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Enter to Win A cottage experience on the vineyard

Win a Luxurious 2-Night Stay for Two ($3,900 Value)! Stay in a Captain’s Cottage at the Harbor View Hotel, where cozy comfort meets luxury. This exclusive offer is valid for stay dates between May 4 and June 20, 2024. Hurry, submit your entry by April 30, 2024, and stay tuned for the winner announcement by May 3, 2024.

Nestled within the beautifully landscaped grounds of Harbor View Hotel, the Captain’s Cottages represent the ideal balance of quaint cottage charm and the indulgent amenities of a luxury resort. Each cottage is a secluded haven, thoughtfully designed to ensure privacy while providing complete access to the hotel’s superior amenities and dining experiences. Experience a vacation redefined, where the homely feel of cottage living seamlessly blends with unparalleled hospitality.

Disclaimer: Enter to Win before April 30, 2024. A winner will be drawn by May 3, 2024. Offer applies to stay dates between May 4 and June 20, 2024, applicable exclusively to Captain’s Cottages. Captain’s Cottages vary in size and configuration and will be offered based on availability. Guest rooms in the Historical Building, Roxana, and the Presidential Skyhouse Wing are excluded from this offer. This offer is exclusive to new reservations and cannot be merged with other promotions or group reservations.

Enter To Win

Enter to win a two-night stay for two people in one of the beautiful Captain’s Cottages at Harbor View Hotel!




The Latest

Captain's Cottage Collins Loft living room at Harbor View Hotel on Martha's Vineyard.

The Cottage Life

Enjoy 30% off your stay in our Captain’s Cottage and up to $100 towards provisions. Upon your arrival, our team will stock your cottage with your favorite items.

Food & Drink

Mother’s Day at Harbor View Hotel 2024

Sunday, May 12th
Harbor View Hotel
11:00am - 3:00pm

Memorial Day Weekend 2024

May 24 - May 27
Harbor View Hotel

A trip to the beautiful Island of Martha's Vineyard is only a few clicks away.