Annapolis boasts itself as a museum without walls and “America’s Sailing Capital.” As Maryland’s capital, it brims with an upbeat, modern vibe that blends well with centuries-old architectural works. It is renowned for its rich, nautical heritage, with its connection to Chesapeake Bay so you can expect to find various accommodations near the water, from luxury hotels to Vrbo waterfront vacation rentals. Famously, it is home to US Naval Academy (USNA), which has been providing education and training to US Navy officers since 1845. USNA has a museum commemorating the achievements and traditions of the US Navy and Marines. A trip to this historic city is not complete without touring Maryland State House, which once served as the capital of the fledgling United States. To have a genuine, local experience here, try sailing and rent a boat or yacht. Check out some of the best yacht charters in Annapolis, Maryland.
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 February 08, 2024.
1. Two-cabin yacht with a fully equipped galley (from USD 299)
This 13.11-m (43-ft) Annapolis boat rental is docked in Eastport, only a short walk away from the historic Downtown Annapolis and USNA. It features two private cabins, one with a queen-sized bed and another with bunk beds. Hosting up to four people, it has a fully functional galley where you can conveniently prepare home-cooked meals.
This galley is furnished with a coffee machine, a fridge, an ice maker, a microwave, a toaster, and a two-burner cooktop. In the main salon, you will find a couch that can serve as an additional sleeping space.
1.11 km (0.7 mi) from Annapolis City DockAccommodates: 4
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Cleanliness:
it was very clean and we had a wonderful viewthe accommodations are clean and very unique place to stay compared to the land alternativesboat was amazing—spacious clean as a whistle beautiful viewHost:
lena and her husband were perfect hosts—communicative gracious attentive (but not too much so)mena was very helpful and responsiveRead more reviewsLocation:
a great experience on the water and walking distance from annapolisan easy walk to many places to eat and explorebeautiful views walking distance to great food and unique atmosphereexcellent location with great views
2. Two-bedroom sailboat with a cozy cockpit (from USD 174)
This charter boat in Annapolis is essentially a two-bedroom apartment that will make you feel at home right by the sea, definitely, a great alternative to the equally amazing hotels on land. Accommodating a maximum of four guests, it has a full bathroom, a dining saloon with couches, and a fully stocked galley.
Since it is a family-friendly rental, you can request a folding bassinet in the forward cabin or a travel bassinet in the aft cabin for your little one. The boat also has a cozy cockpit up on the deck where you can unwind comfortably on a lazy afternoon. It is safely tied at the marina, so you have nothing to worry about during your stay.
Annapolis, Maryland, United States
616 meters (0.4 ft) from Annapolis City DockSuperhost
Accommodates: 4
Top guest reviews
Amenities & Room:
and we got great restaurant reviews from ryan including iron rooster and preservethe boat itself is in great condition and had all the amenities that a small apartment would haveCleanliness:
my studio was exceptionally clean upon arrivalbeautiful clean and convenienteverything was convenient and cleanryan’s studio was impeccably clean and very well kept overallsuper clean comfortable and convenient though a little exoticHost:
ryan is the perfect hostryan was a wonderful hostryan was an excellent hostryan is a great host everything is explained in great detailryan is a great and attentive hostRead more reviewsLocation:
walking distance to many great placesgreat accommodations in an ideal locationthe location is so convenient to many great restaurants and just a short walk to the downtowngreat location right across the bridge from annapolis within walking distance of restaurants historic sites and storesgreat location with easy walking access to eastport and annapolis
3. Luxury yacht with a double trampoline (from USD 475)
This 15.24-m (50-ft) luxury yacht rental in Annapolis is only a few minutes away from the downtown area. During winter, it is situated in the Bahamas. It features three bedrooms, which can host up to two adults each, and three full bathrooms. It can accommodate a maximum of 8 people, and it offers 83.61 sq. m (900 sq. ft) of living space. The salon can host two people with its king-sized dropdown table.
On the main deck, you will find a double trampoline that is perfect for sunbathing. Several chaise loungers are provided, so you will get to sit back, relax, and enjoy breathtaking views anywhere on the deck.
Annapolis, MD, US
More options for boat rentals in Annapolis
4. Two-cabin sailboat at a full-service marina
This 10.97-m (36-ft) Annapolis sailboat rental accommodates up to 4 guests and offers 2 cabins and a salon. It is docked at a full-service marina in Back Creek where you will find a bathhouse, a cafe, a supply store, a swimming pool, and a water taxi service. At the cafe, you can have your sumptuous breakfast and lunch meals.
The water taxis can take you to Downtown Annapolis and other nearby seafood restaurants and other waterfront dining options. If you are bringing a private vehicle, you can park for free in the marina’s parking area. The city center is only a 10-minute drive away.
Annapolis, Maryland, United States
1.8 km (1.2 mi) from Annapolis City DockAccommodates: 4
Top guest reviews
Amenities & Room:
amenities are nice including the bath house and poolthe boat is a comfortable stay with all the amenities you would needwe enjoyed sleeping on a boat we made the most of the pool in the marinaso we knew what to expect cool alternative to a hotel room in annapolisthe boat offers a small tv and dvd play for watching movies and regular cable networksCleanliness:
clean bathhouse is 100ft awaythe bath house is convenient and cleanbath house was very clean and closemarina was great bath house was clean and the pool was superthe marina facilities are clean and convenientHost:
ken is a great hostken was an excellent hostken was very responsive to questions and direction even though he was out of the countryeveryone was very friendlyken is a fantastic hostRead more reviewsLocation:
the location is perfect with close proximity to everythinglocation was great and very safethe location is quite private and safesafe place to stay and great locationi returned for another trip because the location in the marina atmosphere is outstanding
5. Cozy sailboat with access to the marina’s swimming pool
Only a few minutes away from Downtown Annapolis and roughly 45 minutes away from Washington DC, this cozy 9.14-m (30-ft) sailboat hosts up to 3 people. During your stay here, you will have access to all of its facilities, including the saloon and V berth. You will also have access to all other amenities that the marine provides, including the bathhouse, car park, and swimming pool. If you are bringing a private vehicle, you can take advantage of the marina’s complimentary parking. Wi-Fi is also available, so you can always stay online.
Annapolis, Maryland, United States
824 meters (0.6 ft) from Annapolis City DockAccommodates: 3
Find out why Annapolis is "America's Sailing Capital"
With its connection to Chesapeake Bay and USNA, Annapolis thrives on its rich, nautical heritage. Of course, you can always choose to stay in one of the hotels with tub or Airbnbs with pool on dry land but staying in one of these best yacht charters in Annapolis, Maryland, will likely make you realize how and why the city is known as “America’s Sailing Capital,” so go ahead and check them out.
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