- NEW 6-Bedroom Retreat Book Your Summer GetawayLebanon Springs
- Cozy Mountain Cabin in Berkshire ResortHancock10.0
- Element Lenox Berkshires7.7Lenox
- Piebald Mountain Pet Friendly Tents, Petersburg, New YorkPownal
- Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4Hancock9.2
- Woodland Zen by AvantStay Modern Design PatioStockbridge
- 2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7Hancock5.0
- Disney Wonderland Suite at Jiminy-Ski On Off Mtn - Must See Stitch and Mickey MagicHancock10.0
- Lakefront Hinsdale Home about 10 Mi to Pittsfield!Hinsdale
- Wilder House BerkshiresSheffield9.5
- Cabin Perfect for Nature LoversStephentown
- Cozy Berkshires Stay, Mins from Ski SlopesLebanon Springs
- COZY GUESTHOUSE Minutes Away From Hiking!New Marlborough9.5
- Urban Peak EscapeLenox10.0
- The entire Stephentown Hotel. 28 person occupancyHancock10.0
- The Revival HouseAdams7.7
- 1 Mi to Dtwn Beautiful Home in Williamstown!Williamstown
- Light-filled Carpenter's Cottage in StockbridgeStockbridge10.0
- Becket Home with 3-Season Porch Walk to Lake AccessBecket8.0
- Doctor Sax House9.1Lenox
- Secluded Berkshires Estate Private PondPoolTheater Gym Sunny Pond
- Catamount LodgingHillsdale
- Stay Near Ski Berkshires, Mid-Week & Promo Deals!
- Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator Pool and LobbyHancock7.0
- Berkshire House StayLee
- 2 Bed Berkshire Getaway minutes to Jiminy Peak SkiHancock9.9
- Berkshires Studio Apartment at the Stephentown HotelHancock
- Lake Views and Dock Access - Pittsfield Cottage!Pittsfield
- Stunning All-Season Renovated Barn Escape!East Chatham
- Hudson Valley and The Berkshires CottageHillsdale10.0
- Stylish Rural Sanctuary Perfect for Every Season!East Chatham
- Private Hot Tub Hudson Valley Cabin Retreat!
- Secluded Estate w Guest House Private Pond Gym Movie Theater Sunny Pond
- 8 Mi to Tanglewood and Butternut Ski Spacious Home!8.0
- Berkshire Vacation Home in Lee - Pool is Open!Lee
- 1 Mi to Dtwn Cottage with Large Yard in StockbridgeStockbridge
- Huttopia BerkshiresHancock9.0
- 4 Mi to Great Barrington Berkshires Retreat!Sheffield
- Charming 6 Bdrm Countryside Stay, Sauna and HotTubNorth Egremont
- Hudson Valley and The Berkshires GetawayHillsdale
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