- Cozy Mountain Cabin on Resort Property in Cultural BerkshireHancock10.0
- 6 Mi to Skiing Pet-Friendly Home in Pittsfield!Pittsfield
- Family-Friendly Richmond Cottage with Private YardPittsfield9.0
- 5 Bed / 3 bath Apt Near Jiminy Peak BerkshiresStephentown10.0
- Woodland Zen by AvantStay Modern Design PatioStockbridge
- Pet-Friendly Berkshires Home 1 Mi to New Lebanon7.0
- Holiday Inn Oak n Spruce Resort -1BD Sleep up to 4Lee
- Lakefront Hinsdale Home about 10 Mi to Pittsfield!Hinsdale
- Wilder House BerkshiresSheffield9.6
- 4 Mi to Skiing Cottage with Fire Pit in Richmond!Richmond
- COZY GUESTHOUSE Minutes Away From Hiking!New Marlborough9.5
- Urban Peak EscapeLenox10.0
- Monterey Home with Hot Tub, Pool and Game Room!Monterey
- Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone DecorHancock10.0
- The entire Stephentown Hotel. 28 person occupancyHancock10.0
- Berkshire Hideaway with Fire Pit and Playground!Canaan
- Berkshire Valley InnWilliamstown9.0
- Bright Boho Apt in 18th c Berkshire FarmhouseLanesborough9.0
- Berkshire Valley InnWilliamstown
- Becket Home with 3-Season Porch Walk to Lake AccessBecket
- Charming Apt in 18th c Berkshire FarmhouseLanesborough
- Water Street ApartmentsWilliamstown9.4
- Casa del BoscoTolland9.0
- Berkshire's Manor for Lasting MemoriesLee
- 2 Bed Berkshire Getaway minutes to Jiminy Peak SkiHancock9.8
- 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 Spacious Austerlitz Ski Cabin!
- 2 Bed Berkshire Getaway @ Stephentown HotelStephentown9.4
- Secluded Estate w Guest House Private Pond Gym Movie Theater Sunny Pond
- Berkshire Vacation Home in Lee - Pool is Open!Lee
- Cozy Rustic Apt in 18th c Berkshire FarmhouseLanesborough9.7
- 1 Mi to Dtwn Cottage with Large Yard in StockbridgeStockbridge
- Lake HavenMonterey
- Charming barn in the heart of the BerkshiresNew Marlborough
- Great Barrington Lakeside Getaway with Kayak and GrillGreat Barrington9.5
- Hudson Valley and The Berkshires GetawayHillsdale
- End of results -