B&B Monument Mountain

Elegant Pittsfield Home Near Downtown and Skiing!

Historic New Lebanon Hideaway on 33 Private Acres!

Chatham Travel Lodge

COZY GUESTHOUSE Minutes Away From Hiking!

A-Frame Cabin with Furnished Deck in Becket!

Cabin with 3 Acres, Tennis Courts By 4 Ski Mtns

Waterfalls and Trails at The Mills At Green Hole

Becket Home with 3-Season Porch Walk to Lake Access

Haddock Hill House

Ashley Falls Home with Fire Pit Hike and Ski!

Pittsfield Home with Deck - 12 Mi to Jiminy Peak!

Kayaks, Sauna & Family Relax & Play

Charming Claverack Retreat with Serene Deck!

Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak

Autumn Hill Lakehouse

2 Bed Berkshire Getaway minutes to Jiminy Peak Ski

2 Bed Berkshire Getaway @ Stephentown Hotel

5 Bed / 3 bath Apt Near Jiminy Peak Berkshires

The entire Stephentown Hotel. 28 person occupancy

Bright Boho Apt in 18th c Berkshire Farmhouse

Micosta Leisure Inn

Old Dutch Inn

Deluxe Ski On Off 1BR Suite Sleeps 4 on Jiminy Mtn

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4