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    Browse Chesapeake Bay Boat Rentals.

    Average of 1,385 reviews in this area.
    1 - 18 of 188 listings
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
    hour$150
    Super Owner6 guests

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

    ⭐️ 5-Star Luxury Motor Yacht in Washington, District of Columbia
    hour$350
    Super Owner6 guests

    ⭐️ 5-Star Luxury 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

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

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

    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

    SeaRay $250/hr - 9 people
    hour$250
    Super Owner9 guests

    SeaRay $250/hr - 9 people

    Yacht $275/hour - 9 people
    hour$275
    Super Owner9 guests

    Yacht $275/hour - 9 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!

    $400hr Weekdays / $450hr Weekends Private Luxury Yachting
    hour$400
    Super Owner12 guests

    $400hr Weekdays / $450hr Weekends Private Luxury Yachting

    "Arabella" Meridian 341
    hour$671
    Super Owner6 guests

    "Arabella" Meridian 341

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

    "Allon-Z" Jeanneau MC11

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

    "Stress Free" Four Winns Vista 348

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

    "3 BuOYS" Regal 38 SAV

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

    "Imi Ola" Seawind 1260

    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. LH
      Lindsay
      22' Bennington Pontoon..Best prices in DC $150 weekdays/ $185 weekends + Jet Skis Available for addt'l costs...

      Bobby was a super dad by taking our crew out today to celebrate Father’s Day!! Even though some parts of the Potomac were choppy due to the wind, Bobby knew where to go to keep it calm for our families with 4 little ones on board. Super grateful for this once in a lifetime experience! The view of the monuments were spectacular!!

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

      Alberto and his wife Grace were such amazing hosts! My family enjoyed the 3hr boat trip despite the windy day. Capt Alberto definitely has amazing skills when it comes to steering and managing the boat, especially when the weather can cause some trouble on the water. We all felt so safe with both Alberto and Grace because they knew what they were doing! They were such great company, we highly recommend taking a trip with them and we will definitely plan to book with them again soon!

    3. LS
      Lisa
      ☀️🛥🔺No Extra Fees🔺$250hr Weekdays / $350hr Weekends Premium Private Yachting🍹🏝

      Best way to spend my birthday... Captain Shane made us feel comfortable from the moment we boarded the yacht....he was so cool...he felt like family...exceeded my expectations!!! Worth every penny. Cant wait to book again!!

    4. Kim
      Kim
      ⭐️ 5-Star Luxury Motor Yacht in Washington, District of Columbia

      We sent a last minute request for the same day within 2 hours of the desired booking time and were surprised with the prompt response and accommodations made for us. We loved every minute of the charter on the beautiful yacht and can’t wait to return. We rode up the Potomac to the 3 sister islands in between Georgetown and Great Falls and just couldn’t have been happier with the relaxing scenery.

    5. AW
      Asia
      ☀️🛥🔺No Extra Fees🔺$250hr Weekdays / $350hr Weekends Premium Private Yachting🍹🏝

      If you’re contemplating booking, do it now!! We had the most amazing time. Captain Shane was a pleasure and made sure we enjoyed every moment of our ride. We felt like VIP. We are apart of the SS family now and will be booking again!

    6. ng
      noelia
      SeaRay $250/hr - 9 people

      This was my first time using this service and they did not disappoint. I rented this boat for my birthday and had such an amazing time with my group of friends! The captain Dilmar was such a vibe he was super friendly and a great host! Will be booking again and highly recommend to anyone looking for a good time on the water, thanks again :)

    GetMyBoat has 188 listings for boating experiences in Chesapeake Bay with 1,385 reviews.

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