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    Browse Chesapeake Bay Boat Rentals.

    Average of 1263 reviews in this area.
    1 - 18 of 141 listings
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
    hour$150
    Super Owner6 guests

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
    hour$150
    Super Owner6 guests

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    Charter a Motor Yacht in Washington, District of Columbia
    hour$350
    Super Owner6 guests

    Charter a Motor Yacht in Washington, District of Columbia

    Charter 29ft Crownline Bowrider In Wildwood, NJ / Cape May, NJ
    hour$250
    Super Owner8 guests

    Charter 29ft Crownline Bowrider In Wildwood, NJ / Cape May, NJ

    Jet ski - Jet Boat - 4 People - Sportster- SeaDoo - 16ft Be the Captain!
    hour$150
    Super Owner4 guests

    Jet ski - Jet Boat - 4 People - Sportster- SeaDoo - 16ft Be the Captain!

    Bayliner Yacht for $160/hour Weekdays - $200/hour Weekends - Up to 6 people
    hour$160
    Super Owner6 guests

    Bayliner Yacht for $160/hour Weekdays - $200/hour Weekends - Up to 6 people

    Sea Ray 300 Yacht Charter for $250/hr Weekend- $200/hr weekday- 8 people
    hour$250
    Super Owner8 guests

    Sea Ray 300 Yacht Charter for $250/hr Weekend- $200/hr weekday- 8 people

    J70 Daysailer rental in Hampton
    hour$100
    Super Owner4 guests

    J70 Daysailer rental in Hampton

    "3 BuOYS" Regal 38 SAV
    hour$575
    Super Owner10 guests

    "3 BuOYS" Regal 38 SAV

    "Stress Free" Four Winns Vista 348
    hour$599
    Super Owner8 guests

    "Stress Free" Four Winns Vista 348

    "Arabella" Meridian 341
    hour$671
    Super Owner6 guests

    "Arabella" Meridian 341

    "No Regrets" Regal Sport Coupe
    hour$562
    Super Owner6 guests

    "No Regrets" Regal Sport Coupe

    "S.S. CamJoy II" Chaparral Signature 270
    hour$570
    Super Owner6 guests

    "S.S. CamJoy II" Chaparral Signature 270

    "Allon-Z" Jeanneau MC11
    hour$398
    Super Owner8 guests

    "Allon-Z" Jeanneau MC11

    "ADDIS" Wellcraft 260 SE
    hour$278
    Super Owner6 guests

    "ADDIS" Wellcraft 260 SE

    100+ results

    Boating Guide - Chesapeake Bay

    Chesapeake Bay Boat Rentals

    One of the best experiences you can have on the east coast of the United States is a boat rental on the Chesapeake Bay. Book a sailboat charter for an all-encompassing tour of the bay and see the stunning shoreline from the water. Boat tours and fishing on the Chesapeake Bay are not only great for tourists but are also fabulous experiences for life-long locals to enjoy in the summer. There are many water tours and types of boating experiences you can have on the Chesapeake Bay. Choose from pontoon rentals, sailboat rentals, bareboat rentals, yacht charters and even houseboat rentals.

    GetMyBoat customer reviews for boat rentals in Chesapeake Bay.

    1. rc
      raymond
      38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

      I cannot speak highly enough about Capt. Alberto. He and his ‘first mate’ gave us a great morning on the bay. A chilly but sunny morning with good wind kept us thoroughly engaged in the sailing. The Capt and his wife were easy to spend time with. Their love and knowledge of sailing and their warmth made for good conversation and a relaxing day. The boat is comfortable and well maintained. Even with some stiff breezes we stayed dry. When my wife got chilly, they provided a blanket to keep her warm. Very thoughtful and appreciated. Capt. Alberto gave me the helm for a time and allowed me to sail a beautiful boat. It topped off a perfect day. Thanks Cap! We’ll be back.

    2. Melissa
      Melissa
      38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

      We had the best time with Captain Alberto! He was so nice and professional. His many years of experience is obvious and he shared so much of his knowledge with us. Our time together gave us such a huge appreciation and love of sailing! We can’t wait to go again!

    3. WD
      William
      Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

      Sailing with Captain Joe was like spending an afternoon sailing with your buddy Joe. Friendly, gracious, knowledgeable, and highly skilled Joe made for a relaxing and enjoyable sail. The Beneteau is a very comfortable and roomy boat and we would definitely book another sail with him!

    4. CK
      Christine
      Bayliner Yacht for $160/hour Weekdays - $200/hour Weekends - Up to 6 people

      This was a perfect, fun experience! We took our parents for their 40th wedding anniversary for a short private boat ride. They had so much fun, and we got to see the Lincoln Memorial and Georgetown waterfront. Sam was a great captain, and everything was great! I highly recommend and will definitely book again.

    5. DS
      Dan
      38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

      Capt Alberto and his wife Grace are amazing hosts and people! This was our families first trip on the Getty oat site and we’re happy to choose this one. The boat was in pristine condition and even though there wasn’t much wind the day we went out, the Capt searched and found some! The kids were able to steer and learn about sailing. All in all a perfect morning and would definitely recommend to anyone!

    6. nd
      nancy
      Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

      A beautiful day on the water! We were in great hands with Captain Joe- very hospitable, and a skilled sailor. Highly recommend!

    GetMyBoat has 141 listings for boating experiences in Chesapeake Bay with 1263 reviews.

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