Hotels with parking 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 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.

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

Enjoy an indoor pool, hot tub, and fitness center at this hotel in the heart of North Adams, steps from local attractions.