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    Browse Chesapeake Bay Boat Rentals.

    5.0
    (1,969 Reviews)

    Page 7 of 9 • 208 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Fun in The Sun Pontoon Rental w/Captain
    Powerboats in Washington · 10 guests

    Fun in The Sun Pontoon Rental w/Captain

    New
    $267+/hour
    $150 hr | 6 ppl | Center Console Boat
    Powerboats in Washington · 6 guests

    $150 hr | 6 ppl | Center Console Boat

    New
    Superowner
    Best of 2025
    $150/hour
    Instant Book
    44' Ocean Yacht Sportfisher in Ocean City, MD
    Fishing in Ocean City · 6 guests

    44' Ocean Yacht Sportfisher in Ocean City, MD

    5.0
    $250/hour
    Luxury Italian Vibe | 10 PPL | $600 HR
    Events in Washington · 10 guests

    Luxury Italian Vibe | 10 PPL | $600 HR

    New
    Superowner
    Best of 2025
    $600/hour
    Instant Book
    Not Your Average Pontoon: Seadoo Switch Cruise 21'
    Powerboats in Arlington · 8 guests

    Not Your Average Pontoon: Seadoo Switch Cruise 21'

    New
    $100+/hour
    Azimut Yacht | 13 People | $1100hr
    Events in Arlington · 13 guests

    Azimut Yacht | 13 People | $1100hr

    New
    Superowner
    Best of 2025
    $1,100/hour
    Instant Book
    Proline 23ft Center Console Fishing Boat for Charter in Suffolk
    Fishing in Hampton · 6 guests

    Proline 23ft Center Console Fishing Boat for Charter in Suffolk

    5.0
    $250/hour
    Adventure for 8 Monterey 322 Cruiser with Water Activities $300/hr
    Events in Washington · 8 guests

    Adventure for 8 Monterey 322 Cruiser with Water Activities $300/hr

    New
    $300/hour
    Cruise DC and turn heads aboard the vintage 1985 Chris Craft, American Pie
    Powerboats in Washington · 6 guests

    Cruise DC and turn heads aboard the vintage 1985 Chris Craft, American Pie

    New
    $300/hour
    Fish On! Rent Your 38ft Dawson Sportfish in Norfolk, VA
    Sailing in Norfolk · 6 guests

    Fish On! Rent Your 38ft Dawson Sportfish in Norfolk, VA

    New
    $725/day
    Fisherman’s Dream: 38ft Dawson Sportfish in Norfolk, VA!
    Fishing in Norfolk · 6 guests

    Fisherman’s Dream: 38ft Dawson Sportfish in Norfolk, VA!

    New
    $170/hour
    Enjoy the best views of Annapolis, MD aboard the Island Princess
    Events in Annapolis · 128 guests

    Enjoy the best views of Annapolis, MD aboard the Island Princess

    New
    $480+/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
    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
    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
    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
    Gone Fishin’ Sport Fishing Charters - Cape May
    Fishing in Cape May · 6 guests

    Gone Fishin’ Sport Fishing Charters - Cape May

    5.0
    $113+/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
    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
    24ft Bayliner Cierra Express Cruiser in DC
    Powerboats in Arlington · 6 guests

    24ft Bayliner Cierra Express Cruiser in DC

    New
    $250/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
    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

    Chesapeake Bay Reviews

    1. BA

      Brittney

      Proline 23ft Center Console Fishing Boat for Charter in Suffolk

      My first time on a boat and it was absolutely amazing. He made sure we were comfortable. During the trip I began to get a little motion sick but he took care of me. Our trip couldn't have been better. Thank you so much making my birthday so fun and memorable.

    2. April

      April

      44' Ocean Yacht Sportfisher in Ocean City, MD

      We booked with Troy for a private sea burial. He and his wife, Debbie, were very respectful and accommodating. I would rebook with Troy for any trip. His experience was invaluable. Thank you, Troy and Debbie.

    3. RD

      Ren

      Proline 23ft Center Console Fishing Boat for Charter in Suffolk

      It was awesome. great day and Cap is a super good guy - nice boat and he knows where the fish are

    4. GM

      Gabe

      Gone Fishin’ Sport Fishing Charters - Cape May

      We were early, and they were ready. On fish all trip. The 10 ur

    5. 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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