Rent the best Chestertown boat rentals of 2024
Top Chestertown Boat Rentals and Yacht Charters
$120+
/hour
Glen Burnie, MD
Tahoe T16: Your Ticket to Fun on the Water!
Annapolis, MD
20ft Fishing/Crabbing/Pleasure Craft
Annapolis, MD
Sailing Charter - Sunset Cruises, Learn to Sail, and Family Fun Time!
Arnold, MD
20' Regal Great for cruising & relaxing
Oxford, MD
2013 20' Sweetwater Sunrise Pontoon - Oxford - Tred Avon in comfort
Easton, MD
Explore the Eastern Shore on a 16' Boston Whaler Dauntless
$190+
/hour
Grasonville, MD
Fun 27' Bow Rider. Great for Water Tubing!
$56+
/hour
Edgewater, MD
"Equinox" - Center of the Sun - Lippincott 30'
$74+
/hour
Centreville, MD
Family Fun on the water (With Delivery)
Edgewater, MD
Center Console built for enjoying the Bay
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Stevensville, MD
Fun and Sporty 20' Sea Hunt 207 Triton
Essex, MD
Beautiful captained yacht on Middle River
Riviera Beach, MD
19’ Carolina Skiff for Fishing and Cruising! Available all year!
Edgewater, MD
Excellent Chesapeake sailing onboard Windsnap
Annapolis, MD
Come take a cruise on the Annapolis Jet Boat
How to rent a boat in Chestertown?
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.
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Got questions?
Frequently asked questions
What makes Boatsetter different from other boat rental platforms?
What makes Boatsetter different is peace of mind. Boatsetter is the first and only boat rental marketplace to offer insurance on every peer-to-peer boat rental. We know choosing the right boat rental platform is essential to your experience 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.
How to rent a boat on Boatsetter?
At Boatsetter, our mission is to make getting out on the water as easy as possible. With our intuitive booking system, you can rent a boat as soon as today.
-First, you must determine your budget and the type of boat you want to rent.
-Next, decide where you would like to boat and the kind of boat you would like to spend the day on.
-Finally, determine if you will be needing a boat captain and reach out to the boat owner.
That’s it! You’re officially on your way to a fantastic day out on the water.
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 much does it cost to rent a yacht?
The cost of renting a yacht depends on the boat’s size and the amount of time you’ll use the yacht. The onboard amenities and luxurious accommodations also dictate the price. You can contact our yacht specialists for a custom quote by visiting https://www.boatsetter.com/luxury-yacht-charters.
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.
Can you rent a yacht for the day?
Boatsetter allows you to rent a yacht for the day. Single-day yacht rentals are available for a select number of yachts. To chat with a yacht specialist please visit https://www.boatsetter.com/luxury-yacht-charters.
Can you rent a yacht for the week?
Boatsetter allows its customers to rent a yacht for the week. Renting a yacht for a week gives you more access to the wide range of yachts available on our platform. You can either book a rental directly through the site or connect with one of our charter specialists to plan your trip here: https://www.boatsetter.com/luxury-yacht-charters.
Can you rent a yacht for the month?
Booking a month-long yacht rental is a detailed and hands-off process when working with our team of yacht charter specialists. We tailor each yacht charter to our client's specific wants and needs. Our luxury yacht charter specialists can be reached at (954) 715-4114 or by visiting https://www.boatsetter.com/luxury-yacht-charters.
How to rent a private yacht?
Renting a private yacht is a very detailed experience that caters to your exact needs while onboard one of our luxury yachts. To plan your private yacht rentals experience please visit https://www.boatsetter.com/luxury-yacht-charters.
How much does it cost to rent a pontoon boat?
The cost of renting a pontoon boat depends on the size, location, and rental time of the boat. Prices can range anywhere from $200 for a half-day rental or just under a $1,000 for longer rentals.
How much does it cost to charter a yacht?
The cost to charter a yacht varies depending on the boat size and the length of the charter. Prices typically range from less than $1,000 to $5,000 plus if you’re wanting to charter the yacht overnight.
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.
How does the boat insurance work?
Boat insurance typically covers loss caused by things such as fire, sinking, storms, and collisions. The extent of the coverage varies depending on the policy.
Do I need my own insurance to rent a boat?
You do not need boat insurance when renting with Boatsetter. Coverage is provided under the Peer-to-Peer Boat Rental Policy, which is underwritten by GEICO Marine Insurance Company. The policy was written from the ground up as a stand-alone recreational boat rental insurance policy covering the period of time that the boat is being rented and is available for all non-commercially insured boats.
Does Boatsetter screen renters?
Yes. We use a system called Cognito to ensure that payment information matches the renter's identity. We also require renters taking out a captained boat to be at least 18 years old and on a bareboat to be at least 25 years old.
Is listing my boat on Boatsetter free?
Yes! Listing a boat is completely free. We only take a commission when your boat is rented. We only make money when you do!
What if I'm not comfortable having a renter drive my boat?
If you are not comfortable having a renter drive your boat, we have an expansive network of licensed and experienced captains. Once your boat is listed, you can filter through our network of captains and favorite captains in your area that you would like to operate your boat.
Top destinations for boat rentals
Top boat rentals reviews in Chestertown, MD
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5/5 stars
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5/5 stars
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5/5 stars
Taylor
Aug 2024 -
5/5 stars
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5/5 stars
Great time on the water, appreciate your facilitating
Jesse
Aug 2024 -
5/5 stars
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5/5 stars
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5/5 stars
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5/5 stars
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5/5 stars
Great family experience. Thank you Sunmi!!!!
Priscilla
Aug 2024 -
5/5 stars
Clean, comfortable boat, right on time, very fair price and knowledgeable, friendly captain. Book this one!
Tony
Aug 2024 -
5/5 stars
What an amazing day! The boat was fantastic -- spacious fast and Adam the owner was communicative and helpful!
Geoffrey
Aug 2024
Own a boat?
Boatsetter lets you make money renting out your boat. Peace of mind and insurance is included in every rental, and you choose who rents your boat.
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