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    Chesapeake Bay, US Boat Rentals & Yacht Charters

    5.0
    (1,881 Reviews)

    Page 1 of 9 • 207 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    $350/hr Fri-Sun | $200/hr M-Th | 12 PPL
    Events in Washington · 12 guests

    $350/hr Fri-Sun | $200/hr M-Th | 12 PPL

    5.0
    Superowner
    $350/hour
    Instant Book
    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
    Superowner
    Best of 2026
    $270+/hour
    $400/hr Weekday & $750/hr Weekend
    Events in Washington · 18 guests

    $400/hr Weekday & $750/hr Weekend

    4.8
    Superowner
    $750/hour
    Unforgettable Boat Day | 11 ppl | $300hr
    Events in North Beach · 11 guests

    Unforgettable Boat Day | 11 ppl | $300hr

    5.0
    Superowner
    $300/hour
    $650 hr | 14 ppl | Luxury Yacht
    Events in Washington · 14 guests

    $650 hr | 14 ppl | Luxury Yacht

    5.0
    Superowner
    $650/hour
    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
    $225/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
    $100+/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
    39ft Regal Powerboat for Charter | 13 Guests | Annapolis
    Events in Arnold · 13 guests

    39ft Regal Powerboat for Charter | 13 Guests | Annapolis

    New
    Superowner
    $550/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
    $250hr Brand new SLX 310
    Powerboats in Washington · 6 guests

    $250hr Brand new SLX 310

    5.0
    Superowner
    $250/hour
    The Commodore Yacht | 13PPL | $500hr
    Events in Washington · 13 guests

    The Commodore Yacht | 13PPL | $500hr

    5.0
    Superowner
    $500/hour
    Party on a Catamaran |15 ppl| starting at $400hr
    Powerboats in Washington · 15 guests

    Party on a Catamaran |15 ppl| starting at $400hr

    5.0
    Superowner
    $450/hour
    SEARAY SLX400 | $550hr | 13 People
    Events in Washington · 13 guests

    SEARAY SLX400 | $550hr | 13 People

    5.0
    Superowner
    $550/hour
    Instant Book
    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
    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
    $300/hour
    Sea Ray Sundancer 285 Yacht | Self Driving Boat | 8 ppl
    Events in Washington · 8 guests

    Sea Ray Sundancer 285 Yacht | Self Driving Boat | 8 ppl

    5.0
    Superowner
    $300/hour
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
    Sailing in Rock Hall · 6 guests

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    5.0
    $150/hour
    Limited Availability
    53' Luxury Yacht for Charter in Washington, District of Columbia
    Events in Washington · 12 guests

    53' Luxury Yacht for Charter in Washington, District of Columbia

    5.0
    Superowner
    $400/hour
    Instant Book
    The Play Station-23 Foot Pontoon With Lights, Bluetooth, Charging Ports, Cooler
    Events in Fort Washington · 10 guests

    The Play Station-23 Foot Pontoon With Lights, Bluetooth, Charging Ports, Cooler

    4.9
    Superowner
    Best of 2026
    $225/hour
    Limited Availability
    Enjoy our World Class Service aboard Sea Ray 400 Sundancer
    Events in Washington · 10 guests

    Enjoy our World Class Service aboard Sea Ray 400 Sundancer

    4.9
    Superowner
    $400/hour
    Rent and Ride this 45' Sea Ray Sundancer Yacht in Washington, D.C.
    Events in Washington · 12 guests

    Rent and Ride this 45' Sea Ray Sundancer Yacht in Washington, D.C.

    5.0
    $333+/hour
    Cruise in Comfort Aboard "Chill Time" – 31ft Cabin Cruiser in Solomons Island
    Powerboats in Solomons · 6 guests

    Cruise in Comfort Aboard "Chill Time" – 31ft Cabin Cruiser in Solomons Island

    5.0
    $200/hour
    Luxurious Godfrey SweetWater Tritoon
    Events in Fort Washington · 10 guests

    Luxurious Godfrey SweetWater Tritoon

    4.9
    $195/hour

    Top Destinations Nearby

    Chesapeake Bay Reviews

    1. AH

      Alexandra

      38-ft Hunter 376 Sailing Adventure in Annapolis

      Alberto and Grace were the perfect team. They are kind, knowledgeable, respectful, communicative, safe and I would recommend them to anyone. This was our first time sailing in Annapolis, and we could not have asked for a better experience. We hope to share future experiences with them. Everything was perfect.

    2. WB

      Walter

      Luxurious Godfrey SweetWater Tritoon

      Our experience on the water with Phoenix was amazing! he is a very skillful captain who navigates the water with ease. We we're very impressed with his knowledge of the water and the nature around us. Phoenix has a warm energy about him that makes you feel like he is family. Will most definitely book again!

    3. BF

      Bruce

      38-ft Hunter 376 Sailing Adventure in Annapolis

      This was our 2nd sail with Capt Alberto. He is super friendly and easy to talk with. And he invites his guests to take an active role in sailing, or to just kick back and relax if they prefer. Great experiences for our family.

    4. MS

      Mars

      The Play Station-23 Foot Pontoon With Lights, Bluetooth, Charging Ports, Cooler

      I booked Troy for my Birthday Trip and we had an amazing time. Troy is an amazing person and boat captain and we had a lot of fun!!!

    5. CR

      Carmen

      The Play Station-23 Foot Pontoon With Lights, Bluetooth, Charging Ports, Cooler

      The group had a wonderful time on your boat. Very accommodating. Everyone had positive feedback. 10/10 recommend. Thank you!

    6. KG

      Kyle

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

      Troy was a wonderful host and we had a great time sailing.

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