Great Barrington Vacation Rental Homes By Owner

Art and history meet breezy mountain adventures at this Great Barrington vacation rental! This 4-bedroom, 2-bathroom house boasts a private setting, the comforts... Read More

Summary: Your future home away from home in Great Barrington is a modern soup to nuts renovation on the footprint of an old house, combining the best of old and... Read More

Summary: Perfect Great Barrington house that is bright and airy with an open floor plan, the perfect spot for comfortable and communal gathering. Cozy, airy,... Read More

Summary: Easy & comfortable living on “The Hill” of Great Barrington. Our welcoming space has lots of personal touches, vaulted ceilings, open living space, and... Read More

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

PLEASE NOTE: WE ARE FULLY BOOKED FOR JULY & AUGUST 2021. And suddenly (or not!), summer 2020, the COVID summer, is over - and we are excited for the rest of '20... Read More

This updated home has a luxurious feel! Close proximity to downtown Great Barrington is convenient and allows for easy access to the world's cultural epicenter.... Read More

Lovely 4 bedroom, sleeps 10. 3-story classic Victorian home in family-friendly neighborhood. Clean modern interiors and nature-enjoying exteriors including... 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

Our antique farmhouse is minutes from town, hiking, and swimming. The large fenced in yard has a private pool, treehouse and apple and pear orchard and beautiful... Read More

Summary: You and your family cannot beat this PRIME location in downtown Great Barrington while still feeling remote and in the rolling hills of The Berkshires.... Read More

Just outside of downtown Great Barrington, this 1-bedroom, 1-bathroom, renovated barn-turned-cottage is ideal for a nature retreat! Explore the nearby hiking... Read More

New 3 BR rustic-yet-elegantly modern 2150 sq ft country castle on 3+ secluded acres in Manor Lane, part of a private compound off Hurlburt Road in Great... Read More

Summary: Just far enough outside of town to feel like you're getting away with all the conveniences of being a mile from great bars and restaurants, the Mahaiwe... 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

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

Charming turn of the century multi family apartment building. Newly renovated one bedroom ground floor apartment with bunk room. The apartment can... Read More

Located between the villages of Stockbridge, Housatonic and Great Barrington. Most unique Riverhouse property located on the bank of Rising Pond of the Housatonic... Read More

Summary: Newly renovated three bedroom “on the hill” in Great Barrington awaits your next family stay. Short walk to downtown Great Barrington for dining, easy... Read More

Charming turn of the century multi family apartment building. Newly renovated one bedroom apartment with the capacity to sleep 4. Including fully equipped... Read More