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Dundalk, Maryland Boat Rentals & Yacht Charters

Page 1 of 124 listings

 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
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...

4.6
Snoozed - Active 03 Aug 2026
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
$375/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
$250/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
22’ Bayliner Cruiser with Onboard Water and Toilet - 5 People
Powerboats in Dundalk · 8 guests

22’ Bayliner Cruiser with Onboard Water and Toilet - 5 People

New
$95/hour
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
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
Fishing Charter in Pasadena, Maryland
Fishing in Riviera Beach · 6 guests

Fishing Charter in Pasadena, Maryland

5.0
$840/day
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
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
$799+/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
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
$1100 2hrs| 39ft Regal | 12 Guests | Annapolis
Events in Arnold · 12 guests

$1100 2hrs| 39ft Regal | 12 Guests | Annapolis

5.0
Superowner
$550/hour
Pro line Center Console Magothy River - Perfect for fishing, exploring, cruising
Powerboats in Arnold · 10 guests

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

5.0
$80+/hour
Instant Book
42 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

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

5.0
$150+/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
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
2020 Misty Harbor Tritoon for 12 people in Annapolis
Powerboats in Annapolis · 12 guests

2020 Misty Harbor Tritoon for 12 people in Annapolis

5.0
$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
Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch
Sailing in Annapolis · 6 guests

Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch

5.0
Snoozed - Active 26 Aug 2026
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
Quick Private Annapolis Harbor Boat Ride - Oceanus 12 VST Inflatable
Powerboats in Annapolis · 6 guests

Quick Private Annapolis Harbor Boat Ride - Oceanus 12 VST Inflatable

5.0
Snoozed - Active 26 Aug 2026

Dundalk Reviews

  1. LF

    Linda

    Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch

    Stephen was wonderful! A few days before our sailing trip, the weather forecast looked questionable, but he stayed in touch the entire time, offering to start earlier or even reschedule for a different day if needed. He was incredibly flexible and genuinely wanted to make sure we had the best possible experience. Thanks to his communication and commitment, we had a fantastic trip. I highly recommend sailing with Stephen!

  2. SN

    Sarah

    Quick Private Annapolis Harbor Boat Ride - Oceanus 12 VST Inflatable

    Stephen is the type of guy who makes the whole experience of boating on the water a once-in-a-lifetime feat. From his warm demeanor to his approach to helping each guest he takes on, to his allowance of people driving his own boat, his guidance along the way makes each and every guest wanting to come back for more. As soon as he met me outside the marina, he steered us on his boat into the waters of Annapolis Harbor, and did not hesitate to explain the landmarks we would be seeing alongside how boating actually works. For a newbie, he guided me on the logistics of how to drive his boat, which is something I thought was very warm and interesting. Stephen is an extremely friendly guy and is willing to do anything it takes to make his guests feel respected, relaxed and willing to know all about “the way of the water”. I learned a lot from him, and was left feeling fulfilled by my visit. I highly recommend Stephen to anyone who wants to do boating on the waters of Annapolis because he is a very knowledgeable and friendly person who always goes the extra mile.

  3. Geoffrey

    Geoffrey

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

    Icarus is a great boat and very well equipped. The sails and everything else on the vessel are in great shape and the fact it only draws 4' 6" is perfect for the Chesapeake. I spent a week on Icarus and everything worked well. The value of chartering Icarus is undeniable. I plan to charter Icarus again. Icarus has a lot of sail area, so if the winds are strong douse the headsail early.

  4. Sarah

    Sarah

    $1100 2hrs| 39ft Regal | 12 Guests | Annapolis

    An absolutely fantastic experience from start to finish! The captain was wonderful and the scenery was breathtaking, making for an unforgettable trip out on the water. The boat was spotless, the booking process was a breeze, and everything ran like clockwork — couldn’t recommend it more highly!

  5. LM

    Liz

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

    Charles was an outstanding guide. Before the outing (which was a birthday gift for my fiancé) he even offered to pick up a cake so that it could be a surprise. He and his wife made us feel at home right away as if we were out just sailing with friends. It was a gorgeous late afternoon / sunset sail with the option of swimming and cooking on the boat. We didn't rush back. Riding on the bow was so relaxing. He took time explaining sailing tips to my fiancé and let him drive the boat for awhile. Communication was clear. We'd love to book again with Charles and Renee!

  6. 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!