What are the steps needed to rent a boat in Chesapeake City?

Find the best boat rentals in Chesapeake City

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Top Chesapeake City Boat Rentals and Yacht Charters

$166+ /hour

Pasadena, MD

5.0 (22 bookings)

Still Crazy II - Cruise the Chesapeake in luxury! (Captained)

3 - 8 hours Captained

Up to 10 passengers

$100+ /hour

Arnold, MD

4.9 (297 bookings)

20' Regal Great for cruising & relaxing

2 - 8 hours No captain

Up to 6 passengers

Rent a Sailfish motor yacht in Grasonville, MD near me

$186+ /hour

Grasonville, MD

5.0 (6 bookings)

Fun 27' Bow Rider. Great for Water Tubing!

3 - 8 hours Captained

Up to 10 passengers

$133+ /hour

Arnold, MD

4.9 (56 bookings)

29' Sea Ray Sundancer

2 - 8 hours No captain

Up to 8 passengers

$125+ /hour

Centreville, MD

Delivery Available - Sundance Boat

2 - 8 hours No captain

Up to 8 passengers

$144+ /hour

Middle River, MD

5.0 (5 bookings)

Swim, Fish, Cruise, Tube, Dock Hop Fun!!

2 - 8 hours Captained

Up to 6 passengers

$195+ /hour

Essex, MD

5.0 (1 booking)

Sail Away on Optimystic

2 - 8 hours Captained

Up to 6 passengers

Rent a PRO-LINE BOATS center console in Pasadena, MD near me

$75+ /hour

Pasadena, MD

24’ Center Console – Quiet Yamaha Power | Cruise or Fish Pasadena, MD

2 - 8 hours Captain optional

Up to 12 passengers

$228+ /hour

Arnold, MD

38ft Regal

4 - 8 hours Captained

Up to 12 passengers

$231+ /hour

Chester, MD

2021 Avalon Catalina platinum twin 350 verados

6 - 8 hours Captained

Up to 8 passengers

$75+ /hour

Pasadena, MD

5.0 (10 bookings)

24ft Proline

2 - 8 hours No captain

Up to 12 passengers

$192+ /hour

Essex, MD

5.0 (2 bookings)

Beautiful captained yacht on Middle River

2 - 8 hours Captained

Up to 6 passengers

Rent a Fountaine Pajot catamaran in Annapolis, MD near me

$334+ /hour

Annapolis, MD

2018 Fountaine Pajot Helia 44

4 - 8 hours Captain optional

Up to 12 passengers

$296+ /hour

Baltimore, MD

Isabela

4 - 8 hours Captained

Up to 10 passengers

$74+ /hour

Centreville, MD

5.0 (17 bookings)

Family Fun on the water (With Delivery)

Pasadena, MD

The Pasadena Sea Cruiser

3 - 8 hours No captain

Up to 9 passengers

$283+ /hour

Camden, NJ

Enjoy the bar or sunpad on our luxury pontoon boat

2 - 4 hours Captained

Up to 6 passengers

$92+ /hour

Chestertown, MD

5.0 (3 bookings)

Ski boat with wakeboard tower

2 - 8 hours No captain

Up to 8 passengers

Top boat rentals reviews in Chesapeake City, MD

281,160

Customers Reviews

4.95

Avg. Rating

5/5 stars

Swim, Fish,...

This boat was exactly what we hoped it would be. Don't hesitate to book!

Jesse

Jun 2025
5/5 stars

20' Regal Great...

Mike’s boat is in fantastic shape and he’s located right off of the Chesapeake Bay so it’s super easy to get there....

Annie

May 2025
5/5 stars

Fun 27' Bow...

Beautiful boat, and just a super fun experience - would absolutely love to take it out again! Adam was even there to...

Meghan

May 2025
5/5 stars

20' Regal Great...

Mike was awesome. Would totally book again!

Luke

May 2025
5/5 stars

Still Crazy II -...

Absolutely terrific captain and vote! I wouldn’t hesitate to hire him again. Extremely professional and personable.M

Bill

May 2025
5/5 stars

Still Crazy II -...

Beautiful, smooth rising vessel! Comfortably seats everyone and excellent sound system.

Zachary

May 2025
5/5 stars

20' Regal Great...

Mike was super helpful and his boat was in great shape! We had the best day!

Annie

May 2025
5/5 stars

Still Crazy II -...

What a beautiful boat to cruise the Chesapeake in — it was spotless and super fun to entertain in. We had a group of...

Lindsey

Apr 2025
5/5 stars

Still Crazy II -...

Boat was excellent condition. Very nice and clean! It was pouring but when it cleared up, boat was very nice and...

Yesenia

Apr 2025
5/5 stars

Still Crazy II -...

Such a great experience. The boat was perfect for our days on the water and the crew was very accommodating and...

Joel

Oct 2024
5/5 stars

Still Crazy II -...

The boat was incredible and Will was graceful and helpful. Indie was an incredible dockmaster. We would absolutely...

Leon

Oct 2024
5/5 stars

Ski boat with...

Jamie

Sep 2024

How to rent a boat in Chesapeake City?

Find the perfect boat

Enter your desired location and date to explore our fleet of boats.

Select a captain

Choose to drive yourself or select a USCG licensed captain.

Book with ease

Connect with your boat owner and complete your booking online.

Set sail

Enjoy your day on the water with friends and family!

Why Boatsetter?

As the global leader in peer-to-peer boat rentals, Boatsetter offers an easy, safe and accessible way to experience on-the-water adventure. With boat rentals in 600+ locations, finding a boat is easy and with the option to tap into the largest network of USCG licensed captains, boating experience is not required.

Get out on the water worry-free, knowing our insurance covers every boating trip

Choosing the right boat rental platform is essential to your peace of mind while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

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Got questions?

Frequently asked questions

How much does it cost to rent a boat?

The cost to rent a boat depends on whether you are renting for a half-day or a full day, the boat features and the boat size can impact your boat rental price. Rental prices can range from $200 to $1,000 plus depending on the boat rental itself and the length of time of the rental.

How many people can fit on the boat rental?

The number of people who can fit on boat rental largely depends on the boat’s size and how many life jackets are on board. Currently the coast guard allows a maximum of 10-12 people on a Boatsetter boat rental.

How old do you have to be to rent a boat?

You must be 18 years old to rent a captained boat and 25 years old if you would like to rent a bareboat charter.

Do I need a boating license to rent a boat?

Boating license requirements vary from state to state. As a renter, you are responsible for understanding local state requirements.

How much does it cost to rent a boat for the day?

The cost of renting a boat for the day on average ranges from $200 to $1200. The cost to rent a boat varies depending on the size of the boat and the length of time that you will be using the boat.