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The Camp - hiking trails right outside your door

Enjoy the peaceful silence, private forested expanses, wildlife, and unforgettable starry night skies from this wonderful home. Only 8 minutes to the village of Charlemont and 5 to the Tannery Falls entrance of the Savoy State Forest. During your escape on the mountain rest assured that you’re only a 30 minute drive to Norths Adams, Greenfield. Highlight your visit with journeys to Berkshire East Ski Resort, Thunder Mountain Biking, Zoar Outdoor River Rafting, MASS MoCA, or the Clark Art Museum.

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Rustic Secluded Cabin near Berkshires. *wood stove

The Red House offers a peaceful secluded retreat, surrounded by acres of forest & with excellent hiking trails. Enjoy the tranquility of nature while being minutes from antiquing, Kripalu, the Norman Rockwell Museum, The Mount, Tanglewood, skiing, & Shakespeare & Co. You'll appreciate the serene privacy, situated on an old dirt road. Relax by the wood stove or in the sunroom. Nearby towns of Spencertown, Chatham, & West Stockbridge offer unique charm. 4WD vehicle is recommended for winter visits

Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Price includes 1 king bedroom suite and exclusive use of the lounge and kitchenette. You can use 2 more suites for another $100 each per stay (for stays up to 2 weeks). Indicate the number of suites you will need (1, 2, or 3); you'll be charged for add'l suites later.

Quality, Comfort, Charm in Williamstown Center

Stay at this completely renovated house in the center of Williamstown! Conveniently located in a quiet neighborhood within easy walking distance to the town center, Williams College and The Clark Art Institute. The house was fully renovated in 2021. All new everything including appliances, a luxurious tile shower, fresh sheets and towels and lovely furnishings, all to make your stay comfortable and cozy. The living room has a beautiful gas fireplace and smart tv and in the summer, central air.

Bernie's & Betty's

Comfortably sleeping 6 with a large yard and screened-in porch, this charming 3-bedroom house is perfect for families looking for fun and adventure in the beautiful Berkshires. Minutes from Mass MoCA, Williamstown, and the Appalachian Trail, it is also an easy trip to Lenox (including Tanglewood) and other South Berkshire attractions. If you like the outdoors, you will love the easy access to ski slopes, hiking and biking trails. There is aTesla universal level 2 charger on the premises.

Modern, Renovated Lakefront Escape

Evergreen Home Vacation Rentals invites you to the East Beach Lakehouse, a stylish, recently renovated retreat on the shores of Richmond Pond. Situated on over an acre of land, this stunning property features a private dock and guest watercraft for the ultimate lakefront experience. Enjoy the heart of the Berkshires from the screened porch or host a BBQ on the grill. With ample space and modern amenities, it’s the perfect setting for relaxation and water adventures. Book your lake escape!

Charming Country House with a Hot Tub

Nested in the southern Berkshire County, this private house is perfect for all seasons. It's a 15 minute drive from Great Barrington as well as skiing, swimming lakes, trails and tons of nature. Set on a secluded 2-acre lot, the house offers ample outdoor space with a hot tub that runs all year, a firepit and out door dining area. The house features an open kitchen and dining area, a spacious and well-appointed living room with a gas fireplace, kids play area, a garage with EV charging.

Stunning luxury home with pool

Welcome to our weekend home in the Berkshires! We now rent it out when we’re not there, following a top-to-bottom renovation with all new furniture, and hope our guests enjoy it as much as we do. Our home is in Great Barrington, 2.5 hours' drive from NYC, surrounded by trees and parkland (Monument Mountain is next door). Yet it's less than 10-15 minutes' drive to town, shopping, restaurants, skiing, and Tanglewood. Come enjoy the Berkshires with complimentary gourmet coffee!

Friendly Hills | Passive Home • EV Charger

Welcome to Friendly Hills, a one-of-a-kind Mid-Century home nestled on 6 private acres. Built in the 1950s by GE engineer Willard F.M. Gray, this passive solar retreat offers panoramic views, triple-pane windows, and ceramic tile floors that retain heat year-round. Enjoy direct access to private hiking trails, peaceful ponds, and nearby Hancock Shaker Village. Fast Wi-Fi, thoughtful design, and natural beauty make this perfect for families, couples, and nature lovers alike.

Mountain View Victorian Retreat by Evergreen Home

Evergreen Home Vacation Rentals invites you to this beautifully restored Victorian, just a 5-minute walk to downtown. Located near MCLA and Mass MoCA, and 10 minutes from Williamstown, this spacious home offers stunning mountain views from the deck. Perfect for every season: enjoy Jiminy Peak skiing (30 mins), Vermont trails, or summer kayaking and fall foliage. Whether you’re here for art, culture, or a quiet retreat, this lovely home is your ideal Berkshire base.

The Cottage at The Barrington House

Welcome to the Cottage at the Barrington House! The Barrington House is nestled in the serene Berkshires Mountains - which have long been a sanctuary for weary city dwellers seeking breathing space, a perfect retreat for artists, writers and thinkers! It's sprawling grounds offer stunning views of lush valleys and distant peaks, while the interior features a fireplace, cozy reading nook, and unlimited windows that invite the natural world inside.