3. Martha’s Vineyard: Yes, there are amazing winter deals for Valentines Day in Martha’s Vineyard! Among your options are Valentine’s Day weekend packages offered by three of the Island’s top properties: the Harbor View Hotel and Vineyard Square Hotel, both in Edgartown, and the Mansion House Inn in Vineyard Haven. Bundle up and take a stroll, the sea and sky-scapes are unbelievably romantic in the winter.