Black Bear Cottages offers a quintessential Woodstock cottage experience. Our five unique cottages have been lovingly and individually updated to provide clean, modern comforts with charming country simplicity inside while retaining the original rustic character outside. Five cottages dispersed across six acres provides each cottage with a natural, private wooded setting.

Our Woodstock Cottages:
Sycamore | White Pine Knoll | Hickory Rock | Winding Brook | Hemlock Ledge

Just sitting on your cottage porch, in your yard, or strolling the wooded path through the property, is relaxing and refreshing. Each cottage has its own unique character. All have been newly decorated in a casual, country style using an eclectic mix of new and antique furnishings.

Our cottages are located less than two miles from the Woodstock Village Green, and only one mile from the legendary Byrdcliffe Art Colony. We are perfect for the experience of enjoying your own home in Woodstock. Those with cars have easy access to us, but so do those city dwellers who wish to take the bus up from NY Port Authority. Bicycles can be easily rented in town and beautiful country roads abound for walking and riding.

Black Bear Cottages in Woodstock is located on a wooded hillside on the historic Glasco Turnpike, at its intersection with Ricks Road. At the bottom of the hill, less than a mile away, is one of the Woodstock areas finest produce and gourmet delis, Sunfrost Farms. In good weather there are tables in the garden for enjoying light fare.

We want you to have a wonderful time in Woodstock, and each cottage always has the latest edition of the Woodstock Times, including the calendar of events, to inform you of the many fascinating events and activities going on each weekend.

Because each cottage has its own unique features, we would like to describe each so that you can choose the one best suited to you. Click here to see our cottages.