Cookies & Agreements
By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.
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
$170-$800
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$120-$990
Sailboats
Set sail with these traditional wind-powered boats
$95-$810
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$150-$435
Fishing Charters
Let a captain do the driving while you do the fishing
$95-$840
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$95-$945
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$45-$390
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$210-$1,150
Kayaks
Who says you need a motor to have fun on the water?
$85-$195
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$150
Top Cruising Catamaran Rental Locations Near Chesapeake Bay
Virginia Beach, Virginia
17 boats to rent
Chesapeake, Virginia
29 boats to rent
Fort Washington, Maryland
13 boats to rent
Selby-on-the-Bay, Maryland
8 boats to rent
Potomac River, United States
165 boats to rent
Oxon Hill, Maryland
7 boats to rent
Lake Anna, Virginia
8 boats to rent
Annapolis, Maryland
53 boats to rent
Arlington, Virginia
31 boats to rent
Washington, District of Columbia
121 boats to rent
Cape May, New Jersey
11 boats to rent
Lake Gaston, United States
7 boats to rent
Wildwood, New Jersey
9 boats to rent
Baltimore, Maryland
50 boats to rent
Wake Forest, North Carolina
10 boats to rent
Falls Lake, North Carolina
8 boats to rent
Long Beach Island, New Jersey
8 boats to rent
Berkeley Township, New Jersey
7 boats to rent
Recent Reviews in Chesapeake Bay
EC
Emily
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Had a group with me and they had a blast. Weather started as misty and then became wonderfully sunny along the way. Hoping to see some sea life but alas none waves were pretty choppy. Boat was wonderful.
DC
David
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Our group of seven spent a fabulous half day with Captain Rob and Mate Dianna. Couldn't have been happier with the whole experience. Communication was quick and easy. On board, they were super friendly and engaging. The vessel itself was spotless and super comfortable as we hung out on the front "trampoline" area, sailing around the Bay. Thanks for such a fun adventure. We are already talking about a future engagement!
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!
Lauren
Charter 42' Lagoon Catamaran in Annapolis, MD
We had an amazing day on the bay with Captain Adam! He was super communicative leading up to the trip, providing amazing instruction to make it as easy as possible to get aboard. While on board the vessel was very clean and comfortable and he and his team were knowledgeable about the area. Highly recommend! They’re lovely!
Top Cruising Catamaran Rental Locations in the United States
Los Angeles, California
355 boats to rent
Miami, Florida
893 boats to rent
Honolulu, Hawaii
43 boats to rent
Miami Beach, Florida
316 boats to rent
Marina del Rey, California
125 boats to rent
Fort Lauderdale, Florida
185 boats to rent
Dania Beach, Florida
164 boats to rent
Charleston, South Carolina
131 boats to rent
Tampa, Florida
369 boats to rent
Annapolis, Maryland
53 boats to rent
Saint Petersburg, Florida
241 boats to rent
San Diego, California
106 boats to rent
Baltimore, Maryland
50 boats to rent
San Francisco, California
83 boats to rent
Oakland, California
50 boats to rent
Key West, Florida
36 boats to rent
Chicago, Illinois
286 boats to rent
Long Beach, California
86 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
