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    Browse Chesapeake Bay Boat Rentals.

    5.0
    (1,677 Reviews)
    • Recommended
    • Price: Low to High
    • Price: High to low
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    Most Popular Yachts in Chesapeake Bay

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    • Paint, party and yacht with us! Climb aboard the 45ft Sea Ray
      Events in Washington · 12 guests

      Paint, party and yacht with us! Climb aboard the 45ft Sea Ray

      4.7
      $345+/hour
      Instant Book
    • $275hr | 8 ppl | Grill and BBQ Family & Friends Boat
      Powerboats in Washington · 8 guests

      $275hr | 8 ppl | Grill and BBQ Family & Friends Boat

      5.0
      Superowner
      Best of 2025
      $275/hour
    • Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.
      Events in Washington · 6 guests

      Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.

      5.0
      $220+/hour
    • Spacious Luxury Carver 37' in Washington D.C.
      Events in Washington · 13 guests

      Spacious Luxury Carver 37' in Washington D.C.

      4.7
      $199+/hour
    • $350hr|10 people| Luxury Yacht
      Events in Washington · 10 guests

      $350hr|10 people| Luxury Yacht

      5.0
      Superowner
      Best of 2025
      $350/hour
    • $275 HR | 8 people | Sea Ray 330 Sundancer Yacht
      Events in Washington · 8 guests

      $275 HR | 8 people | Sea Ray 330 Sundancer Yacht

      5.0
      Superowner
      Best of 2025
      $275/hour
    • Bayliner Small boat | 6 ppl | $150hr
      Events in Washington · 6 guests

      Bayliner Small boat | 6 ppl | $150hr

      5.0
      Superowner
      Best of 2025
      $175/hour
    • Chaparral 350 Signature Motor Yacht Rental in Washington, District of Columbia
      Events in Washington · 9 guests

      Chaparral 350 Signature Motor Yacht Rental in Washington, District of Columbia

      5.0
      $300/hour

    Boats to Book Now

    The quickest way to get out onto the water.

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    • 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

      5.0
      $200/hour
      Instant Book
    • 2022 Sea Ray SDX Boat with Captain Included!
      Powerboats in Edgewater · 6 guests

      2022 Sea Ray SDX Boat with Captain Included!

      New
      $250/hour
      Instant Book
    • Fishing Charter in Pasadena, Maryland
      Fishing in Riviera Beach · 6 guests

      Fishing Charter in Pasadena, Maryland

      5.0
      $840/day
      Instant Book
    • Ride on our 50 Passenger Navigator Boat!
      Events in Washington · 50 guests

      Ride on our 50 Passenger Navigator Boat!

      5.0
      $1,250/hour
      Instant Book
    • 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
      Instant Book
    • SEARAY SLX400 | $700hr | 13 People
      Events in Washington · 13 guests

      SEARAY SLX400 | $700hr | 13 People

      5.0
      Superowner
      Best of 2025
      $700/hour
      Instant Book
    • Charter 44' Orana Cruising Catamaran In Deale, Maryland
      Sailing in Deale · 10 guests

      Charter 44' Orana Cruising Catamaran In Deale, Maryland

      5.0
      $450/hour
      Instant Book
    • Party Cruises & Fishing Trips in Virginia Beach
      Fishing in Norfolk · 6 guests

      Party Cruises & Fishing Trips in Virginia Beach

      5.0
      $170+/hour
      Instant Book
    • Bugatti JetBoat - $300Hr - DC
      Powerboats in Washington · 4 guests

      Bugatti JetBoat - $300Hr - DC

      5.0
      Superowner
      Best of 2025
      $300/hour
      Instant Book
    • Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
      Sailing in Gloucester Point · 6 guests

      Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

      5.0
      Superowner
      $125/hour
      Instant Book
    • Great Center Console for rent in Ocean City
      Powerboats in Ocean City · 6 guests

      Great Center Console for rent in Ocean City

      4.8
      $150/hour
      Instant Book
    • Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis
      Powerboats in Annapolis · 6 guests

      Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis

      4.8
      $95+/hour
      Instant Book

    All Chesapeake Bay Listings

    Page 1 of 9 • 193 listings

    Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise
    Sailing in Oxon Hill · 6 guests

    Sailing Catamaran, National Harbor Ready for Sunrise, Sunset or Any Time Cruise

    5.0
    $240/hour
    50' Come enjoy the DC view on the Potomac river aboard Sancha
    Events in Washington · 12 guests

    50' Come enjoy the DC view on the Potomac river aboard Sancha

    5.0
    $375+/hour
    2023 12ft Highfield Tender
    Powerboats in Annapolis · 4 guests

    2023 12ft Highfield Tender

    5.0
    $63+/hour
    Paint, party and yacht with us! Climb aboard the 45ft Sea Ray
    Events in Washington · 12 guests

    Paint, party and yacht with us! Climb aboard the 45ft Sea Ray

    4.7
    $345+/hour
    Instant Book
    $400/hr Weekday & $750/hr Weekend
    Events in Washington · 20 guests

    $400/hr Weekday & $750/hr Weekend

    4.7
    Superowner
    Best of 2025
    $750/hour
    50’ Sea Ray Luxury Yacht on the Potomac. Experience luxury!
    Events in Washington · 12 guests

    50’ Sea Ray Luxury Yacht on the Potomac. Experience luxury!

    4.6
    Best of 2025
    $450+/hour
    Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.
    Events in Washington · 6 guests

    Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.

    5.0
    $220+/hour
    Luxurious Godfrey SweetWater Tritoon
    Powerboats in Fort Washington · 10 guests

    Luxurious Godfrey SweetWater Tritoon

    5.0
    $175/hour
    $250hr M-Th | $350 F-Su | 13 ppl | Luxury Boat
    Powerboats in Washington · 13 guests

    $250hr M-Th | $350 F-Su | 13 ppl | Luxury Boat

    5.0
    Superowner
    Best of 2025
    $350/hour
    Experience the Serenity of Sailing SV Magic
    Sailing in Mayo · 6 guests

    Experience the Serenity of Sailing SV Magic

    4.9
    $165/hour
    $200hr M-Th | $350hr F-Su | 12 ppl | Luxury Yacht SLX 350
    Events in Washington · 12 guests

    $200hr M-Th | $350hr F-Su | 12 ppl | Luxury Yacht SLX 350

    5.0
    Superowner
    Best of 2025
    $350/hour
    Instant Book
    2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island
    Powerboats in Annapolis · 8 guests

    2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

    4.9
    Best of 2025
    $225/hour
    Party on Catamaran |15 People | $300hr
    Powerboats in Washington · 15 guests

    Party on Catamaran |15 People | $300hr

    5.0
    Superowner
    Best of 2025
    $400/hour
    2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland
    Powerboats in Severna Park · 4 guests

    2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

    5.0
    $120/hour
    Starting at $50 HR | 16ft Center Console | York River | Fishing license included
    Powerboats in Gloucester Point · 4 guests

    Starting at $50 HR | 16ft Center Console | York River | Fishing license included

    5.0
    $50+/hour
    Instant Book
    Private Yacht Charter: On 40ft Regal Commodore
    Events in Selby-on-the-Bay · 10 guests

    Private Yacht Charter: On 40ft Regal Commodore

    5.0
    $300/hour
    Tubing & Wakeboarding | 8 ppl | all equipment included
    Water Sports in Washington · 8 guests

    Tubing & Wakeboarding | 8 ppl | all equipment included

    New
    Superowner
    Best of 2025
    $300/hour
    38-ft Hunter 376 Sailing Adventure in Annapolis
    Sailing in Annapolis · 6 guests

    38-ft Hunter 376 Sailing Adventure in Annapolis

    5.0
    Superowner
    $138+/hour
    Instant Book
    Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️
    Events in Washington · 12 guests

    Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️

    5.0
    Superowner
    Best of 2025
    $650+/hour
    Party Boat Rental Virginia Beach Charter 8 Seat Pontoon Boat Oceanfront FREE GAS
    Powerboats in Virginia Beach · 8 guests

    Party Boat Rental Virginia Beach Charter 8 Seat Pontoon Boat Oceanfront FREE GAS

    5.0
    $68+/hour
    JetCar Bugatti in Washington DC for Luxury Experience!!
    Powerboats in Washington · 5 guests

    JetCar Bugatti in Washington DC for Luxury Experience!!

    4.6
    $300/hour
    Charter 31ft Crownline Bowrider In Wildwood, NJ / Cape May, NJ
    Powerboats in Wildwood · 6 guests

    Charter 31ft Crownline Bowrider In Wildwood, NJ / Cape May, NJ

    5.0
    $250/hour
    Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
    Events in Annapolis · 8 guests

    Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

    5.0
    $250/hour
    $250hr Brand new SLX 310
    Powerboats in Washington · 6 guests

    $250hr Brand new SLX 310

    5.0
    Superowner
    Best of 2025
    $250/hour

    Chesapeake Bay Reviews

    1. Oneshia

      Oneshia

      Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.

      Our sail with Captain Troy was phenomenal! He was an absolute gentleman—attentive, fun, and made us feel completely at ease. The boat was spotless, and we felt safe and well cared for the entire time. We had an incredible experience and are already looking forward to sailing with him again!

    2. Luqman

      Luqman

      Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.

      Captain Troy made our boat trip unforgettable! He was professional, knowledgeable, and ensured we were comfortable and safe the whole time. With great stories and a fun attitude, he made the experience relaxed and enjoyable. Highly recommend booking with Captain Troy for a fantastic day on the water!

    3. J

      Jorge Alcazar

      2023 12ft Highfield Tender

      Alan made the extra effort to ensure the boat was ready on arrival and made return very simple. The boat fit exactly we will always recommend reach out to the best. He has proven support over and over !

    4. HH

      Hadiya

      Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.

      We had the most amazing time celebrating my birthday with Captain Troy. He is accommodating, kind, and very responsive, making the entire planning process seamless and stress-free. Captain created the best environment for us to be able to have fun and enjoy our charter. Will absolutely recommend and will book again!

    5. ST

      Sherzod

      38-ft Hunter 376 Sailing Adventure in Annapolis

      Great experience, it was my first time boat sailing and Alberto and his wife were great. My fiance and I had a great time. Highly recommend!

    6. Alvin

      Alvin

      50' Come enjoy the DC view on the Potomac river aboard Sancha

      Everything was amazing service fun and great energy

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