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    Cockeysville, Maryland Boat Rentals & Yacht Charters

    Page 1 of 1 • 24 listings

    Cruise the Inner Harbor and beyond on a Monterey 350 Sport Yacht
    Powerboats in Baltimore · 6 guests

    Cruise the Inner Harbor and beyond on a Monterey 350 Sport Yacht

    5.0
    $325/hour
    Stunning 26FT Cabin Cruiser – Relax, Celebrate & Cruise Baltimore in Style
    Powerboats in Baltimore · 6 guests

    Stunning 26FT Cabin Cruiser – Relax, Celebrate & Cruise Baltimore in Style

    5.0
    $200/hour
    Perfect 10-Seater Pontoon for Cruising DMV Waters - Annapolis, Baltimore, & D.C.
    Powerboats in Baltimore · 10 guests

    Perfect 10-Seater Pontoon for Cruising DMV Waters - Annapolis, Baltimore, & D.C.

    New
    $275/hour
    House-Yacht for Relaxing on the Water in Quiet Luxury
    Powerboats in Baltimore · 6 guests

    House-Yacht for Relaxing on the Water in Quiet Luxury

    New
    $275/hour
    STARCRAFT LUXURY PARTY PONTOON IS FINALLY HERE!!BEST OF BALTIMORE WINNER 2022...
    Powerboats in Baltimore · 10 guests

    STARCRAFT LUXURY PARTY PONTOON IS FINALLY HERE!!BEST OF BALTIMORE WINNER 2022...

    5.0
    $290/hour
    42ft Party Yacht Best of Baltimore 2024-25 Winner!
    Events in Baltimore · 12 guests

    42ft Party Yacht Best of Baltimore 2024-25 Winner!

    5.0
    $400/hour
    Azimut 43 Yacht - Your Day, Your Itinerary!
    Events in Baltimore · 6 guests

    Azimut 43 Yacht - Your Day, Your Itinerary!

    New
    $685/hour
    38ft Seawind 1160 Luxury Sailing Catamaran in Essex, Maryland for 12 Guests
    Sailing in Essex · 12 guests

    38ft Seawind 1160 Luxury Sailing Catamaran in Essex, Maryland for 12 Guests

    5.0
    Snoozed - Active 27 Jun 2026
    Welcome Aboard Optimystic! Create a beautiful memory on the water.
    Sailing in Essex · 6 guests

    Welcome Aboard Optimystic! Create a beautiful memory on the water.

    5.0
    $150/hour
    Cruise the Chesapeake on Bay Lady
    Powerboats in Essex · 5 guests

    Cruise the Chesapeake on Bay Lady

    New
    Snoozed - Active 09 Jul 2026
    Quest Sportsman 12 Jon Boat: Perfect for rivers and lakes in Baltimore Highlands
    Fishing in Baltimore · 2 guests

    Quest Sportsman 12 Jon Boat: Perfect for rivers and lakes in Baltimore Highlands

    New
    $50/hour
    22’ Bayliner Cruiser with Onboard Water and Toilet - 8 People
    Powerboats in Dundalk · 8 guests

    22’ Bayliner Cruiser with Onboard Water and Toilet - 8 People

    New
    $125/hour
    Fishing Charter in Pasadena, Maryland
    Fishing in Riviera Beach · 6 guests

    Fishing Charter in Pasadena, Maryland

    5.0
    $840/day
    2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland
    Powerboats in Severna Park · 4 guests

    2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

    5.0
    $120/hour
    2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island
    Powerboats in Annapolis · 8 guests

    2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

    4.9
    $225/hour
    Pro line Center Console Magothy River - Perfect for fishing, exploring, cruising
    Powerboats in Severna Park · 12 guests

    Pro line Center Console Magothy River - Perfect for fishing, exploring, cruising

    5.0
    $65+/hour
    39ft Regal Powerboat for Charter | 13 Guests | Annapolis
    Events in Arnold · 13 guests

    39ft Regal Powerboat for Charter | 13 Guests | Annapolis

    New
    Superowner
    $550/hour
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
    Sailing in Rock Hall · 6 guests

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    5.0
    $150/hour
    43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland
    Sailing in Rock Hall · 6 guests

    43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

    5.0
    $136+/hour
    34' Hunter Cruising Monohull In Rock Hall, Maryland United States
    Sailing in Rock Hall · 4 guests

    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    4.6
    $275+/night
    34ft Sailing Yacht in Annapolis, Maryland
    Sailing in Annapolis · 4 guests

    34ft Sailing Yacht in Annapolis, Maryland

    New
    $250/hour
    Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis
    Powerboats in Annapolis · 6 guests

    Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis

    4.8
    $95+/hour
    Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
    Events in Annapolis · 8 guests

    Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

    5.0
    $300/hour
    45' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 32 Guests Capacity
    Powerboats in Annapolis · 32 guests

    45' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 32 Guests Capacity

    New
    Snoozed - Active 25 Aug 2026

    Top Destinations Nearby

    Cockeysville Reviews

    1. RK

      Richard

      34' Hunter Cruising Monohull In Rock Hall, Maryland United States

      Our group of four had a great three days onboard the Icarus. The boat was easy to sail and operate. No problems motoring around in the marinas, steers easy in reverse too. Jim was a great host, very responsive and knowledgeable. Highly recommend his boat to sail the Chesapeake!

    2. hN

      hornella

      2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

      It was a good choice i’m really glad i booked with them. we had a good day on my birthday, Very fun and enjoyable, The captain was good and kind. Thank you so very much!

    3. MB

      Mary

      2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

      Sunmi was extremely attentive - he was on time, had the boat ready to, went through review of the boat and we were off. We had a blast!! The boat drives very well. Great for an afternoon on the Chesapeake!

    4. JV

      Jakub

      Stunning 26FT Cabin Cruiser – Relax, Celebrate & Cruise Baltimore in Style

      Amazing, friendly captain and an incredibly memorable experience. Joseph worked closely with me to tailor my experience and plan my proposal to perfection. We are forever grateful!

    5. CC

      Carolina

      Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

      Highly recommend for your next outting! Great and quick communication, friendly and professional, super clean boat

    6. PM

      Pam

      Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

      Our trip was amazing start to end. The boat is beautiful and spacious. The captain is very thoughtful and has attention to all the details.

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