- Cozy Escape in a Suite near Bryant Mountain State Forest in MassachusettsHawley
- NEW 6-Bedroom Retreat Book Your Summer GetawayLebanon Springs
- Renovated Lakefront House with Dock Pets Welcome!New Marlborough
- Unique and Eclectic Small Town Suite Rental in MassachusettsHawley
- Element Lenox BerkshiresLenox
- Pet-Friendly Bell Tent with Views of Taconic Mountains for a Great Escape in Nature in Petersburg, New YorkWilliamstown
- Stunning and Secluded Luxury Barn for a Family Getaway in the Berkshires, MassachusettsGreat Barrington
- Beautiful Two-Bedroom Cabin Rental Set in the Forests of the Berkshires, MassachusettsHinsdale
- Historic, Waterfront Suite Rental close to Boston, MassachusettsHawley
- Walk to Ski Slopes Jiminy Peak Resort Getaway!Hancock
- Cozy Stockbridge Cabin - Walk to Beach and Lake!Stockbridge9.0
- Trail Access Berkshires Gem with Rooftop Deck!Lee
- Cozy Berkshires Stay, Mins from Ski SlopesLebanon Springs
- Modern and Family-Friendly Vacation Rental in the Berkshires near Great BarringtonMonterey
- Vintage Caboose Rental in Historic Small Town near Springfield, MassachusettsChester
- Imaginative Octogonal Glass Treehouse on Seven Private Acres near Great Barrington, MAGreat Barrington
- Lakeside Berkshires EscapeMonterey
- 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
- Watercrafts and Dock Stunning Lakehouse in Becket!Becket
- The Revival HouseAdams
- Four-Bedroom Luxury House Rental on Pontoosuc Lake in the BerkshiresLanesborough
- Secluded Cabin with Gorgeous Views near Stockbridge in the Berkshires of MassachusettsStockbridge
- Light-filled Carpenter's Cottage in StockbridgeStockbridge10.0
- Creative Moutain Getaway with Live Music close to Boston, MassachusettsHawley
- Spacious Guest Cottage Rental on Lake in The Berkshires, MassachusettsLanesborough
- Modern and Luxurious Cabin Rental on Estate Ranch in The Berkshires of MassachusettsLenox
- Secluded Berkshires Estate Private PondPoolTheater Gym Sunny Pond
- Beautiful Cottage Rental on Lakeside Property in The Berkshires, MassachusettsLanesborough
- Catamount LodgingHillsdale
- Stay Near Ski Berkshires, Mid-Week & Promo Deals!
- Impressive Family-Friendly Lake Cottage in The Berkshires, MassachusettsLanesborough
- 6 Mi to Tanglewood Peaceful Berkshire Apt!Richmond
- 8 Mi to Tanglewood and Butternut Ski Spacious Home!
- half Mi to Jiminy Peak Condo with Pool and Hot TubHancock
- Huttopia BerkshiresHancock
- Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of MassachusettsHawley
- Airy Upstate Getaway with a View
- 4 Mi to Great Barrington Berkshires Retreat!Sheffield
- Charming Cabin with Serene Lake Views for a Family Getaway near Pittsfield, MassachusettsPittsfield
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