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    Browse Chesapeake Bay Boat Rentals.

    Average of 1,532 reviews in this area.
    1 - 18 of 180 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

    41' Lagoon Cruising Catamaran in Maryland, United States
    hour$349
    Super Owner12 guests

    41' Lagoon Cruising Catamaran in Maryland, United States

    $150 HR | 8 people |
    hour$150
    Super Owner8 guests

    $150 HR | 8 people |

    💎🛥1️⃣of a Kind Luxury Cruisers Sports Yacht‼️🍹☀️
    hour$500
    Super Owner6 guests

    💎🛥1️⃣of a Kind Luxury Cruisers Sports Yacht‼️🍹☀️

    $275 HR | 8 people + Water Activities
    hour$275
    Super Owner8 guests

    $275 HR | 8 people + Water Activities

    $400hr Weekdays | $450hr Weekends | Luxury Yacht
    hour$400
    Super Owner14 guests

    $400hr Weekdays | $450hr Weekends | Luxury Yacht

    Yacht | $250 HR | 8 people
    hour$250
    Super Owner8 guests

    Yacht | $250 HR | 8 people

    Cruiser Boat | 8 people | $200 HR
    hour$200
    Super Owner8 guests

    Cruiser Boat | 8 people | $200 HR

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

    "3 BuOYS" Regal 38 SAV

    2021 Brabus Shadow 500 Cabin Luxury Adventure in Virginia Beach!
    hour$237
    Super Owner12 guests

    2021 Brabus Shadow 500 Cabin Luxury Adventure in Virginia Beach!

    "Imi Ola" Seawind 1260
    hour$716
    Super Owner12 guests

    "Imi Ola" Seawind 1260

    Top Luxury 2021 Brabus Shadow 500 Cabin Adventure Boat in Hampton, Virginia!
    hour$237
    Super Owner12 guests

    Top Luxury 2021 Brabus Shadow 500 Cabin Adventure Boat in Hampton, Virginia!

    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
    hour$125
    Super Owner6 guests

    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    100+ results

    GetMyBoat customer reviews for boat rentals in Chesapeake Bay.

    1. De’Ara
      De’Ara
      Enjoy the scenic routes of Washington DC on the Upper Potomac on this luxurious yacht with Captain Rod Patterson

      An amazing experience. Captain Rod and his crew were professional, communicative, and great to work with. The vessel was polished and had a high-quality sound system for my music lovers. Highly-responsive and quick service too. Would definitely book again.

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

      We signed up for a three hour tour with Captain Alberto and had an outstanding experience. From timeliness and preparation to his extensive knowledge of sailing the and Annapolis sailing community, he provided a great morning. We were able to help as much or as little as we wanted and able to simply enjoy a wonderful morning on the water. Many thanks for a wonderful time, hope to catch up with you again soon! Jason

    3. MH
      Meredith
      41' Lagoon Cruising Catamaran in Maryland, United States

      Jess was the best captain we could have asked for!! He was communicative and on schedule as planned. He ensured all of our safety while we were aboard his boat. The boat was clean and spacious; everything we could have wanted!! We chartered the boat as a fun addition to our bachelorette weekend celebrations and we all couldn’t stop talking about how fun it was!!! We are already talking about planning another trip back for another boat day with Jess! I highly recommend you book with him for your next celebration or for simply a fun and relaxing boat day with friends/family! I would give Jess and our experience 10 stars out of 5 if I could! Thanks so much again, Jess!

    4. GREGG
      GREGG
      $400hr Weekdays | $450hr Weekends | Luxury Yacht

      This is an amazing boat and GREAT staff. They made us feel so at home on the boat and provided drinks for the entire party! Great sunset cruise seeing the monuments. Large boat and great Captains! We will definitely use them again.

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

      Captain Alberto was super knowledgeable and a gracious host. He helped explain the basics of sail to my friends who had little knowledge of the activity. He offered itinerary suggestions and was super accomodating. We would sail with him again.

    6. ss
      sadaf
      $275 HR | 8 people + Water Activities

      Our trip with Dilmar was amazing! He was soft spoken, laid back and helped us with our coolers/bags we brought with us. Abadi and Dilmar were in contact from the time the booking was confirmed up until our trip. We were a group of 8 girls (one wasn’t able to make it last minute) and there was plenty of room for everyone to sit and move around throughout the boat. Pricing was fair and the included water activities was a plus! We were able to play our own music via Bluetooth and use some of the space in the fridge to keep some food items cool. I would recommend get my boat to friends and family and would recommend this owner and captain as well! We will be booking again in the near future, preferably not on one of the hottest days of the summer :-)

    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 has 180 listings for boating experiences in Chesapeake Bay with 1,532 reviews.

    Search Chesapeake Bay