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Browse Maryland Boat Rentals.

Page 3 of 7162 listings

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
Chaparral 350 Signature Motor Yacht Rental in Washington, District of Columbia
Events in Washington · 9 guests

Chaparral 350 Signature Motor Yacht Rental in Washington, District of Columbia

5.0
$350hour
$450HR | +13 People | Double Deckers Boat
Events in Washington · 13 guests

$450HR | +13 People | Double Deckers Boat

5.0
Superowner
$450hour
$300hr|12 people| Luxury Yacht
Events in Washington · 12 guests

$300hr|12 people| Luxury Yacht

5.0
Superowner
$350hour
Bluewater Coastal Cruiser 50ft for Entertaining in Washington, DC
Events in Washington · 13 guests

Bluewater Coastal Cruiser 50ft for Entertaining in Washington, DC

4.9
$350-$390hour
Maxum 2400 SE (26 feet) with captain in Washington DC ready to serve you!
Powerboats in Washington · 6 guests

Maxum 2400 SE (26 feet) with captain in Washington DC ready to serve you!

5.0
$200hour
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
Charter the 34ft Sundancer Motor Yacht in Washington,  DC
Events in Washington · 8 guests

Charter the 34ft Sundancer Motor Yacht in Washington, DC

5.0
$250hour
2021 24' Sylvan L3 DLZ Pontoon Boat
Powerboats in Riviera Beach · 12 guests

2021 24' Sylvan L3 DLZ Pontoon Boat

5.0
$149hour
$300 per hour | 8 PPl | Water Activity + Grill BBQ | Monterey 322 Cruiser
Events in Washington · 8 guests

$300 per hour | 8 PPl | Water Activity + Grill BBQ | Monterey 322 Cruiser

5.0
Superowner
$300hour
One Love Smoothie Cafe Morning Assateague Cruise
Powerboats in Ocean City · 6 guests

One Love Smoothie Cafe Morning Assateague Cruise

New
$35person
Bayliner Cruising Boat for 6 People in Washington, DC
Events in Arlington · 6 guests

Bayliner Cruising Boat for 6 People in Washington, DC

5.0
$200hour
Perfect Party Boat Rental In Potomac River, Washington
Events in Washington · 8 guests

Perfect Party Boat Rental In Potomac River, Washington

5.0
$275hour
The Innamorata... Most Elegant, Historic Yacht on the Potomac!
Events in Washington · 12 guests

The Innamorata... Most Elegant, Historic Yacht on the Potomac!

5.0
$290-$390hour
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

New
$325hour
50ft Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

New
$400hour
"Airbow "- Cruise the Potomac in Luxury
Events in Washington · 13 guests

"Airbow "- Cruise the Potomac in Luxury

New
$570hour
23ft Odyssey Pontoon Rental in Washington, District of Columbia
Powerboats in Washington · 12 guests

23ft Odyssey Pontoon Rental in Washington, District of Columbia

5.0
$250-$1,000day
50' Sea Ray 470 Luxury Sport Yacht for rent in Washington, DC
Events in Washington · 10 guests

50' Sea Ray 470 Luxury Sport Yacht for rent in Washington, DC

5.0
$550hour
Rent this 300 Sea Ray Cuddy Cabin Cruiser in Washington, DC
Powerboats in Washington · 6 guests

Rent this 300 Sea Ray Cuddy Cabin Cruiser in Washington, DC

5.0
$155hour
Luxurious Silverton 35ft Convertible Motor Yacht in Washington, DC
Events in Washington · 12 guests

Luxurious Silverton 35ft Convertible Motor Yacht in Washington, DC

5.0
$499hour
Rinker Captiva Bowrider Rental in Washington, District of Columbia
Powerboats in Washington · 6 guests

Rinker Captiva Bowrider Rental in Washington, District of Columbia

5.0
$150hour
Welcraft 260 SE 30ft Yacht Charter in Washington
Events in Washington · 6 guests

Welcraft 260 SE 30ft Yacht Charter in Washington

5.0
$160hour
Fully Crewed Annapolis Sailing Cruises
Sailing in Annapolis · 6 guests

Fully Crewed Annapolis Sailing Cruises

New
$175person

Maryland Reviews

  1. George

    George

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

    Great value! Excellent sailing gear!! If you are an experienced sailor with at least one other person, you won't find a better value for day or overnight sailing near Annapolis. I will definitely be renting this boat again either with my family for the day or some buddies overnight. Took Icarus on a two night late-October trip from Rock Hall, overnight in Annapolis then St. Michaels with a couple buddies. James made the process VERY easy - very communicative and willing to go the extra mile for our convenience. This Hunter 34 sails really well (especially upwind.) It is set up that one experienced sailor and one other person can easily manage it. Comfort-wise it is probably better dockside on shore power in order to be able to utilize the cabin climate control system and power outlets for charging your phones (bring portable chargers if you won't be on shore power.) Returning the boat into the slip was a little tricky and James offered to be there to "coach us" in but we managed it on our own. The diesel was very reliable and fuel efficient - recommend you listen very carefully to James when he explains how to start it because can be a little tricky (as of Oct 2023.) Recommend you bring a handheld (or phone) GPS because as of Oct 23 the GPS is in the cabin. Bottom line - this is a great value - don't hesitate to book!!

  2. Janessa

    Janessa

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

    We had a wonderful experience chartering Jim’s sailboat over Labor Day weekend. Jim was very accommodating, walking through the boat with us and making sure everything was in great shape before we began our charter. We sailed from Rock Hall to Annapolis and back, spending two nights aboard Icarus. His upgrades to the boat really helped make it easier to sail and more comfortable to relax in, and Jim was always readily available if we had any questions. Could not recommend this more highly, and we don’t think there’s a better charter out there for the price in the Chesapeake.

  3. JM

    John

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

    Jim’s boat is an amazing sailing set up for those looking for a great way to explore the Bay. The boat is equipped with everything you’ll need for a day sail or an overnight as my wife and I did. It was a great boat to explore the Bay with and Jim gave us great recommendations on where to anchor out!

  4. BH

    Brack

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

    The boat is older but everything works. It has been well maintained and sails very well, with one owner only. Controls and lines are simple and straightforward. The owner was very responsive and helpful, including suggestions on destinations. The location is great, 10 feet from our car to the boat.

  5. Mark

    Mark

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

    Icarus is an older boat that shows it age a bit, but the rig was easy to sail and all of the equipment worked well. It was our first overnight charter and I was not disappointed at all. We had perfect weather and enjoyed our sail from/to Annapolis taking about 4 hours each way. Jim gave great advice and his communication was excellent prior to and during our charter. Absolutely no complaints.

  6. Travis

    Travis

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

    This 34' Hunter is comfortable, clean, fun to sail, and has excellent sleeping accommodations. We had a great sail across the Chesapeake bay in 3-4' waves and felt safe and secure the entire time. You will not be disappointed with this charter. James (the boat owner) is a class act and will always go the extra mile to make your charter experience unforgettable. If you're considering a charter on the Chesapeake, this is the boat for you! I hope to see you next year, James!