The Wind in the Pines motel is surrounded by a lovely arrangement of flower gardens by the pool. Studios with mini-kitchens, cable TVs, and outdoor grills are among the available rooms. The apartments at Wind in the Pines come equipped with a television, a videocassette player, and window air conditioning. Microwaves and mini-refrigerators are standard in kitchens. The resort is a two-story motel converted to a resort; all units are non-smoking, and a car is recommended to fully enjoy the area. Pets are not permitted.

Wind in the Pines provides family-friendly recreational activities throughout the winter and summer. The most well-liked sports are fishing, hiking, and snow skiing. Due to its ideal location in the Berkshire Mountains of western Massachusetts, there are plenty of sights to see, such as the Norman Rockwell Museum, Stockbridge's stores and galleries, and Tanglewood, the summer residence of the Boston Symphony Orchestra. A stay at Wind In The Pines year-round provides access to a range of cultural events, outdoor pursuits, shopping, fine dining, and antiques. Tanglewood, the Boston Symphony's and Boston Pops' summer home, Williamstown Theatre Festival, and Jacobs Pillow Dance Theater are all nearby. Due to its Berkshires location, there are numerous sights to see, including Mount Greylock, the Appalachain Trail, and Stockbridge's main street.