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The Best Boat Rentals Near Chester
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Chester
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$210-$930
Sailboats
Set sail with these traditional wind-powered boats
$145-$1,005
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$175-$600
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$230-$400
Fishing Charters
Let a captain do the driving while you do the fishing
$65-$600
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$65-$600
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$195
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$105
Top Boat Rental Locations Near Chester
Recent Reviews in Chester
ET
Eris
Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
This is everything you could want. Great boat and captain. McCoy has everything you need for a great trip. Plenty of space onboard for all your food and drink and all the toys you could want for a fun day on the water. We count thank him enough fro a such great experience and a great price! We will be booking again for sure!
AI
Amy
2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island
Dushaune was amazing! The best boat ride we have ever had. He is extremely nice and drove us to a swimming area that was amazing. We enjoyed just hanging in the water, talking with him. We lost track of time because we were having so much fun. Would definitely love to go on a ride with him 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!
HT
Hien
2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island
Dushaune is a great captain and great host, he is down to earth, knowledgeable, funny. We are a group of 6 with very different characters and age (from 7-50) but all of us had fun. We felt great after the ride. Thanks Dushaune. Highly recommended
GA
Giselle
38-ft Hunter 376 Sailing Adventure in Annapolis
Capt. Alberto and Graciela, the best! We had a great time and enjoyed learning about sailing with them. Everything was as described and much better. You’ll have a great time too! ⛵️☀️🩵
Ashraf
2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland
The whole experience was above and beyond the expectations the boat is tidy and clean and Sunmi is very helpful and knowledgeable. Elevate your experience and book this boat with Sunmi.
Top Boat Rental Locations in the United States
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!
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