Cookies!

We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.

Map View

Browse Annapolis Boat Rentals

5.0

(574 Reviews)

Page 1 of 3 • 55 listings

Powerboats in Severna Park · 12 guests

Pro line Center Console Magothy River - Perfect for fishing exploring cruising

5.0

$65+/hour

Instant Book

Events in Selby-on-the-Bay · 10 guests

Private Yacht Charter: On 40ft Regal Commodore

5.0

$300/hour

Powerboats in Annapolis · 8 guests

2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

4.9

Best of 2025

$225/hour

Sailing in Annapolis · 12 guests

JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!

5.0

$250+/hour

Powerboats in Severna Park · 4 guests

2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

5.0

$120/hour

Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0

Superowner

$138+/hour

Instant Book

Events in Annapolis · 8 guests

Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

5.0

$250/hour

Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

5.0

$325/hour

Sailing in Annapolis · 12 guests

SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

5.0

$400+/hour

Events in Deale · 10 guests

Luxurious 51’ SeaRay Flybridge Yacht With Twin 600 Hp Cummins Engine

5.0

$500/hour

Sailing in Rock Hall · 6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

5.0

$150/hour

Sailing in Mayo · 6 guests

Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.

5.0

$175+/hour

Powerboats in Annapolis · 6 guests

19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake

New

$125+/hour

Powerboats in Annapolis · 6 guests

Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis

4.8

$95+/hour

Instant Book

Sailing in Annapolis · 13 guests

STARZ -Lagoon 42 Catamaran in Chesapeake Bay

5.0

$400+/hour

Sailing in Rock Hall · 4 guests

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

4.6

$275+/night

Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0

$250+/hour

Instant Book

Powerboats in Annapolis · 12 guests

26′ BENNINGTON PONTOON | Adventure Awaits | Seats 12

5.0

$194+/hour

Powerboats in Edgewater · 6 guests

Chaparral SSX 27ft - Captained Private Charter - Watersports Included!!

5.0

$225/hour

Instant Book

Events in Selby-on-the-Bay · 8 guests

43ft Cruiser Express Yacht for Daily Charter

5.0

$400/hour

Powerboats in Deale · 6 guests

COME CRUISE THE BEAUTIFUL CHESAPEAKE BAY!

5.0

$200/hour

Sailing in Annapolis · 12 guests

SLOWDOWN - DUFOUR 430

New

$250+/hour

Sailing in Edgewater · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0

$425/hour

Events in Annapolis · 12 guests

50′ VIKING - Your Chartered Experience Awaits!

New

$841+/hour

Top Destinations Nearby

Annapolis Reviews

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
LC
Laura

2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island
Amazing! I went with my family, ages 5 and up, and everyone had a fantastic time. Captain Dushaune is a gem - personable, patient, funny, prepared. His boat is beautiful and well maintained. He was laid back while also keeping us safe and happy. He knew the waterways well, took us to a perfect cove for swimming and relaxing. The marina where his boat is located is ideal - clean, easy parking, great views, great water access. I cannot wait to book with him again. Highest possible recommendation!
Marie

38-ft Hunter 376 Sailing Adventure in Annapolis
We thoroughly enjoyed our time with Alberto and his wife, Grace. Alberto is a delight to sail with - we learned so much from him. Grace is so lovely and gracious. We sailed around Annapolis during Memorial Day weekend and the weather was perfect. Alberto was very accommodating and friendly. We hope to see you again soon!
JC
John

Pro line Center Console Magothy River - Perfect for fishing exploring cruising
Robert is a great host and provided us with an awsome experience. Boat was very good for our 4 hour trip around the bay and handled the rough weather that kicked up with no problem. We had 5 adults and a dog.
Sam

38-ft Hunter 376 Sailing Adventure in Annapolis
Captain Alberto is a wonderful Captain. Handles the boat with an expert confidence and was also a willing and kind teacher to my two kids who had millions of questions.
David

Pro line Center Console Magothy River - Perfect for fishing exploring cruising
Couldn’t have asked for a better experience with Robert (Scott)! He was so nice to me and my family, the boat was wonderful, and my family had an absolutely wonderful time on the water. He was super flexible, helped us get underway, and get back to the dock at the end of the day. His trustworthiness and kindness didn’t go unnoticed. Couldn’t recommend him enough to others and hope to rent from him again soon!