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2 boat rentals in Chester, MD, USA

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Renting a boat is the perfect way to explore Chester, MD

Rent a yacht in Chester to see this stunning location like you’ve never seen before. With a private boat rental from Sailo, you and your family or friends will have the freedom to discover some of the most beautiful parts of Maryland. Whether you choose a sailboat, catamaran or a motorboat, you are in for a thrilling, romantic and unforgettable adventure aboard your private yacht charter.

Curious about your options for renting a party boat in Chester, MD?

Planning for a private event with your family or friends or a business occasion that you’d like to celebrate in a special way? Choose one of our top rated party boat rentals in Chester, MD! 2 event boats with capacity of 13+ guests are available in Chester, offering a variety of catering package options, entertainment and professional crews trained to make your special event unique and memorable. Rent a party yacht in Chester, MD from Sailo: it’s easy, quick, secured and the best way to surprise your guests with an exclusive experience on the water!

Learn how to find the perfect yacht for you

Sailo has the most advanced filters to help you find the perfect boat rental for an amazing experience on the water in Chester, MD. Start your search by choosing your start trip date, duration and number of guests. For a great day trip with your family or friends, you have the option to select 2, 4 hours or full day rentals. Depending on your preferences and budget, you may narrow your results by boat type and price range. The 'crew' filter allows you to check the boat rentals with the captain included in the price, skipper optional (paid as extra) or bareboats that you’ll captain yourself (boating resume required). Once you have laid your eyes on a boat you like in Maryland, click on it to read the description, reviews and see more pics. We also recommend using our direct 'Message Owner' feature that allows you to start a conversation with the boat representative to ask away everything you want to know before you submit a booking request.

How much is it to charter a Chester, MD yacht for a day?

Whether you are looking to rent a yacht for a city sightseeing tour, a romantic sunset cruise or an active day on the water with your family or friends, we're confident you’ll find the best one for you on Sailo. The average starting price to charter a yacht in Chester is $1100. You can however find excellent affordable rentals from $250 and also elegant yacht charters that can go up to $6500 (service fee and mandatory extras not included).

If I rent a yacht on Sailo, will I get insurance coverage?

Yes, all Sailo boats available for rental have insurance: sometimes included in the price, other times available to buy as mandatory extra.

Sustainable yachting tips

If you’re looking to explore our beautiful planet, a yacht charter is a great place to start. Explore coral reefs with your snorkel, discover hidden bays and islands and generally enjoy the view of nature. Remember, that sailing motto: 'Take only photos, leave only wake' (OK, so we paraphrased). To be a responsible sailor, remember:
  • Don’t disturb coral or sealife
  • Take your trash home (and don’t throw anything in the sea)
  • Respect the locals and their customs wherever you go
Read more about responsible boating.