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Browse Chesapeake Bay Boat Rentals.

Page 7 of 9208 listings

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!