Best Cheshire Hotels

The Harbour House Inn B&B is an ideal spot for travelers wanting to discover the city. Visitors to Cheshire will find that the Harbour House Inn B&B is a fantastic accommodation choice. From the hotel, Pittsfield Municipal Airport is approximately 26km away. Pittsfield Municipal Airport is approximately 26km away by road. With multiple attractions nearby including Saint Mary of the Assumption Parish, Father Tom Campsite and Jones Nose Trailhead, guests will find plenty to keep themselves occupied. After a long day of sightseeing, guests can retire to the comfort of the hotel. Guests of this Cheshire hotel can make use of the parking facilities. According to our trusted guests, the facilities at this hotel are first-rate.

Located in Adams, The Trail in Adams - Berkshires’ Art Hotel is in the mountains, just a 4-minute walk from Adams Theater and a 2-minute drive from Susan B. Anthony Birthplace Museum. This bed & breakfast is 5.8 mi (9.4 km) from Massachusetts Museum of Contemporary Art and 11.1 mi (17.8 km) from Williams College. Take in the views from a terrace and a garden and make use of amenities such as complimentary wireless internet access. This bed & breakfast also features concierge services, an arcade/game room, and shopping on site. Featured amenities include express check-in, luggage storage, and a library. Free self parking is available onsite. Make yourself at home in one of the 9 air-conditioned rooms featuring DVD players. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Bathrooms feature showers, complimentary toiletries, and slippers. Conveniences include desks and a turndown service, and housekeeping is provided daily.

The Jiminy Peak Mountain Resort provides a great place for travelers to relax after a busy day. The Jiminy Peak Mountain Resort offers a pleasant stay in Hancock for those traveling for business or leisure. From the hotel, Pittsfield Municipal Airport is approximately 29km away. Pittsfield Municipal Airport is approximately 29km away by road. With multiple attractions nearby including Jiminy Peak Mountain Adventure Park, Bentley Brook and Ioka Valley Farm, guests will find plenty to keep themselves occupied. At the end of a busy day, travelers can unwind and relax in the hotel or go out and enjoy the city. For those driving themselves, parking is provided on site.

With a stay at Vacation Village in the Berkshires in Williamstown, you'll be a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain Coaster. This family-friendly condo is 1.8 mi (2.9 km) from Alpine Super Slide and 4.9 mi (7.9 km) from Mount Greylock State Reservation. Don't miss out on the many recreational opportunities, including an outdoor pool, an indoor pool, and a fitness center. This condo also features complimentary wireless internet access, concierge services, and an arcade/game room. Featured amenities include a business center, express check-out, and a 24-hour front desk. Free self parking is available onsite. Treat yourself to a stay in one of the 360 guestrooms, featuring fireplaces. Rooms have private patios. Kitchens are outfitted with refrigerators, stovetops, and microwaves. Conveniences include safes and coffee/tea makers, as well as phones with free local calls.

Located in Williamstown, Berkshire Valley Inn is in the mountains, within a 10-minute drive of Jiminy Peak Mountain Resort and Williamstown Theatre Festival. This hotel is 5.3 mi (8.5 km) from Waubeeka Golf Links and 8.5 mi (13.7 km) from Mount Greylock State Reservation Visitor Center. Take advantage of recreation opportunities such as a seasonal outdoor pool, or other amenities including complimentary wireless internet access and concierge services. This hotel also features a fireplace in the lobby and a banquet hall. A complimentary continental breakfast is included. Featured amenities include express check-in, express check-out, and luggage storage. Free self parking is available onsite. Make yourself at home in one of the 16 air-conditioned rooms featuring minibars. Complimentary wireless internet access is available to keep you connected. Bathrooms feature shower/tub combinations, hair dryers, and toothbrushes and toothpaste. Conveniences include coffee/tea makers and irons/ironing boards, and housekeeping is provided on request.

With a stay at Hotel On North in Pittsfield, you'll be within a 15-minute drive of Tanglewood Music Center and Berkshire Athenaeum. This hotel is 7.4 mi (11.9 km) from Jiminy Peak Mountain Resort and 0.4 mi (0.6 km) from Barrington Stage Company. Take advantage of recreation opportunities such as a fitness center, or other amenities including complimentary wireless internet access and concierge services. Take advantage of the hotel's room service. Wrap up your day with a drink at the bar/lounge. Featured amenities include a business center, dry cleaning/laundry services, and a 24-hour front desk. Free self parking is available onsite. Make yourself at home in one of the 45 air-conditioned rooms featuring minibars and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have bathtubs or showers and complimentary toiletries. Conveniences include safes and desks, and housekeeping is provided daily.

With a stay at Berkshire Inn, you'll be centrally located in Pittsfield, within a 15-minute drive of Tanglewood Music Center and Berkshire Museum. This motel is 8.2 mi (13.2 km) from Jiminy Peak Mountain Resort and 0.6 mi (1 km) from Colonial Theater. Take advantage of recreation opportunities such as a seasonal outdoor pool, or other amenities including complimentary wireless internet access and a television in a common area. Free self parking is available onsite. Make yourself at home in one of the 38 air-conditioned rooms featuring refrigerators and microwaves. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Conveniences include desks and irons/ironing boards, and housekeeping is provided daily.

Located in Williamstown, 1896 House Country Inn & Motels is a 5-minute drive from The Clark Art Institute and 5 minutes from Williams College. This inn is 3.6 mi (5.7 km) from Williamstown Theatre Festival and 7.3 mi (11.7 km) from Massachusetts Museum of Contemporary Art. Take in the views from a terrace and a garden and make use of amenities such as complimentary wireless internet access. Additional amenities at this inn include wedding services and tour/ticket assistance. At 1896 House Country Inn & Motels, enjoy a satisfying meal at the restaurant. Wrap up your day with a drink at the bar/lounge. Featured amenities include complimentary wired internet access, a business center, and luggage storage. Event facilities at this inn consist of conference space and a meeting room. Free self parking is available onsite. Make yourself at home in one of the 36 guestrooms.