B&B Monument Mountain

Heart of the Berkshires Motel

Summer and Fall in Sheffield with Monthly Special Pricing Available

The Old Inn On The Green

The Mill River Cabin with Fireplace and River View!

Berkshire Vacation Rentals: Private Cabin On Over 12 Acres Of Woods

Spacious Historic Home in the Berkshires!

Elegant Pittsfield Home Near Downtown and Skiing!

Historic New Lebanon Hideaway on 33 Private Acres!

Chatham Travel Lodge

COZY GUESTHOUSE Minutes Away From Hiking!

Waterfalls and Trails at The Mills At Green Hole

Restored Historic Home Half Mile to Ski Resort!

Becket Home with 3-Season Porch Walk to Lake Access

Ashley Falls Home with Fire Pit Hike and Ski!

Hudson Valley Hot Tub Sauna Fire Pit Games

Thrill & Chill Ski & Sauna in Winter Wonderland

Charming Claverack Retreat with Serene Deck!

Copake Lakes Hidden Treasure

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

2 Bed Berkshire Getaway @ Stephentown Hotel

2 Bed Berkshire Getaway minutes to Jiminy Peak Ski

5 Bed / 3 bath Apt Near Jiminy Peak Berkshires

The entire Stephentown Hotel. 28 person occupancy

Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts