Hotels in Cheshire

Charming bed & breakfast in the Berkshires with a garden, terrace, and free Wi-Fi, just a short walk from Adams Theater.

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

Enjoy a health club and indoor pool at this centrally located hotel in Pittsfield, close to local attractions.

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

Comfortable motel in Pittsfield with air-conditioned rooms, refrigerators, microwaves, and complimentary breakfast.

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

Hotel with a garden, terrace, and free parking, offering 24-hour front desk service and free Wi-Fi in Adams, Massachusetts.

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

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