$6,900
Available: Right Now
Listed: 23/04/2024
Stockbridge, MA
Welcome to "The Hideaway On Main " in Stockbridge Center. Our recently renovated 2 bedroom unit offers a clean mix of modern elegance and cottage charm. With a private rear entrance and a charmingly modern ambiance full of delightful surprises, y...
$10,440
Available: Right Now
Listed: 19/04/2024
Stockbridge, MA
One of a kind must see getaway. Berkshire Glamour meets Hollywood Rennaisance and Town & Country. This well-lit, newly renovated designer home was built for entertaining, family vacations, romantic getaway, and/or an outing with friends and musicians...
$7,800
Available: Right Now
Listed: 23/04/2024
Stockbridge, MA
Old meets new in this lovely cottage, a short walk to the Red Lion Inn. Lots of light, comfortable furniture, beautiful, fenced-in backyard with mountain views. Kitchen updated with Smeg refrigerator, gas stove, granite counters, hardwood floors thro...
$6,360
Available: Right Now
Listed: 23/04/2024
Stockbridge, MA
Summary:Classic Southern Berkshire escape, built in the early 1900s by a cartographer for the NY Times. The home boasts a living room sized for entertaining, a separate library and an additional sitting space. The wood burning fireplaces in the l...
$5,700
Available: Right Now
Listed: 18/04/2024
Stockbridge, MA
This adorable wooden cottage feels bright, open, and spacious. It has modern amenities alongside its rustic charm. While it comfortably sleeps 2, there is ample room for a dinner party of 6. It sits on a south-facing hill, looking out towards Monumen...
$16,140
Available: Right Now
Listed: 23/04/2024
Stockbridge, MA
Absolutely stunning 2018 build less than 1 mile from downtown Stockbridge and an 8 minute drive to Ski Butternut and downtown Great Barrington. This 3 bedroom 3.5 bath is tucked away on a private road with one acre of peace and quiet. The grounds are...
$8,430
Available: Right Now
Listed: 23/04/2024
Stockbridge, MA, 01229
The Residence is a beautiful, secluded home in the Berkshire foothills. The 14-acre property includes hiking trails through the woods, a meadow, and a lovely babbling brook. Despite its secluded feel, the house just a short drive from many of the are...
$7,170
Available: Right Now
Listed: 22/04/2024
Stockbridge, MA
Unique small cottage in the sought-after Beachwood community situated 2 miles from Tanglewood on Stockbridge Bowl. Features open ceilings, skylights, 2 full bathrooms and large living room. Close to Kripalu, Lenox, Stockbridge, restaurants, hiking an...
$37,560
Available: Right Now
Listed: 23/04/2024
Stockbridge, MA
Available for the week of Labor day 2023. Completely reserved for June, July & August 2023. The estate is located a 5-minute drive from Stockbridge Village, 10 minutes to Tanglewood / Lenox, and less than 15 minutes to Great Barrington. This h...
$7,170
Available: Right Now
Listed: 22/04/2024
Stockbridge, MA
Cozy cabin located in the popular Beachwood community which is 2 miles from Tanglewood on Stockbridge Bowl, close to Kripalu, Lenox, Stockbridge, restaurants, hiking and everything else in the Berkshires. Large open yard, good size bedrooms and spaci...
$8,250
Available: Right Now
Listed: 18/04/2024
Stockbridge, MA
This bright and charming tri-level house is a stone's throw to Lenox, MA. With an open living area, the house has ultra high ceilings, skylights, and a Vermont Castings stove. Two main bedrooms are between the primary and top floor and share a bathro...
$29,970
Available: Right Now
Listed: 22/04/2024
Stockbridge, MA
The Taggart House is an grand estate in the heart of The Berkshires. The property is a 5-minute walk to the center of Stockbridge, yet quietly situated on 3 manicured acres along the Housatonic River. The Taggart House was constructed in 1850 by note...
$12,150
Available: Right Now
Listed: 18/04/2024
Stockbridge, MA
A classic Berkshire cabin nestled under maple trees, on the shore of the Stockbridge Bowl cove. Serene, peaceful and private, yet close to all area attractions. Private beach and dock. Swimming and kayaking. Large lawn with lots of trees. Newly renov...
$13,470
Available: Right Now
Listed: 22/04/2024
Stockbridge, MA
Summary:"Feels good staying here! We built this house with our own hands. We chose materials and a design that we loved and we think you will too! There are ash hardwood floors, custom white pine trim and mahogany decks. The interior has an open-...
$9,000
Available: Right Now
Listed: 22/04/2024
Stockbridge, MA
Transform yourself in to the middle of a Norman Rockwell painting. It is easy to see how so many of his paintings were inspired by homes like these and the Stockbridge locals. Cherry Hill at Farley's Crossing has been owned by the same family for ove...
$7,170
Available: Right Now
Listed: 23/04/2024
Stockbridge, MA
This charming Berkshires estate consists of a beautiful main house, an ample separate recreation space, and a private pool area. Welcome to Rockspring! located in Stockbridge, your group will be surrounded by all of the area's natural beauty while en...
$10,020
Available: Right Now
Listed: 22/04/2024
Stockbridge, MA
Blue House on the BendBuilt around 1820, the Blue House on the Bend, an historic eyebrow colonial located on an idyllic bend of the Housatonic river, has been updated and outfitted for modern day convenience but retains its charm and unique appea...
$17,700
Available: Right Now
Listed: 24/04/2024
Stockbridge, MA
In the heart of Stockbridge, Massachusetts, the rectory at St. Joseph's Church offers guests a truly divine retreat. This historic gem has been transformed into an exquisite short-term lodging, inviting you to experience a blend of timeless elegance ...
$10,500
Available: Right Now
Listed: 22/04/2024
Stockbridge, MA
Drive down our private road to find an adorable and spacious cottage, nestled on four secluded wooded acres, with every modern amenity including central air conditioning, Internet TV andWIFI.Added for2021 -Custom shed that serves as an office with di...
$9,480
Available: Right Now
Listed: 23/04/2024
Stockbridge, MA
Escape to the serene beauty of the Berkshires and stay at this bright and cozy 2-bed, 2-bath cabin! Nestled just a few steps from the Stockbridge Town Beach, the vacation rental is perfectly located for enjoying the area's top attractions, like lake ...
$10,230
Available: Right Now
Listed: 23/04/2024
Stockbridge, MA
Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house! Boasting a private deck, fireplace, in-unit laundry, and 114 acres of property to explore, this home-away-from-home can’t be beat! When you aren’t enjoy...
$18,390
Available: Right Now
Listed: 23/04/2024
Stockbridge, MA
This gorgeous farmhouse has four bedrooms each with a private full bathroom. Each bedroom has a queen size bed, sitting chair and closet or armoire .There is a fully stocked kitchen, living room with fireplace and dining room that seats 8 people. Thr...