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The Best Cruising Catamaran Rentals in Chesapeake Bay
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Chesapeake Bay
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$110-$610
Sailboats
Set sail with these traditional wind-powered boats
$90-$1,065
Fishing Charters
Let a captain do the driving while you do the fishing
$60-$725
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$85-$755
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$35-$300
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$55-$470
Kayaks
Who says you need a motor to have fun on the water?
$80-$450
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$80-$400
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$95-$350
Whale Watching
See some of the ocean’s most incredible creatures with these eco tours
$60
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$150
Top Cruising Catamaran Rental Locations Near Chesapeake Bay
Hampton, Virginia
7 boats to rent
Virginia Beach, Virginia
17 boats to rent
Chesapeake, Virginia
28 boats to rent
Richmond, Virginia
10 boats to rent
Fort Washington, Maryland
9 boats to rent
Potomac River, United States
176 boats to rent
Lake Anna, Virginia
10 boats to rent
Annapolis, Maryland
45 boats to rent
Arlington, Virginia
24 boats to rent
Washington, District of Columbia
101 boats to rent
Cape May, New Jersey
7 boats to rent
Lake Gaston, United States
7 boats to rent
Wildwood, New Jersey
7 boats to rent
Baltimore, Maryland
39 boats to rent
Wake Forest, North Carolina
8 boats to rent
Falls Lake, North Carolina
7 boats to rent
Lacey Township, New Jersey
7 boats to rent
Berkeley Township, New Jersey
9 boats to rent
Recent Reviews in Chesapeake Bay
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!!!
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!
DC
Donte
New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
From start to finish, the entire experience was seamless and professional. There was zero chaos—everything ran like clockwork. The crew was exceptional: friendly, attentive, and incredibly knowledgeable about the Chesapeake Bay and Annapolis. The yacht itself was spotless and in pristine condition. From the moment we arrived, the crew went above and beyond—helping us load in, beautifully setting up our catering, keeping our group refreshed with drinks and snacks, and later packing up leftovers and loading them into our car. Every detail was handled with care. If you’re considering a yacht rental, don’t hesitate—this experience was truly top-notch. We’re already looking forward to booking again!
SH
Sophia
Charter 44' Orana Cruising Catamaran In Deale, Maryland
This trip was above and beyond ! The boat is spacious, beautiful, and comfortable. Everything was seamless and we spent a wonderful time sailing, swimming, and relaxing on the various parts of the boat.
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!
KM
Kevin
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Captain Rob and First Mate Jen were wonderful. Both were super friendly and attentive, which made for a relaxing trip. And the boat had more than enough room to fit our group of 9 comfortably.
Top Cruising Catamaran Rental Locations in the United States
Los Angeles, California
344 boats to rent
Miami, Florida
975 boats to rent
Honolulu, Hawaii
47 boats to rent
Dania Beach, Florida
230 boats to rent
Marina del Rey, California
130 boats to rent
Miami Beach, Florida
363 boats to rent
Fort Lauderdale, Florida
250 boats to rent
Charleston, South Carolina
127 boats to rent
Annapolis, Maryland
45 boats to rent
San Diego, California
109 boats to rent
Baltimore, Maryland
39 boats to rent
Tampa, Florida
416 boats to rent
Culver City, California
37 boats to rent
Saint Petersburg, Florida
266 boats to rent
San Francisco, California
73 boats to rent
Oakland, California
45 boats to rent
Long Beach, California
77 boats to rent
Palm Beach, Florida
148 boats to rent
How To Book on Getmyboat
Browse
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Inquire & Book
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Enjoy
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
Real reviews from happy Getmyboaters.
4.9 out of 5! 500,000+ reviews
