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    Browse Chesapeake Bay Boat Rentals.

    Average of 1252 reviews in this area.
    1 - 18 of 134 listings
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
    hour$150
    Super Owner6 guests

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

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

    Charter a Motor Yacht in Washington, District of Columbia

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

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    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

    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

    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!

    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

    "Innamorata" 56' Salon Cruiser Chris Craft
    hour$805
    Super Owner6 guests

    "Innamorata" 56' Salon Cruiser Chris Craft

    "Soulmate" 47' Silverton 453
    hour$550
    Super Owner12 guests

    "Soulmate" 47' Silverton 453

    "Nautiday" 42' SeaRay 450 Sundancer
    hour$522
    Super Owner6 guests

    "Nautiday" 42' SeaRay 450 Sundancer

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

    "ADDIS" Wellcraft 260 SE

    BEST DAY EVER! $325/hr WEEKENDS $275 WEEKDAYS
    hour$325
    6 guests

    BEST DAY EVER! $325/hr WEEKENDS $275 WEEKDAYS

    22' Bennington Pontoon (jet skis avail addt'l cost)
    hour$165
    6 guests

    22' Bennington Pontoon (jet skis avail addt'l cost)

    41' Lagoon Cruising Catamaran in Maryland, United States
    day$1,849
    12 guests

    41' Lagoon Cruising Catamaran in Maryland, United States

    100+ results

    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. 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!

    2. DV
      Daniel
      Dream it. Live it! Rent and Ride this 45' Sea Ray Sundancer Yacht in Washington, DC

      Although I was primarily booking this boat for a group and did not partake in the actual festivities, I was very pleased with RJ , the captain, 1st mate and of course the boat. This was my 1st time renting a boat and RJ did a great job explaining protocol to ensure for a great time!

    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. KS
      Keertana
      Dream it. Live it! Rent and Ride this 45' Sea Ray Sundancer Yacht in Washington, DC

      Thanks RJ for the awesome boat trip!! Our group of 12 had a blast on this boat and RJ & his co-captain Joe were extremely friendly and accommodating. Prices were extremely reasonable & totally worth it for this experience. The boat was spacious and is a perfect idea for social gatherings. Would absolutely recommend and would love to book another trip soon!

    5. BN
      Brittany
      BEST DAY EVER! $325/hr WEEKENDS $275 WEEKDAYS

      We had a wonderful experience on Captain John Kemper‘s boat. My husband and I spent our third wedding anniversary on his boat touring the Potomac River of DC. John has a lovely boat with all the needed amenities. He was very personable and accommodating. We were able to have a romantic dinner on the water while taking in the lovely scenic views.

    6. AA
      Asheley
      BEST DAY EVER! $325/hr WEEKENDS $275 WEEKDAYS

      John was an amazing captain and made our time much more enjoyable. We did a photoshoot and John did everything he could to help make the photoshoot perfect. The boat was very clean and perfect for our needs. I can’t wait to book again!