Bed and Breakfast Mill River

Walk to Downtown: Pet-Friendly Millerton Home!

Eastgate Inn B&B

Gateways Inn

Private cottage close to shopping dining and skiing

Lakefront Escape w/ Dock! Hudson Valley Home

Walk to Dining: Downtown Lenox Guest House!

33 Main

Copake Lakes Hidden Treasure

Lakeridge Litchfield townhouse pool tennis skiing

Spencertown Inn

Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Peaceful Goshen Cottage w/ Screened Porch & Views!

1 Mi to Vineyard: Serene Berkshires Country Escape

Waterfalls and Trails at 'The Mills At Green Hole'

Berkshire Mountain Lodge

The Inn at Richmond

The Woodridge Retreat

13 Mi to Catamount Mountain Resort: Studio w/ Deck

Stylish Pine Plains Home Near Parks & Hiking!

Litchfield Retreat, Wineries, Foliage & Skiing

Elegant Pittsfield Home Near Downtown & Skiing!

Spacious Historic Home in the Berkshires!

Cornwall Inn