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From dream to reality: Living the island life

Epitomizing the charm and beauty of classic New England architecture, the Captain’s Cottages – inspired by the stately captain’s manors gracing Edgartown’s tree-lined streets – offer an unprecedented level of comfort, luxury and convenience.

These immaculate residences are serenely nestled upon the hotel’s manicured grounds – a mere 5-minute stroll to the exclusive shops, vibrant galleries and acclaimed restaurants of historic Edgartown.

But there’s more to this story than convenience; there’s the peace of mind you’ll experience by residing in a fully-managed vacation home with unlimited access to all the services and amenities of a world-class hotel.

It’s time to turn your dream into a reality. Your first step toward island living is just a conversation away with our real estate team. To make an appointment, tour a cottage or obtain more information, please contact us here.

Captain's Cottage Stewardship

Perhaps the most significant highlight to owning one of our Martha’s Vineyard cottages is the owners themselves. The private group of individuals who steward the Harbor View Hotel hold strong ties to the Vineyard. Their common bond is a deep appreciation for the island and an enduring commitment to protecting her spirit. Now you have the chance to join this select group, stewarding historic Harbor View for future generations and calling Edgartown home. This exclusive opportunity is limited to 18 individuals or families.

Contact us for more information on ownership and to schedule a private tour at the Harbor View Hotel's Captain's Cottages.

Luxury Services & Amenities

What separates the Captain’s Cottages from other Martha’s Vineyard homes for sale is the premier access to services and amenities that come with Harbor View Hotel. As one of Edgartown’s most luxurious hotels, Harbor View is dedicated to providing the attentiveness required for a memorable Vineyard vacation. Experience this luxurious treatment in the comfort of your own Edgartown condo.

Upcoming Events

Save 20 in 2020

New Year, New Savings in 2020!

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Brand New Offer

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Prepay and Save

Prepay and Save and Test

Are your Vineyard travel plans set in stone? If so, you’re eligible to save 10% off when you book our pre-paid and non-refundable rate. This rate requires payment in full at the time of booking. Reservation is not eligible for cancellation, refund or transfer.


Cancellations anytime after booking will result in forfeiture of deposit.

To guarantee your stay, this rate requires payment in full at the time of booking. Reservation is not eligible for cancellation, refund or transfer.

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