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    All listings in Massachusetts

    Incredible sailboat rentals in Massachusetts, United States.

    5.0
    (260 Reviews)

    Page 2 of 2 • 27 listings

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    • Highest Rated
    Private Sailing Charter on Martha's Vineyard
    Sailing in Tisbury · 6 guests

    Private Sailing Charter on Martha's Vineyard

    5.0
    Snoozed - Active 02 Jul 2026
    Come Sail Newport, Narragansett Bay & Beyond with 50ft Jeanneau Sun Odyssey
    Sailing in Jamestown · 6 guests

    Come Sail Newport, Narragansett Bay & Beyond with 50ft Jeanneau Sun Odyssey

    New
    Snoozed - Active 03 May 2026
    Martha's Vineyard Best Sailing Charters on 60' Luxury Ketch
    Sailing in Tisbury · 6 guests

    Martha's Vineyard Best Sailing Charters on 60' Luxury Ketch

    New
    Snoozed - Active 03 May 2026

    Top Destinations Nearby

    Sailing Reviews in Massachusetts

    1. MR

      MV Landmarks

      Private Sailing Charter on Martha's Vineyard

      We really enjoyed sailing on the Miss Marilyn in Vineyard Sound. The sail was amazing and the captain was so knowledgeable and engaging. We most highly recommend the experience!

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