right Now
Listed: 25/07/2024
Sheffield, MA
Take a break from the city and relax at this charming Sheffield vacation rental in the Berkshires! The 3-bedroom, 2-bath house sits right on Mill Pond and boasts a retro interior, a Smart TV, a full kitchen, a dining room, an enclosed porch with seat...
$14,280
Available: Right Now
Listed: 25/07/2024
Sheffield, MA
Welcome to The Blue Elm - a cozy and historic Berkshire getaway located in Ashley Falls, MA.Set on 3.5 tranquil acres, the cottage ties into an early 19th century barn and is nestled amongst old growth maple trees.Enjoy this peaceful and conv...
$5,070
Available: Right Now
Listed: 25/07/2024
Sheffield, MA, 01257
Nestled in history and nature, The Historic Kellogg House, built in 1739, is the third oldest house in the Berkshires. Recently updated, the farmhouse seamlessly blends rich history with modern comforts, offering an exceptional retreat. Just 7 minute...
$15,120
Available: Right Now
Listed: 25/07/2024
Sheffield, MA, 01257
Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-...
$22,830
Available: Right Now
Listed: 21/07/2024
Sheffield, MA, 01257
Our home is a beautiful mountain-style home (exposed beams, wood floors, all new appliances) on a quiet rural road with commanding views of the Housatonic valley and Mt. Everett. Six miles to Great Barrington in the heart of the Berkshires. The house...
$8,640
Available: Right Now
Listed: 22/07/2024
Sheffield, MA, 01257
Bring friends or the whole family to this cozy accessible Berkshire County Country getaway. Only 5 minutes to Great Barrington! Close to Butternut and Catamount ski areas, Twin Lakes for boating, fishing, skiing, boarding etc., state parks, Tanglewoo...
$9,960
Available: Right Now
Listed: 25/07/2024
Egremont, MA, 01258
Situated on 26 acres in the heart of the Berkshires in the small town of South Egremont, MA, this early 19th c. house combines the charm of the antique with all the modern conveniences including two screened-in porches. Conveniently located five minu...
$42,480
Available: Right Now
Listed: 25/07/2024
Sheffield, MA, 01257
Historic fully updated brick house originally built in 1812 in the Berkshires in Western Massachusetts on one of the prettiest roads in the area. Minutes from Great Barrington and close to borders of Connecticut and New York, the spacious house sits ...
$28,890
Available: Right Now
Listed: 25/07/2024
Sheffield, MA, 01257
Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hours north of New York City, this circa-1770s center chimney colonial will charm and delight your family and guests. The rarest o...
$12,240
Available: Right Now
Listed: 25/07/2024
Sheffield, MA, 01222
Whether you’re chasing waterfalls on a hot summer’s day, hitting the slopes in the winter, or leaf-peeping in the fall, this all-season retreat is the perfect home base for enjoying the natural beauty of the Berkshires. Tucked on a private acre in th...