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    Browse Annapolis Boat Rentals

    5.0
    (601 Reviews)

    Page 2 of 2 • 44 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    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
    $375/hour
    Relaxing Excitement of the Chesapeake Bay and tributaries on our Yacht
    Events in Annapolis · 6 guests

    Relaxing Excitement of the Chesapeake Bay and tributaries on our Yacht

    New
    $300/hour
    Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland
    Events in North Beach · 8 guests

    Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland

    5.0
    $400/hour
    DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!
    Sailing in Annapolis · 10 guests

    DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!

    New
    $232+/hour
    50′ VIKING - Your Chartered Experience Awaits!
    Events in Annapolis · 12 guests

    50′ VIKING - Your Chartered Experience Awaits!

    New
    $841+/hour
    Come take a cruise on the Annapolis Jet Boat
    Powerboats in Kent Narrows · 11 guests

    Come take a cruise on the Annapolis Jet Boat

    New
    $360/hour
    19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake
    Powerboats in Annapolis · 6 guests

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

    New
    $125+/hour
    19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake
    Powerboats in Annapolis · 6 guests

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

    New
    $125+/hour
    26’ CREST TRITOON | Excellent Pontoon | Seats 12
    Powerboats in Annapolis · 12 guests

    26’ CREST TRITOON | Excellent Pontoon | Seats 12

    New
    $194+/hour
    Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape
    Sailing in Annapolis · 13 guests

    Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape

    New
    $350+/hour
    Maxum 30ft Yacht! Escape for a day on the Chesapeake
    Events in Selby-on-the-Bay · 6 guests

    Maxum 30ft Yacht! Escape for a day on the Chesapeake

    New
    $280/hour
    19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake
    Powerboats in Annapolis · 6 guests

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

    New
    $125+/hour
    Enjoy the best views of Annapolis, MD aboard this beautiful Lydia dinner yacht
    Events in Annapolis · 128 guests

    Enjoy the best views of Annapolis, MD aboard this beautiful Lydia dinner yacht

    5.0
    $480+/hour
    21′ KENCRAFT | Center Console | Located On The South River
    Powerboats in Annapolis · 6 guests

    21′ KENCRAFT | Center Console | Located On The South River

    New
    $125+/hour
    46′ CARMEN | Take Everybody With You! | Captain Included
    Events in Annapolis · 30 guests

    46′ CARMEN | Take Everybody With You! | Captain Included

    New
    $670+/hour
    VIKO S 35 Sailboat in Deale
    Sailing in Deale · 6 guests

    VIKO S 35 Sailboat in Deale

    New
    $298/hour
    VIKO 30 Premium Sailing Yacht In Deale, MD
    Sailing in Deale · 5 guests

    VIKO 30 Premium Sailing Yacht In Deale, MD

    New
    $925/day
    34ft Sailing Yacht in Annapolis, Maryland
    Sailing in Annapolis · 4 guests

    34ft Sailing Yacht in Annapolis, Maryland

    New
    $250/hour
    30' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 6 Guests Capacity
    Powerboats in Annapolis · 6 guests

    30' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 6 Guests Capacity

    New
    Snoozed - Active 25 Aug 2026
    45' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 32 Guests Capacity
    Powerboats in Annapolis · 32 guests

    45' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 32 Guests Capacity

    New
    Snoozed - Active 25 Aug 2026

    Top Destinations Nearby

    Annapolis Reviews

    1. JA

      Joey

      Enjoy the best views of Annapolis, MD aboard this beautiful Lydia dinner yacht

      Booked a private yacht charter along the Island Princess for 3 hours and had a great experience! Captain Steve was kind, accommodating, and knowledgeable during our journey! Would 100% recommend! Thank you!

    2. Teresa

      Teresa

      Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland

      We loved it, had a great time. Will definitely go again!

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