NEED HELP on Massachusetts Landlord/Tenant question

[Jayme Duff]

I'm exploring the opportunity to invest in a small seasonal rental property in Massachusetts.  The property has deeded beach rights and is a short walk from the ocean and a small community beach.  The seasonal rentals in the area are strong and my plan is to place an off season tenant in this fully furnished property between October 1 through April 30th at market (or slightly below) market rent.  I would like to book the property at much higher short-term seasonal rent rates between May 1 and September 30th.

Has anyone had any experience with a mix of seasonal and off season rental for the same property in Massachusetts?  Does anyone know the laws if having no experience?

Thanks in advance

Jayme