Hotels with free parking in Stephentown

Enjoy a family-friendly resort with indoor and outdoor pools, fitness center, and stunning views in the Berkshires.

Ski-in/ski-out resort with 2 hot tubs, multiple dining options, and family-friendly amenities in Hancock, Massachusetts.

Stylish 2BR suite with ski-in/ski-out access, swimming pool, sauna, and hot tub in Hancock, Massachusetts.

Comfortable hotel with a fitness center, complimentary breakfast, and meeting space in Pittsfield, Massachusetts.

Lodge with indoor pool, hot tub, and picnic area near golf course and Tanglewood Music Center in Pittsfield.

Enjoy a seasonal outdoor pool and free Wi-Fi in this centrally located motel in Pittsfield, Massachusetts.

Enjoy an outdoor pool and garden at this motel, conveniently located near Guido's Marketplace in Lenox.

Enjoy a stay with an indoor pool, hot tub, and complimentary breakfast in Pittsfield, Massachusetts.

Comfortable guesthouse in Pittsfield with free parking, express check-in, and a terrace for scenic views.