Awesome boat rentals in Chesapeake Bay, United States.
1 - 18 of 138 listings
Charter 29ft Crownline Bowrider In Wildwood, NJ / Cape May, NJ
Charter a Boat for Exciting Tour and Watersports in Virginia Beach, Virginia!
Dream it. Live it! Rent and Ride this 45' Sea Ray Sundancer Yacht in Washington, DC
Enjoy the scenic routes of Washington DC on the Upper Potomac on this luxurious yacht with Captain Rod Patterson
Explore Chesapeake Bay by water with an amazing boat rental.
Chesapeake Bay is an amazing place to rent a boat. From a motor boat to a sailboat to a yacht, you're sure to find the perfect boat rental. Take in the beautiful scenery and spend quality time with your friends and family while having the perfect day on the water. Whether you're planning a family vacation, a romantic getaway or a trip with friends, Chesapeake Bay is a great boat rental destination.
Using GetMyBoat to rent your next boat.
Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.
Search for the perfect experience now and book your dream day out on the water.
GetMyBoat customer reviews for boat rentals in Chesapeake Bay.
- CQ
Corine
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
Captain Alberto and his wife were so welcoming and fun to sail with. They let us be a little involved with the sailing and steering, which we loved, and were super flexible with the itinerary. The boat was very well taken care of and we loved going across the Chesapeake. We cannot wait to book with Captain Alberto again, but this time with our parents!
- BS
Bilal
BEST DAY EVER! $325/hr WEEKENDS $275 WEEKDAYS
John was a great host! He was responsive, reliable and personal. I planned on doing a surprise proposal during the ride and he helped me plan the whole thing! He took us to an area with a nice backdrop of Lincoln Memorial for the special moment and was very helpful throughout the whole process. I am extremely satisfied with the experience and would highly recommend John!
- AJ
Amanda
Hit all the DC Waterfront destinations on this beautiful 29ft Motor Yacht! Very accessible pricing! Book your next Private Charter today!
Captain Shane was extremely communicative and professional handling my transaction. The vessel was able to accommodate the Father’s Day event I planned. The gentlemen aboard raved about the quality of the catered meal that was an added amenity. I would highly suggest adding a meal to your charter. I was able to add small touches to make the evening ride special and unique (balloons, water cooler, fruit tray, etc). I was most impressed by the cleanliness and quality of the vessel. He sent pictures of the vessel (interior and exterior) to assist in my planning. Any questions I had he answered and provided a wealth of information ahead of the event. The booking was thorough from start to finish. I had another booking that fell thru at the last minute and S and S Charters was ready to accommodate me during the same week. I’m happy I found S and S! Thank you for creating an experience that will last a lifetime. I will book again and recommend others to think about S and S Charters as their first option!
- AM
Angela
Charter 29ft Crownline Bowrider In Wildwood, NJ / Cape May, NJ
This was an amazing trip and cannot wait to do it again. We are local but not boaters and did this for my birthday. An excellent, comfortable boat...with a captain very interested in our comfort. We enjoyed every second. Commodore Steve is very knowledgeable about the area, extremely welcoming, and is pretty excellent at honoring any request. Don't hesitate to book,
- SK
Sunny
2016 Regal 31' CruiseThe Inner Harbor, Annapolis, Hart Miller Island, Jelly Fish Joel's Tiki
What a memorable evening !! Thank you Shawn for the hospitality . It was an absolute fun with the whole family .. thank you for making us feel like home and specially with two infants onboard .. we would certainly recommend and look forward to more evenings .. Cheers !!
- HH
Hayley
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
Alberto and his wife Grace were the most wonderful hosts!! We spent 4 hours cruising around downtown Annapolis and had SO much fun!! Alberto and Grace were kind, flexible, and wonderfully hospitable. They made our girls weekend absolutely perfect and we can’t thank you enough for such a wonderful boat ride! If you have the chance to book with Alberto, we couldn’t recommend him more!! We will definitely be coming back!!