Moshup Trail
About this property
Panoramic Views, Luxe Interiors & a Heated Pool Retreat
Set high above the Vineyard’s western edge, Windy Hill is a private Aquinnah estate that delivers jaw-dropping sunrises, spectacular sunsets, and sweeping views across the Elizabeth Islands, Menemsha Bight, and the Atlantic beyond. With a newly renovated interior and high-end design throughout, this compound blends natural beauty with effortless luxury.
The estate consists of a 4-bedroom, 4.5-bathroom Main House and a 2-bedroom, 1.5-bathroom Guest House, offering space, privacy, and comfort for larger groups or multi-generational stays. Each bedroom has stunning stylish finishes and thoughtful details throughout.
Rooms & spaces
Additional Details
Enjoy slow mornings and golden hour cocktails from multiple decks and patios, take a dip in the heated pool, challenge your crew to a game of bocce, or head down the path to the secluded South Shore beach just minutes away.
The Guest House features a screened-in porch perfect for summer lounging, and the entire property is equipped with central AC and heat for year-round comfort. With top-tier furnishings, appliances, and curated interiors, this is one of Aquinnah’s most striking and complete luxury retreats.
Available Summer 2026
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Cancellations
Please see our cancellation policy here.
Note
We always recommend making every effort to personally view a property before booking. We represent the condition, size, and location of each home as accurately as possible, although all information is deemed reliable but not guaranteed. As rental agents, we represent the landlord. Please also be aware that any home built prior to 1978 may contain lead paint. Various types of mold occur naturally on Martha’s Vineyard, and some individuals may be sensitive or have allergic reactions to them.