- Massachusetts Lake House with Dock - Pets Welcome!New Marlborough
- Picturesque Cottage with Sunroom on Ashmere Lake!Hinsdale
- Shaker Mill Inn9.2West Stockbridge
- Berkshire Vacation Rentals 1900s Factory Turned Modern Berkshires RetreatGreat Barrington
- Cozy Monterey Home with Porch Walk to Lake GarfieldMonterey9.0
- Beautiful Two-Bedroom Cabin Rental Set in the Forests of the Berkshires, MassachusettsWorthington Center
- Walk to Ski Slopes Jiminy Peak Resort Getaway!Hancock
- Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4Hancock9.0
- Cozy Stockbridge Cabin - Walk to Beach and Lake!Stockbridge9.0
- Trail Access Berkshires Gem with Rooftop Deck!Lee
- Modern and Family-Friendly Vacation Rental in the Berkshires near Great BarringtonMonterey
- 2 BR JIMINY PEAK w Mountain Views SLEEPS 7 GorgeousHancock
- Imaginative Octogonal Glass Treehouse on Seven Private Acres near Great Barrington, MAOtis
- 1 Mi to Vineyard Serene Berkshires Country EscapeRichmond
- Cozy Berkshires Cabin with Lake, Beach, Hot Tub, Fireplace - The Wilde BNB
- Cozy Log Cabin with a Private Hot Tub near Beartown State Forest, MassachusettsMonterey
- Riverfront Cabin with Beautiful Views of Housatonic River in Great Barrington, Massachusetts
- Beautiful House in the Woods, Huge Yard, Hot TubGreat Barrington
- Watercrafts and Dock Stunning Lakehouse in Becket!Becket
- Lee ManorLee
- Pleasant Valley Motel West Stockbridge5.4West Stockbridge
- Four-Bedroom Luxury House Rental on Pontoosuc Lake in the BerkshiresLanesborough
- 2 Mi to Norman Rockwell Museum Stockbridge Apt!Stockbridge
- Secluded Cabin with Gorgeous Views near Stockbridge in the Berkshires of Massachusetts
- Tranquil 3 BR Stockbridge House with Private Deck!Stockbridge9.5
- Prospect BerkshiresNorth Egremont9.8
- Cabin with 3 Acres, Tennis Courts By 4 Ski MtnsSandisfield
- Spacious Guest Cottage Rental on Lake in The Berkshires, MassachusettsLanesborough
- East Otis Reservoir Cabin with Porch - Walk to Lake!East Otis
- Beautiful Cottage Rental on Lakeside Property in The Berkshires, MassachusettsLanesborough
- Buttonball InnSouth Egremont
- Berkshires Home on 11 Acres with Pond and 2 Fire Pits!Becket
- Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG9.0Pittsfield
- Impressive Family-Friendly Lake Cottage in The Berkshires, MassachusettsLanesborough
- 6 Mi to Tanglewood Peaceful Berkshire Apt!Richmond
- Tolland Lake Escape Kayaks Deck and Nature TrailsSandisfield
- Eastover Estate and Eco Village6.6Lenox
- half Mi to Jiminy Peak Condo with Pool and Hot TubHancock
- Steps to Downtown Stockbridge Home with Patio!Stockbridge
- Charming Cabin with Serene Lake Views for a Family Getaway near Pittsfield, MassachusettsRichmond
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