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Berkshires Waterfront Retreat w/ Hot Tub & Kayaks

A peaceful waterfront retreat perfect for family gatherings or a friends’ getaway! This Berkshires home features 5 bedrooms, 3 bathrooms, and sleeps 10—set right at the water’s edge with total privacy. 🌸 Serene nature views & blooming spring scenery ☀️ Kayak & relax on the private waterfront 🔥 Firepit for summer nights 🛶 Kayaks & hot tub 🥾 Hiking, farms, towns & great local dining nearby 🔌 Level 2 EV charger ❄️ Winter Skiing fun Unwind, explore, and make lasting memories all season long!

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.

Luxury Glamping, Private, Wood Burning Hot Tub

Guests often say: "We felt like we had our own private forest." Welcome to Glamping in Hephzibah, a one of a kind luxury glamping retreat nestled on 23 private acres in the beautiful Berkshire Hills of Western Massachusetts. Unlike many glamping sites this is not a resort with multiple units sharing the same property. The entire experience is yours. No neighboring tents. No shared facilities. No strangers nearby. Just you, your family, and a private forest waiting to be explored.

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.

Hillside Haven

Ideally located on “the hill” in a beautiful and quiet neighborhood just a short walk to downtown Great Barrington’s amazing cafes, restaurants, ice cream, and Lake Mansfield’s beach and loop trail. The perfect hillside haven for those looking to be in the center of it all. This private, modern, and clean space is completely new as of mid-2021 and has a well-appointed kitchen, outdoor patio with a firepit, fast internet, covered parking, radiant heat floors, and an air conditioning unit.

Historic House on the Hill by Evergreen Home

Evergreen Home Vacation Rentals invites you to this spacious, recently renovated late 19th-century Victorian. Located within walking distance of downtown North Adams and Mass MoCA, this home is the perfect base for visiting MCLA or Williams College. Relax on the second-floor balcony or enjoy dinner on the deck under stylish café lights. Featuring 3 bedrooms, a full kitchen, and smart amenities, you are just 30 minutes from Jiminy Peak. Experience historic charm and modern comfort.

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.

Zen River Studio

This comfortable, newly renovated garden level studio has all you need for a relaxing get-away. The bright sunroom has an expansive view of East Mtn. & Housatonic River with a fully equipped efficiency kitchen perfect for making simple meals. Bathroom includes luxury steam shower & bidet. Fab King bed. Be far away from it all while being in the center of the Beautiful Berkshires; walk to town w/ restaurants, shops, hiking trails, cultural attractions and MORE.