Top 5 Yacht Charters In Chesapeake Bay, USA - Updated 2024

Contributing Writer
| 3 min read

Chesapeake Bay is the largest estuary in the United States and harbours a variety of animal and plant species, as well as important urban centres, including Baltimore and Annapolis. The Chesapeake Bay Watershed spans six states and the District of Columbia, making it a strategically and economically important region. Pivotal historic moments of the USA, including some battles of the American Revolutionary War, were also played out here. Chesapeake Bay is home to several freshwater mussels, which are vital in sustaining and creating aquatic habitats in the region. If you’d like to learn more about the region’s ecological importance, visit the Chesapeake Bay Environmental Center in Grasonville. If you want a deeper insight into the splendour of Chesapeake Bay, it would be best if you explore it on a yacht. For great options, scroll down for the top yacht charters in Chesapeake Bay, USA.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on July 16, 2024.

1. Luxurious sailing yacht with a kitchenette, Annapolis (from USD 166)

This luxurious yacht is essentially a floating apartment with its collection of amenities, which includes a well-equipped galley kitchenette and a dining saloon. It also houses two separate cabins, one of which is furnished with a king-size bed while the other is equipped with a full-size bed. A crib and a travel cot are also available here, convenient for those travelling with children.

The rental even comes with laundry appliances, making it great for long-term stays. Note that private sailing cruises can only be arranged at an additional charge.

Stayed at this property?
Annapolis, Maryland, United States
359 reviews   Superhost Wifi Available
Boat 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
and we got great restaurant reviews from ryan including iron rooster and preserve
the boat itself is in great condition and had all the amenities that a small apartment would have
my studio was exceptionally clean upon arrival
beautiful clean and convenient
everything was convenient and clean
ryan’s studio was impeccably clean and very well kept overall
super clean comfortable and convenient though a little exotic
ryan is the perfect host
ryan was a wonderful host
ryan was an excellent host
ryan is a great host everything is explained in great detail
ryan is a great and attentive host
walking distance to many great places
great accommodations in an ideal location
the location is so convenient to many great restaurants and just a short walk to the downtown
great location right across the bridge from annapolis within walking distance of restaurants historic sites and stores
great location with easy walking access to eastport and annapolis
Read more reviews

2. Affordable yacht with an HDTV, Pasadena

If you’d prefer a simple and affordable yacht for your vacation, you should opt for this compact 30-foot-long (9-meter) ship. Its efficient use of space means that up to six guests can be accommodated onboard. It even has a tiny kitchenette equipped with a microwave, so you can prepare quick meals while out on the bay. The HDTV with Amazon Prime Video and Roku subscriptions ensures that you won’t be bored even if you have to stay indoors.

Stayed at this property?
Pasadena, Maryland, United States
Wifi Available
Boat 4 Beds 6 Guests 1 Bedroom 1 Bathroom

Accommodates: 6

3. Sleek yacht with chic decor, King George (from USD 225)

This elegant yacht is bound to be the ship of your dreams with its chic decor and elegant interiors. Note that yacht cruises are booked separately and start from a price of 1,250 USD for a four-hour tour. This price is applicable for up to eight guests. If you’re interested in only booking a cruise, you are requested to contact the host directly so that alternative arrangements can be made.

Cruises aren’t available in winter, however, you can still book the yacht if a leisurely stay is all that you are looking for. There’s a lounge on the deck where you can relax and relish the views of the bay.

Stayed at this property?
king george, Virginia, United States
20 reviews   Wifi Available
Boat 3 Beds 4 Guests 7 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the bed is extremely comfortable and the hot water is plentiful
the boat was a great experience and david was a great host
david was a great host that was very accommodating and quick to respond to any questions
david is definitely one of the kindest and patient individual i've every met
he was so kind welcoming and very flexible with me
could not have hoped for more hospitable accommodating and lovely hosts
the serenity was docked at the national harbor - a great location for both scenery and things to do
Read more reviews

4. Seafood, Stevensville

This 60-foot (18.3-meter) yacht is perfect for accommodating a large group looking forward to exploring the waters of Chesapeake Bay. However, note that a cruise on the bay will incur additional charges and have to be arranged in advance.

The yacht is equipped with WiFi, so you can stay connected even while cruising along the shore. Parking spaces are provided by the host, so you don’t have to worry if you’re driving here.

Stayed at this property?
Stevensville, Maryland, United States
54 reviews   Superhost Wifi Available
Boat 5 Beds 6 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 6

Top guest reviews
the owner was great to work with and provided the ultimate customer service
rich was a great host
rich is a gracious host
excellent hosts and an awesome experience
the host was very nice and he responded back to emails quick
a fun spot in a beautiful location with tons of very unique character
this is a great location and setting to relax and enjoy the water
just a super place to stay
Read more reviews

5. Pet-friendly yacht with a full kitchen, Baltimore (from USD 85)

If you’re looking forward to a yacht charter that allows you to easily explore the urban delights of Baltimore, you should opt for this 42-foot (12.8-meter) ship. It is situated near Fells Point, which is a trendy neighbourhood of the city, dotted with charming pubs and extravagant restaurants. The yacht is moored on a secure dock, so you can be assured of your safety here.

Note that the host can arrange harbour cruises for an additional charge. However, guests do not have access to the engine room and are barred from handling the controls. The yacht has a compact kitchen equipped with a stove, oven, microwave, and refrigerator, allowing guests to prepare meals onboard. If you want to take your pooch along with you on the bay, you’ll be delighted to know that this rental has a pet-friendly policy.

Stayed at this property?
Baltimore, Maryland, United States
680 reviews   Wifi Available
Boat 3 Beds 4 Guests 2 Bedrooms 1 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
very comfortable and quiet sleeping nice to sit on deck and watch the harbor
beds were really comfy though ac was great
great unique experience there is a full bed and two small ones plus a small couch so spacious boat
the ac units were a nice surprise and made the temperature comfortable even in the rain
toilets are a bit cramped and cranky but the marina has access to nice showers and toilets
bed was comfortable and very clean
the boat was clean and well appointed and the pier it is on is a quiet residential area
amazing location super clean and cozy
it’s not a fancy boat but it was comfortable and clean
this boat rocks very comfortable and clean
very nice boat and host
lots of friendly boat owners nearby
his directions and instructions were clear and helpful
great host very respectful and responsive
cristhian was a great host and was very quick to answer any questions that we had
such a cool space and great location
cool space in a great location
it’s a good neighborhood and pretty close to fells point
location was amazing and the experience was fun
christian was great and it was close to everything
Read more reviews

Have an enjoyable vacation aboard a yacht in Chesapeake Bay

Chesapeake Bay is a remarkable estuary that is best explored on a ship so that you can have the full experience. For an excellent vacation, book one of the above yachts in Chesapeake Bay, USA.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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