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    Oxford, Maryland Boat Rentals

    Page 1 of 1 • 24 listings

    Experience the Charm of St. Michaels Aboard the 41ft Sail Selina 2hr Boat Tour
    Sailing in Saint Michaels · 6 guests

    Experience the Charm of St. Michaels Aboard the 41ft Sail Selina 2hr Boat Tour

    New
    $350/hour
    Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours
    Sailing in Saint Michaels · 6 guests

    Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours

    New
    $400/hour
    Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail
    Sailing in Saint Michaels · 6 guests

    Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail

    5.0
    $325/hour
    Sailing Adventures on the Choptank River
    Sailing in Cambridge · 6 guests

    Sailing Adventures on the Choptank River

    New
    $100/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
    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
    VIKO S 35 Sailboat in Deale
    Sailing in Deale · 6 guests

    VIKO S 35 Sailboat in Deale

    New
    $298/hour
    Charter 44' Orana Cruising Catamaran In Deale, Maryland
    Sailing in Deale · 10 guests

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    5.0
    $250+/hour
    COME CRUISE THE BEAUTIFUL CHESAPEAKE BAY!
    Powerboats in Deale · 6 guests

    COME CRUISE THE BEAUTIFUL CHESAPEAKE BAY!

    5.0
    $200/hour
    Luxurious 51’ SeaRay Flybridge Yacht With Twin 600 Hp Cummins Engine
    Events in Deale · 10 guests

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

    5.0
    $500/hour
    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
    VIKO 30 Premium Sailing Yacht In Deale, MD
    Sailing in Deale · 5 guests

    VIKO 30 Premium Sailing Yacht In Deale, MD

    New
    $925/day
    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
    $350/hour
    43ft Cruiser Express Yacht for Daily Charter
    Events in Selby-on-the-Bay · 8 guests

    43ft Cruiser Express Yacht for Daily Charter

    5.0
    $400/hour
    31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD
    Powerboats in Selby-on-the-Bay · 10 guests

    31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

    5.0
    $275/hour
    Private Yacht Charter: On 40ft Regal Commodore
    Events in Selby-on-the-Bay · 10 guests

    Private Yacht Charter: On 40ft Regal Commodore

    5.0
    $350/hour
    Instant Book
    Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.
    Sailing in Mayo · 6 guests

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

    5.0
    $175+/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
    SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN
    Sailing in Annapolis · 12 guests

    SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

    5.0
    $400+/hour
    SLOWDOWN - DUFOUR 430
    Sailing in Annapolis · 12 guests

    SLOWDOWN - DUFOUR 430

    New
    $250+/hour
    JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!
    Sailing in Annapolis · 12 guests

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

    5.0
    $250+/hour
    STARZ -Lagoon 42 Catamaran in Chesapeake Bay
    Sailing in Annapolis · 13 guests

    STARZ -Lagoon 42 Catamaran in Chesapeake Bay

    5.0
    Snoozed - Active 02 Oct 2025
    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
    50ft Catamaran Charter with Water Toys - Annapolis, MD
    Sailing in Annapolis · 12 guests

    50ft Catamaran Charter with Water Toys - Annapolis, MD

    5.0
    $325/hour

    Top Destinations Nearby

    Oxford Reviews

    1. JH

      Jessica

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

      This was such a great trip! The boat is Beautiful and Michael & Norma were wonderful! We felt right at home. If you are looking for a boat trip, I would 110 recommend Michael! It was such a great experience. We will be returning.

    2. JV

      Javier

      Private Yacht Charter: On 40ft Regal Commodore

      Captain Dennis was an amazing host. We came with a group of 10 and everyone had an amazing experience. The boat is amazing and Captain Dennis will make sure you have a great time!

    3. EW

      Edward

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

      Sarah did an excellent job to arrange our trip and respond to our questions.

    4. CB

      Caroline

      Private Yacht Charter: On 40ft Regal Commodore

      Captain Dennis is absolutely fantastic. Great communication, fabulous boat and amenities, and a wonderful captain. Would highly recommend!

    5. MR

      Matt

      STARZ -Lagoon 42 Catamaran in Chesapeake Bay

      Great experience and our family and friends had a wonderful time. Clean boat and fun crew to help us celebrate a special occasion. Highly recommend!

    6. hg

      hunter

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

      we did our engagement pictures on the boat & everything was great! Bill was super cooperative & made sure we got all of the best spots for pictures! highly recommend!

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