Best hotels in Pittsfield

Best hotels in Pittsfield: the best-rated on Staylist is Hotel on North (AI score 9.0, typically $222 a night). Staylist lists 6 hotels in Pittsfield, United States, each with a booking link.

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  1. Hotel on North
    19.0Hotel on North3-star$222 / night
  2. Hilton Garden Inn Lenox Pittsfield
    29.1Hilton Garden Inn Lenox Pittsfield3-star$187 / night
  3. Cobblestone Hotel & Suites Pulaski/Green Bay
    37.5Cobblestone Hotel & Suites Pulaski/Green Bay2-star$101 / night
  4. 46.8Best Western Plus Berkshire Hills Inn SuitesPittsfieldCheck live price →
  5. 55.7Berkshire InnPittsfieldCheck live price →
  6. 65.4Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield$145 / night

Previously observed price; confirm current price and availability. Data updated 2 October 2026. How Staylist ranks hotels.

Best Hotels in Pittsfield (2026): 6 Rated · Staylist World