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    Browse Chesapeake Bay Boat Rentals.

    Average of 1,518 reviews in this area.
    1 - 18 of 185 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

    Yacht | $275 HR | 8 people
    hour$275
    Super Owner8 guests

    Yacht | $275 HR | 8 people

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

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

    Cruiser Boat | 8 people | $275 HR
    hour$275
    Super Owner8 guests

    Cruiser Boat | 8 people | $275 HR

    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!

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

    "3 BuOYS" Regal 38 SAV

    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

    Tubing | Wakeboarding | Cruising $150hr - 7 PPL
    hour$150
    Super Owner7 guests

    Tubing | Wakeboarding | Cruising $150hr - 7 PPL

    100+ results

    GetMyBoat customer reviews for boat rentals in Chesapeake Bay.

    1. 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!

    2. 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.

    3. 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 :-)

    4. LA
      Lauren
      ⭐️ 5-Star Luxury Motor Yacht in Washington, District of Columbia 🔸No Additional Fees 🔸

      We had a positive experience with the entire booking process. Communication and booking was seamless and we had the best time floating the Potomac! The captain was accommodating, helpful and fun. We had a great time and look forward to rebooking in the near future.

    5. DF
      Diane
      BEST DAY EVER! CLEAN BOAT! VERY EXPERIENCED CAPTAIN! $325/hr WEEKENDS $275 WEEKDAYS

      Ww had a beautiful sunset cruise to celebrate our anniversary. Thank you John! He provided everything we needed for a great night, including an amazing boat with upscale features & amenities. Did not disappoint! We highly recommend for a special DC boating experience.

    6. Stephanie and Mark
      Stephanie and Mark
      38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

      Captain Alberto was absolutely wonderful managing our family of 6, kids ranging 6-14, 2 of whom had never been on a sailboat of any kind before. (Note for newbies: bring a large bag of pretzels to help with seasickness. Grateful for the stash Captain Alberto had to share with us!) He was excellent at making everyone mindful of safety while allowing freedom to move around and enjoy his beautiful boat. Everyone got a chance to help/work in some way. The 6 year old cranked the winches! Our 12 year old (who was initially not enthused about sailing) manned the wheel for a LONG time with his encouragement & guidance. Less than a week later, that kid signed up for sailing camp back home in Colorado. :) Being native Baltimorean parents missing the Chesapeake, our day out with Captain Alberto was everything we had hoped for & more. Highly recommend.

    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 185 listings for boating experiences in Chesapeake Bay with 1,518 reviews.

    Search Chesapeake Bay