Photograph courtesy of Douglas Elliman Realty
16 Allen Farm Road - Chilmark, MA
Rent it for: $10,000-$20,000 per week
While some parts of Martha's Vineyard feel decidedly posh, this estate sprawling 100+ acres embraces the New England island's agricultural past. The hilltop house was just built in 2018, but the property's original farmhouse dates back to 1773.Here, you can get fresh produce from the vegetable garden and eggs from the chickens before heading down to Lucy Vincent Beach or Chilmark Pond. The rural estate, which sleeps 10, has been in the same family's hands since 1762. Taking in the serene ocean views, it's easy to see why.Jesse Greenstein of Douglas Elliman holds the listing.