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Chester, Maryland Boat Rentals - 2023

24 listings
46ft Chesapeake Motor Yacht Charter in Stevensville, Maryland
Fishing in Stevensville · 6 guests

46ft Chesapeake Motor Yacht Charter in Stevensville, Maryland

New
$750day
38' Center Console - up to 6 Guests from Stevensville, MD
Powerboats in Stevensville · 6 guests

38' Center Console - up to 6 Guests from Stevensville, MD

5.0
$300hour
Pershing 65 Power Mega Yacht Rental in Stevensville, Maryland
Events in Stevensville · 6 guests

Pershing 65 Power Mega Yacht Rental in Stevensville, Maryland

New
$550hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$300hour
Fully Crewed Annapolis Sailing Cruises
Sailing in Annapolis · 6 guests

Fully Crewed Annapolis Sailing Cruises

New
$175person
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
$170hour
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
$250hour
Sail the Sea on the Pintita
Sailing in Annapolis · 20 guests

Sail the Sea on the Pintita

New
$500-$750hour
Luxury yacht with Captain for 8 passengers to your Annapolis waterways
Events in Annapolis · 8 guests

Luxury yacht with Captain for 8 passengers to your Annapolis waterways

5.0
$250hour
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
Sailing in Annapolis · 6 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

5.0
Superowner
Best of 2023
$138-$150hour
Come take a cruise on the Annapolis Jet Boat
Powerboats in Annapolis · 11 guests

Come take a cruise on the Annapolis Jet Boat

New
$500hour
41' Lagoon Catamaran in Maryland, United States
Sailing in Annapolis · 12 guests

41' Lagoon Catamaran in Maryland, United States

5.0
Superowner
Best of 2023
$320hour
50ft Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

New
$425hour
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

4.5
$275-$375night
Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD
Sailing in Rock Hall · 4 guests

Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

5.0
$150hour
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
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
Superowner
$150hour
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
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
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
Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!
Sailing in Annapolis · 4 guests

Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!

5.0
$150hour
Robbins Chesapeake 40' Fishing Charters in Maryland
Fishing in Annapolis · 6 guests

Robbins Chesapeake 40' Fishing Charters in Maryland

5.0
$125-$150hour
Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland
Sailing in Saint Michaels · 6 guests

Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland

5.0
$250-$349hour
Sunset Champagne Cruise on the Chesapeake Bay
Sailing in Saint Michaels · 6 guests

Sunset Champagne Cruise on the Chesapeake Bay

New
$55person

Chester Reviews

  1. AA
    Andy
    Luxury yacht with Captain for 8 passengers to your Annapolis waterways

    My family had a wonderful afternoon cruise around Annapolis with Captain McCoy. He's incredibly nice, safety conscious, and a good communicator. His boat was spotless and well maintained. We enjoyed listening to our playlist as we toured Spa Creek, Eastport, the Severn River, and the City Dock. I would hire him again in a heartbeat!

  2. RR
    Reggie
    Luxury yacht with Captain for 8 passengers to your Annapolis waterways

    Was a great experience!! Me and the family loved every moment. Sometimes it’s the little things in life that makes you feel alive. The water gives you a sense of life and freedom from the everyday hustle and bustle. I will be booking with Mr. McCoy again soon-true example of professionalism.

  3. MF
    Melissa
    Luxury yacht with Captain for 8 passengers to your Annapolis waterways

    One of the best boating experiences ever! Keith was punctual, responsive, courteous, and really gave us a wedding anniversary outing to remember. Would absolutely book with him and again and look forward to our next trip! My husband and I had an amazing time!! Thanks again!

  4. Taylor
    Taylor
    Luxury yacht with Captain for 8 passengers to your Annapolis waterways

    My boating experience with Captain Keith was absolutely a 10/10. After booking, Keith provided details on what time my guests and I needed to arrive, an exact location of where we were to meet and a personal phone number to reach out once we arrived. I booked a 3 hour cruise, received a great rate and all of my guests had a great time cruising down the river. Keith was very accommodating and gave us full access to the boat which was very spacious for the 7 of us. All areas of the boat were very clean and comfortable and even allowed us to play our own music via Bluetooth. I will be booking again. Definitely book!!!!

  5. JR
    Josh
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Highly highly recommended! The boat is as advertised, but the real treat is spending time with Captain Alberto, and his wife Grace, who are such warm, loving, and knowledgeable people. They clearly know their boat inside and out, so you will never feel uncomfortable. But they also encourage guests to help running the boat and they have the knowledge to help everyone understand what is happening. Most importantly, they are simply fun to be around and a joy to talk to. I can't wait to sail with them again!

  6. BC
    Brian
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Across the board, a wonderful charter that exceeded expectations. It'd been some years since my wife and I had been on the water and what we expected was a day out refamiliarizing ourselves and just enjoying the Bay -- But Capt Alberto skillfully combined pleasurable sailing with private sailing lessons, a naval architecture primer, and boat buying 101. We can't wait to get back out on the water again with Alberto!