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    All listings in Massachusetts

    Incredible sailboat rentals in Massachusetts, United States.

    5.0
    (232 Reviews)

    Page 2 of 2 • 26 listings

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    • Price: High to low
    • Highest Rated
    Luxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in Boston
    Sailing in Boston · 8 guests

    Luxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in Boston

    New
    $550/hour
    Instant Book
    Authentic 122ft Tall Ship Schooner Adventure - A National Historic Landmark!
    Sailing in Gloucester · 60 guests

    Authentic 122ft Tall Ship Schooner Adventure - A National Historic Landmark!

    New
    $1,200+/hour

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