Find the best Annapolis, MD Boat Rentals and Yacht Charters Near You

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Top Annapolis, MD Boat Rentals and Yacht Charters

Rent a Carolina Skiff center console in Riviera Beach, MD near me
$50+ /hour

Riviera Beach, MD

5.0 (16 bookings)

19’ Carolina Skiff for Fishing and Cruising! Available all year!

2 - 8 hours No captain
Up to 5 passengers
Rent a Catamaran catamaran in Annapolis, MD near me
Icon $831+ /hour

Annapolis, MD

5.0 (18 bookings)

54' Luxury Yacht – Perfect for Family, Friends & Business Outings

3 - 8 hours Captained
Up to 12 passengers
Rent a Pro-Line Boats center console in Pasadena, MD near me
Icon $105+ /hour

Pasadena, MD

5.0 (23 bookings)

24ft Proline

2 - 8 hours No captain
Up to 12 passengers
Rent a 28 whaler outrage center console in Chester, MD near me
Icon $150+ /hour

Chester, MD

5.0 (6 bookings)

28 Boston Whaler Outrage, safe and comfortable for fishing or cruising

2 - 8 hours Captain optional
Up to 8 passengers
Rent a YAMAHA bow rider in Annapolis, MD near me
$125+ /hour

Annapolis, MD

5.0 (17 bookings)

Yamaha SX210 Bow Rider Twin Jet Engine Boat

2 - 8 hours Captained
Up to 6 passengers
Rent a GRADY-WHITE BOATS cuddy cabin in Severna Park, MD near me
$69+ /hour

Severna Park, MD

Grady White

2 - 8 hours No captain
Up to 6 passengers
Rent a Lydia commercial in Annapolis, MD near me
$413+ /hour

Annapolis, MD

Enjoy the best views of Annapolis aboard the Island Princess

2 - 8 hours Captained
Up to 128 passengers
Rent a Stratos Boats fish and ski in Annapolis, MD near me
$97+ /hour

Annapolis, MD

5.0 (28 bookings)

Stratos walkaround fishing boat

3 - 8 hours No captain
Up to 6 passengers
Rent a Regal Boats bow rider in Arnold, MD near me
$100+ /hour

Arnold, MD

4.9 (307 bookings)

20' Regal Great for cruising & relaxing

2 - 8 hours No captain
Up to 6 passengers
Rent a Cruisers Yachts cruiser in Edgewater, MD near me
$366+ /hour

Edgewater, MD

5.0 (5 bookings)

Express Yacht Charters

2 - 8 hours Captained
Up to 8 passengers
Rent a Chaparral Boats bow rider in Edgewater, MD near me
$213+ /hour

Edgewater, MD

5.0 (15 bookings)

Chaparral 256 SSX

2 - 8 hours Captained
Up to 6 passengers
Rent a Jeanneau sloop in Annapolis, MD near me
$203+ /hour

Annapolis, MD

5.0 (9 bookings)

Sail away on the Chesapeake Bay with Chessie from Annapolis!⛵️

2 - 8 hours Captained
Up to 6 passengers
Rent a Kencraft Boats pilothouse in Edgewater, MD near me
$125+ /hour

Edgewater, MD

5.0 (1 booking)

Enjoy a relaxing day on the Chesapeake bay with Tight Times charters!

2 - 8 hours Captained
Up to 6 passengers
Rent a Catamaran Cruiser catamaran in Annapolis, MD near me
$397+ /hour

Annapolis, MD

5.0 (35 bookings)

46' Catamaran Charter with Water Toys - Annapolis, MD

3 - 8 hours Captained
Up to 12 passengers
Rent a Maxum express cruiser in Deale, MD near me
$181+ /hour

Deale, MD

5.0 (4 bookings)

Amazing boating experience on the Chesapeake Bay

2 - 4 hours Captained
Up to 6 passengers
Rent a Sea Fox center console in Edgewater, MD near me
$167+ /hour

Edgewater, MD

5.0 (19 bookings)

26’ Sea Fox w/ Restroom - Bachelor-ette Parties!!!

2 - 8 hours No captain
Up to 10 passengers
Rent a BENNINGTON MARINE pontoon in Annapolis, MD near me
$79+ /hour

Annapolis, MD

5.0 (84 bookings)

2017 Bennington 20SL Pontoon for Annapolis sightseeing in style!

6 - 8 hours Captain optional
Up to 9 passengers
Rent a REGAL BOATS motor yacht in Pasadena, MD near me
$178+ /hour

Pasadena, MD

5.0 (31 bookings)

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

3 - 8 hours Captained
Up to 6 passengers

Top boat rental reviews in Annapolis, MD

Verified full
300,617
Customers Reviews
4.95
Avg. Rating

  • We have rented this boat numerous times, and we keep coming back because the boat is very clean and in great shape. ...

    Doug

    Aug 2025

  • Tyler was awesome. The boat was super clean, stocked with water and we couldn't have asked for a better captain that...

    Jennifer

    Aug 2025

  • Michael

    Aug 2025

  • Great time celebrating my Wife's 40th out on the bay. Boat was clean and perfect for the family. Andy, the boat...

    cody

    Aug 2025

  • Captain Will was awesome. Would definitely be back.

    Owen

    Aug 2025

  • Great communication, service, accommodating. Highly recommend

    Shalin

    Aug 2025

  • Had a great time! Great boat and Mike’s always a pleasure to work with.

    Adam

    Aug 2025

  • Great experience renting this boat. Clean, well provisioned, just as described. Would definitely rent again.

    Rohit

    Aug 2025

  • Great boat!!! Super clean and pristine.

    Jeff

    Aug 2025

  • Working with Mike was an excellent experience from start to finish. He is very responsive, provided helpful...

    Brad

    Aug 2025

  • I can't say enough positive things about Captain Dave and his First Mate, Krystal. It was a reunion day with my...

    Joel

    Aug 2025

  • Beautiful boat! Maintained excellently, like new! A ton of space too for large groups

    Erin

    Aug 2025

How to rent a boat in Annapolis?

1

Find the perfect boat

Enter your desired location and date to explore our fleet of boat, Annapolis, MD, United Statess.

2

Select a captain

Choose to drive yourself or select a USCG licensed captain.

3

Book with ease

Connect with your boat owner and complete your booking online.

4

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.

Boating with Boatsetter

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.

Top destinations for boat rentals, Annapolis, MD, United States


Annapolis’ Most Popular Experiences

Given its history, you will soon begin to understand why Annapolis is the perfect place to sail. Here are a few of the things you can get up to by the water.

Join the fun at the Sailing Races
In the summer months, all of the action can be found at the weekly Wednesday sailing race. You can either spectate from the side or follow the action from aboard your Annapolis boat rental.

Get down to the Boat Shows
In the spring and fall months, you can check out the U.S.’s oldest boat shows. Spectators flock in their tens of thousands to check out what’s been shown. Take a wander around and think about what type of Annapolis boat rental you’ll be taking out the next morning.

Make Sure you Pack your Rod
Fishing is a must when out on the water in Annapolis. You’re bound to fill your bags with the likes of Redfish, black drum, spotted seatrout, as well as both smallmouth and largemouth bass.

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Annapolis Boat Rentals

Annapolis’ Best Bodies of Water

Enjoy the Severn River

The Severn River is a quiet body of water that makes for the ultimate place to unwind on your Annapolis boat rental. It’s home to a restored oyster reef which gives it an abundance of marine life, so have your rod at the ready.

Loop Around Kent Island

You’ll see Kent Island directly opposite the shoreline at Annapolis. Take your Annapolis boat rental around for a casual loop of the island and take in its sights. Given its size, it’s likely to be the first destination on your mind.

Sail Down South River

South River offers a pleasant place to explore in Annapolis. Its tranquil waters create a relaxing and peaceful aura whereby you can only hear your boat skim across the water. Once you reach this body of water, all of your worries will pass away.

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Boat rentals in Annapolis, MD



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