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Top 10 Hotels in The Berkshires

See all 144 Properties in The Berkshires
33 Main

33 Main

33 Main Street, Lenox
    4.0 out of 5.0
     
     

    Located in the heart of Lenox, this bed & breakfast is within a 10-minute walk of Lenox Library and Ventfort Hall Mansion and Gilded Age Museum. Shakespeare ...

    33 Main$329

    33 Main$329
    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd, Hancock
      3.0 out of 5.0
       
       

      Situated in Hancock, this condo building is within 9 mi (15 km) of Mount Greylock State Reservation Visitor Center, Pittsfield State Forest, and Waubeeka Golf ...

      Vacation Village in the Berkshires$135

      Vacation Village in the Berkshires$135
      Cranwell Spa and Golf Resort

      Cranwell Spa and Golf Resort

      55 Lee Road, Lenox
        3.5 out of 5.0
         
         

        Situated in Lenox, this spa resort is within 2 mi (3 km) of The Mount, Ventfort Hall Mansion and Gilded Age Museum, and Lenox Library. Shakespeare and Company ...

        Cranwell Spa and Golf Resort$159

        Cranwell Spa and Golf Resort$159
        Hotel On North

        Hotel On North

        297 North Street, Pittsfield
          3.5 out of 5.0
           
           

          Situated in Pittsfield, this hotel is within a 10-minute walk of Berkshire Museum, Berkshire Athenaeum, and Colonial Theater. Canoe Meadows Wildlife Sanctuary ...

          Hotel On North$149

          Hotel On North$149
          Yankee Inn

          Yankee Inn

          461 Pittsfield Rd, Lenox
          • Free Cancellation
          • Reserve now, pay when you stay
          2.5 out of 5.0
           
           

          Located in the heart of Lenox, this hotel is 0.5 mi (0.9 km) from Kennedy Park and within 3 mi (5 km) of Pleasant Valley Wilderness Sanctuary and Arrowhead Museum. ...

          Yankee Inn$92

          Yankee Inn$92
          Best Western Plus Berkshire Hills Inn & Suites

          Best Western Plus Berkshire Hills Inn & Suites

          1350 W Housatonic St, Pittsfield
          • Free Cancellation
          • Reserve now, pay when you stay
          2.5 out of 5.0
           
           

          Located in the heart of Pittsfield, this hotel is 1.7 mi (2.8 km) from Hancock Shaker Village and 2.9 mi (4.7 km) from Bousquet Ski Area. Colonial Theater and ...

          Best Western Plus Berkshire Hills Inn & Suites$92

          Best Western Plus Berkshire Hills Inn & Suites$92
          The Briarcliff Motel

          The Briarcliff Motel

          506 Stockbridge Road, Great Barrington
            2.0 out of 5.0
             
             

            Situated in Great Barrington, this motel is 1.6 mi (2.7 km) from Beartown State Forest and within 6 mi (10 km) of Mission House and Berkshire Theatre Festival. ...

            The Briarcliff Motel$140

            The Briarcliff Motel$140
            The Red Lion Inn

            The Red Lion Inn

            30 Main Street, Stockbridge
              3.5 out of 5.0
               
               

              This family-friendly Stockbridge hotel is located in the historical district, within a 15-minute walk of Mission House, Berkshire Theatre Festival, and Naumkeag. ...

              The Red Lion Inn$175

              The Red Lion Inn$175
              The Williams Inn

              The Williams Inn

              1090 Main Street, Williamstown
              • Free Cancellation
              • Reserve now, pay when you stay
              3.0 out of 5.0
               
               

              Situated in Williamstown, this hotel is within a 5-minute walk of Williamstown Historical Museum and 62 Center for Theater and Dance. Chapin Library of Rare ...

              The Williams Inn$145

              The Williams Inn$145
              Shaker Mill Inn

              Shaker Mill Inn

              7 Albany Road, West Stockbridge
                2.5 out of 5.0
                 
                 

                Located in the heart of West Stockbridge, this spa bed & breakfast is within 6 mi (10 km) of Berkshire Botanical Garden, Tanglewood Music Center, and Norman ...

                Shaker Mill Inn$140

                Shaker Mill Inn$140
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