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Browse Annapolis Boat Rentals

Page 2 of 239 listings

30ft Bowrider! Enjoy a day on the water around the Chesapeake Bay in Maryland!
Powerboats in Annapolis · 8 guests

30ft Bowrider! Enjoy a day on the water around the Chesapeake Bay in Maryland!

3.7
Snoozed - Active 02 Jan 2025
Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland
Sailing in Saint Michaels · 6 guests

Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland

5.0
$250-$349hour
Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD
Sailing in Rock Hall · 4 guests

Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

5.0
$150hour
32' Center Console - up to 6 Guests from Stevensville, MD
Powerboats in Stevensville · 6 guests

32' Center Console - up to 6 Guests from Stevensville, MD

5.0
$375hour
Historical Annapolis Private Boat Cruise onboard a beautiful Swift Trawler!
Events in Annapolis · 6 guests

Historical Annapolis Private Boat Cruise onboard a beautiful Swift Trawler!

5.0
Snoozed - Active 02 Jun 2024
Pershing 65 Power Mega Yacht Rental in Stevensville, Maryland
Events in Stevensville · 6 guests

Pershing 65 Power Mega Yacht Rental in Stevensville, Maryland

New
$550hour
Sea Doo Switch - Sea Cruiser Pontoon in Pasadena MD
Powerboats in Riviera Beach · 11 guests

Sea Doo Switch - Sea Cruiser Pontoon in Pasadena MD

New
$150hour
Enjoy a Day on the Bay and Cruise the South River
Powerboats in Annapolis · 6 guests

Enjoy a Day on the Bay and Cruise the South River

New
$130-$150hour
Sunset Champagne Cruise on the Chesapeake Bay
Sailing in Saint Michaels · 6 guests

Sunset Champagne Cruise on the Chesapeake Bay

New
$55person
You don't have to own a boat to enjoy one.
Powerboats in Annapolis · 7 guests

You don't have to own a boat to enjoy one.

New
Snoozed - Active 02 May 2024
Catalina 445 Sailboat
Sailing in Deale · 6 guests

Catalina 445 Sailboat

New
$298hour
 VIKO S 35 Sailboat in Deale
Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New
$298hour
Pristine Hooligan Departs from a Private Pier with a Captain and Fuel INCLUDED
Powerboats in Annapolis · 5 guests

Pristine Hooligan Departs from a Private Pier with a Captain and Fuel INCLUDED

New
$200hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$300hour
Bentley 220 Cruise Pontoon for rent in Edgewater
Powerboats in Edgewater · 10 guests

Bentley 220 Cruise Pontoon for rent in Edgewater

New
$400hour

Annapolis Reviews

  1. Pamela

    Pamela

    Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland

    We booked this experience for my husbands birthday and it was PERFECT! The Selina II IS STUNNING, and Captain Iris and her crew were absolutely wonderful. Captain Matt was fantastic! He took such good care of us while we sailed across the Chesapeake Bay and celebrated with a couple of glasses of delicious champagne! Look no further and book the Selina II, you won’t regret it, it’s absolutely worth it !!

  2. IP

    Irene

    Historical Annapolis Private Boat Cruise onboard a beautiful Swift Trawler!

    Luis is customer service friendly business owner. He helped to make my birthday celebration with friends very special. He took pictures for us and with us. Highly recommend using his yacht for a cruise 🛳.

  3. MP

    Mohan

    Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

    Captain Rob made the trip memorable with the beautiful views of the Chesapeake sunset and anecdotes of the area and his marine career.

  4. KA

    Karen

    30ft Bowrider! Enjoy a day on the water around the Chesapeake Bay in Maryland!

    Quentin was excellent. Friendly and a great captain.