Great Barrington: Vacation Rental By Owner

Nestled on the outskirts of Housatonic, a village in Great Barrington,MA. Country living at its best. Just minutes away from historic down town Great Barrington... Read More

This is a unique property located on more then 1000 feet of the Green River, one of the best Trout rivers in MA. Over a hundred and sixty acres of beautiful woods... Read More

This home is the perfect answer to fit your vacationing needs at any time of year. Ski, snowboard, snowshoe, or other outdoor activities in the Winter. Attend... Read More

This tranquil getaway is miles away from stress and hustle but just minutes' walk from the amazing shopping, dining and culture of Main Street Great Barrington.... Read More

There is only one cottage--30' away from our home--on this three-acre property. It has its own entrance and its own parking space. The pool is shared with us,... Read More

Leave your busy schedule behind for a life of leisure at this vacation rental hideaway. This 4-bedroom, 2-bath home is complete with woodsy-style decor,... Read More

NOW THROUGH MAY 10th 2020 - 2k/30 days!! Welcome to our Schoolhouse located in the heart of the Berkshires. Set in front of the ledges of Warner Mountain,... Read More

This 1000 square foot apartment offers a place for friends and family to spread out and make the stay comfortable. In the kitchen you will find an arrangement of... Read More

Renovated historic cape in the center of the quiet village of Housatonic. Five bedrooms, six beds, two full baths, private fenced backyard with hot tub and... Read More

The Cottage at Windflower Inn - close to skiing, shopping, hiking, and the arts. Located towards the back of the Windflower Inn property, our rental cottage... Read More

High-end, fully furnished, beautiful contemporary home on a private, four-acre, wooded estate next to Butternut Mountain. An open, three-level floorplan, tons of... Read More

Built in 2015, this lovely 4 bedroom, 2500 sq.ft. home on a knoll is set back 175 feet from the street. This charming home offers privacy and flexibility for... Read More

Enjoy our newly renovated haven (all new appliances, furniture, linens and towels) in the relaxing yet vibrant town of Great Barrington. We're just minutes from... Read More

7,500 SQ.FT. log cabin The perfect getaway on 10+ private acres. Once you're inside, you won't want to leave. CHECK IN SUPER EARLY AND CHECK OUT LATE - WE WANT... Read More

A short drive from New York City or Boston, or a flight into Hartford or Albany and you're in a new world of peacefulness - Gemini's Place in the Berkshires.... Read More

Situated on "The Hill" in Great Barrington, our beautiful modern Victorian home is just minutes from Main Street and Lake Mansfield. Our house is contemporary,... Read More

Located in the beautiful Berkshires, MA, the 5000 sqf home is located in a desired neighborhood known as "the Hill.” The sun filled house is on a quiet no outlet... Read More

This fabulous Timberframe Home has the best of all worlds for your family to enjoy time in the Berkshires. The panoramic views are breathtaking. A very private... Read More

This apartment is located in a renovated barn on a large private estate, centrally located in the heart of the Berkshires, on fifty acres of beautifully... Read More

Extraordinary privacy and convenience just a 10-minute walk to Main Street. You don't have to choose between privacy and convenience when staying at this grand... Read More