- NEW 6-Bedroom Retreat Book Your Summer GetawayLebanon Springs
- Massachusetts Lake House with Dock - Pets Welcome!New Marlborough
- The Greylock CabinFlorida
- The Allen HouseNorth Adams
- Berkshire Vacation Rentals 1900s Factory Turned Modern Berkshires RetreatGreat Barrington
- Beautiful Two-Bedroom Cabin Rental Set in the Forests of the Berkshires, MassachusettsWorthington Center
- Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4Hancock7.5
- 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 GorgeousHancock10.0
- Vintage Caboose Rental in Historic Small Town near Springfield, MassachusettsChester8.7
- Imaginative Octogonal Glass Treehouse on Seven Private Acres near Great Barrington, MAOtis
- 1 Mi to Vineyard Serene Berkshires Country EscapeRichmond10.0
- 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
- Modern Berkshires Farmhouse w Porch Fireplace Views Beaver Creek by AvantStayLee
- Beautiful House in the Woods, Huge Yard, Hot TubGreat Barrington
- Watercrafts and Dock Stunning Lakehouse in Becket!Becket
- Lee ManorLee
- Four-Bedroom Luxury House Rental on Pontoosuc Lake in the BerkshiresLanesborough
- 2 Mi to Norman Rockwell Museum Stockbridge Apt!Stockbridge8.0
- Secluded Cabin with Gorgeous Views near Stockbridge in the Berkshires of Massachusetts
- Tranquil 3 BR Stockbridge House with Private Deck!Stockbridge9.5
- Prospect BerkshiresNorth Egremont9.9
- Cabin with 3 Acres, Tennis Courts By 4 Ski MtnsSandisfield
- Elegant 7BR Estate with Pool & Hot Tub in BerkshiresNorth Egremont
- Private cottage close to shopping dining and skiing
- Spacious Guest Cottage Rental on Lake in The Berkshires, MassachusettsLanesborough
- Beautiful Cottage Rental on Lakeside Property in The Berkshires, MassachusettsLanesborough
- 8 Mi to Jiminy Peak Resort Mtn-View Home with DeckStephentown
- Buttonball InnSouth Egremont
- Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG9.0Pittsfield
- Quiet All-Season Creekside Escape in Upstate!North Hancock
- Impressive Family-Friendly Lake Cottage in The Berkshires, MassachusettsLanesborough
- 6 Mi to Tanglewood Peaceful Berkshire Apt!Richmond
- Brand New Barn HouseStockbridge10.0
- Steps to Downtown Stockbridge Home with Patio!Stockbridge8.0
- Charming Cabin with Serene Lake Views for a Family Getaway near Pittsfield, MassachusettsRichmond
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