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    All listings in Chesapeake Bay

    Incredible sailboat rentals in Chesapeake Bay, United States.

    5.0
    (391 Reviews)

    Page 2 of 2 • 33 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!
    Sailing in Annapolis · 10 guests

    DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!

    New
    $232+/hour
    Sail on the Potomac in Washington, DC aboard the 28ft Hunter Sailboat
    Sailing in Washington · 6 guests

    Sail on the Potomac in Washington, DC aboard the 28ft Hunter Sailboat

    New
    $280/hour
    Instant Book
    Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours
    Sailing in Saint Michaels · 6 guests

    Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours

    New
    $400/hour
    Sail the Chesapeake Bay, Atlantic Coast or the Caribbean Islands in style! Charter this Jeanneau Sun Odyssey 509
    Sailing in Deltaville · 8 guests

    Sail the Chesapeake Bay, Atlantic Coast or the Caribbean Islands in style! Charter this Jeanneau Sun Odyssey 509

    New
    $524+/day
    VIKO S 35 Sailboat in Deale
    Sailing in Deale · 6 guests

    VIKO S 35 Sailboat in Deale

    New
    $298/hour
    41’ Bristol Sailboat Charter in Solomons Island, MD
    Sailing in Solomons · 6 guests

    41’ Bristol Sailboat Charter in Solomons Island, MD

    New
    $90/hour
    VIKO 30 Premium Sailing Yacht In Deale, MD
    Sailing in Deale · 5 guests

    VIKO 30 Premium Sailing Yacht In Deale, MD

    New
    $925/day
    34ft Sailing Yacht in Annapolis, Maryland
    Sailing in Annapolis · 4 guests

    34ft Sailing Yacht in Annapolis, Maryland

    New
    $250/hour
    STARZ -Lagoon 42 Catamaran in Chesapeake Bay
    Sailing in Annapolis · 13 guests

    STARZ -Lagoon 42 Catamaran in Chesapeake Bay

    5.0
    Snoozed - Active 02 Oct 2025

    Sailing Reviews in Chesapeake Bay

    1. MR

      Matt

      STARZ -Lagoon 42 Catamaran in Chesapeake Bay

      Great experience and our family and friends had a wonderful time. Clean boat and fun crew to help us celebrate a special occasion. Highly recommend!

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