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    Deale, Maryland Boat Rentals

    Page 1 of 1 • 24 listings

    VIKO S 35 Sailboat in Deale
    Sailing in Deale · 6 guests

    VIKO S 35 Sailboat in Deale

    New
    $298hour
    Cruise the Chesapeake Bay on a beautiful 34ft Maxum Yacht
    Powerboats in Deale · 6 guests

    Cruise the Chesapeake Bay on a beautiful 34ft Maxum Yacht

    5.0
    $250hour
    Charter 44' Orana Cruising Catamaran In Deale, Maryland
    Sailing in Deale · 10 guests

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    5.0
    $2,600day
    Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland
    Events in North Beach · 8 guests

    Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland

    5.0
    $400hour
    Experience the Serenity of Sailing SV Magic
    Sailing in Mayo · 6 guests

    Experience the Serenity of Sailing SV Magic

    4.8
    $125hour
    The Licensed Captain of this 42ft Sailboat, provides charters on Chesapeake Bay.
    Sailing in Mayo · 6 guests

    The Licensed Captain of this 42ft Sailboat, provides charters on Chesapeake Bay.

    5.0
    $175hour
    Instant Book
    Maxum 30ft Yacht! Escape for a day on the Chesapeake
    Events in Selby-on-the-Bay · 6 guests

    Maxum 30ft Yacht! Escape for a day on the Chesapeake

    New
    $365hour
    31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD
    Powerboats in Selby-on-the-Bay · 12 guests

    31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

    5.0
    $250hour
    43ft Cruiser Express Yacht for Daily Charter
    Events in Selby-on-the-Bay · 8 guests

    43ft Cruiser Express Yacht for Daily Charter

    5.0
    $400hour
    Pristine Hooligan Departs from a Private Pier with a Captain and Fuel INCLUDED
    Powerboats in Annapolis · 5 guests

    Pristine Hooligan Departs from a Private Pier with a Captain and Fuel INCLUDED

    New
    $200hour
    Chaparral SSX 27ft - Captained Private Charter - Watersports Included!!
    Powerboats in Edgewater · 6 guests

    Chaparral SSX 27ft - Captained Private Charter - Watersports Included!!

    New
    $200hour
    Bentley 220 Cruise Pontoon for rent in Edgewater
    Powerboats in Edgewater · 10 guests

    Bentley 220 Cruise Pontoon for rent in Edgewater

    New
    $400hour
    Charter 42' Lagoon Catamaran in Annapolis, MD
    Sailing in Edgewater · 12 guests

    Charter 42' Lagoon Catamaran in Annapolis, MD

    5.0
    $400hour
    Relax in Edgewater and Annapolis
    Powerboats in Edgewater · 10 guests

    Relax in Edgewater and Annapolis

    New
    $200hour
    Enjoy a Day on the Bay and Cruise the South River
    Powerboats in Annapolis · 6 guests

    Enjoy a Day on the Bay and Cruise the South River

    New
    $135-$160hour
    30ft Bowrider! Enjoy a day on the water around the Chesapeake Bay in Maryland!
    Powerboats in Annapolis · 8 guests

    30ft Bowrider! Enjoy a day on the water around the Chesapeake Bay in Maryland!

    3.7
    Snoozed - Active 02 Jan 2025
    Fully Crewed Annapolis Sailing Cruises
    Sailing in Annapolis · 6 guests

    Fully Crewed Annapolis Sailing Cruises

    New
    $175person
    Historical Annapolis Private Boat Cruise onboard a beautiful Swift Trawler!
    Events in Annapolis · 6 guests

    Historical Annapolis Private Boat Cruise onboard a beautiful Swift Trawler!

    5.0
    Snoozed - Active 02 Jun 2024
    50ft Catamaran Charter with Water Toys - Annapolis, MD
    Sailing in Annapolis · 12 guests

    50ft Catamaran Charter with Water Toys - Annapolis, MD

    New
    $400hour
    41' Lagoon Catamaran in Maryland
    Sailing in Annapolis · 12 guests

    41' Lagoon Catamaran in Maryland

    5.0
    Superowner
    Best of 2023
    $390hour
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland
    Sailing in Annapolis · 6 guests

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    5.0
    Superowner
    Best of 2023
    $138-$150hour
    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
    $250hour
    Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis
    Powerboats in Annapolis · 6 guests

    Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis

    4.8
    $95-$150hour
    34ft Sailing Yacht in Annapolis, Maryland
    Sailing in Annapolis · 4 guests

    34ft Sailing Yacht in Annapolis, Maryland

    New
    $250hour

    Top Destinations Nearby

    Deale Reviews

    1. Noelle

      Noelle

      Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

      My group and I had an amazing time! If you’re looking to have a great experience make sure to book with Captain McCoy. The boat was very clean. Getting on board was simple and finding the dock was easy. Also enjoyed stopping in the middle of our trip to just enjoy the weather and laying out on the front of the boat. I’d definitely book again!

    2. KC

      Kevin

      Charter 42' Lagoon Catamaran in Annapolis, MD

      Adam Yearwood is a fantastic captain! His boat is beautiful and he is well organized. We did a team outing sailing around the Chesapeake and had an awesome time - I highly recommend working with Adam!

    3. LW

      Lianna

      Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

      Captain McCoy was wonderful! Very accommodating and communicative. Our group had a great time!

    4. Liz

      Liz

      Cruise the Chesapeake Bay on a beautiful 34ft Maxum Yacht

      Captain Steve was incredible. He made our two hour boat outing experience unforgettable. We stopped around monuments to snap some scenic photos and even when we got caught in some rain, we all were fully covered in the inside of the boat. We will certainly book again soon!!

    5. Danika

      Danika

      Charter 44' Orana Cruising Catamaran In Deale, Maryland

      We had the best time! Everything was perfect! Rob communicated well! The boat looked exactly like the pictures. It was enough space for my 10 guest party! We sailed out for 7hrs and it still didn’t feel like enough time! I’m so glad I went with this boat and will be using it again in the future. Best birthday ever!!!

    6. JH

      Jennifer

      Charter 44' Orana Cruising Catamaran In Deale, Maryland

      Rob was so communicative and helpful throughout the entire booking process, and our experience on the boat was even better! Not only was it a beautifully appointed vessel, but our captain Adam took such wonderful care of our group. We can never outdo this day-- just plan when we can do it again!

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