Annapolis, Maryland’s capital city, has incredible attractions for all types of travelers. The trolley tours, the museums, the wineries, and great outdoor opportunities provide an endless list of things to do and see. But how exciting would it be for you to retreat to a boat for the night once you are done with your day’s wandering? Well, having your accommodation in a waterfront Vrbo rental or on a boat is another great experience you should consider, given that Annapolis has many lovely vacation rentals with incredible sea views. Does going for boat accommodation on your next Annapolis trip sound like a good idea? Consider the following options if you would like to rent a boat 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 October 25, 2025.
1. Chanceuse (from USD 208)
Step into this charming waterborne treasure, where a picturesque river view and delightful marina scene await, offering ultimate tranquility by the waterfront. Inside, you’ll find three snug cabins and a fully equipped kitchen, creating a perfect retreat for up to six guests. Immerse yourself in the rich history as you explore the captivating areas of Annapolis, Eastport, St. John’s College, and the Naval Academy.
Stay comfortable with AC, reverse cycle heat, and reliable Wi-Fi for your convenience. And when winter arrives, we’ve got you covered with two thoughtful space heaters to keep you warm and toasty.
Annapolis, Maryland, United States
1.61 km (1.0 mi) from Annapolis City DockSuperhost
Accommodates: 6
Top guest reviews
Host:
maryline is an excellent host and her sailboat was absolutely perfectRead more reviewsCleanliness:
the boat was immaculately clean and very cozy and warm
2. Gorgeous studio boat in Annapolis Harbor (from USD 442)
This is a former sailboat that is currently being used by the owner as a studio. It is small, clean, and elegantly furnished in white and soft shades of blue that creates an incredible atmosphere in the interior for sleeping and resting. This boat rental in Annapolis, Maryland is comfortably equipped with a galley kitchenette, two private cabins, a small bathroom, a small desk, and a dining saloon with comfy couches. One cabin has a king bed while the other one has a normal full bed. On the deck is a comfortable cockpit and a small folding table. If you are a couple in need of a quiet weekend getaway, then this boat will give you the magic you need for your accommodation.
Annapolis, Maryland, United States
616 meters (0.4 ft) from Annapolis City DockAccommodates: 4
Top guest reviews
Host:
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 hostLocation:
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 annapolisCleanliness:
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 exoticRead more reviewsAmenities & 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 have
3. Comfortable, well-equipped Hatteras yacht (from USD 785)
If you are looking for a luxury getaway in Annapolis, Maryland, then look no further! This is a beautiful yacht that exudes comfort both on the outside and the inside. The yacht features a white theme with elements of cream and brown in the interior, where you will also find lavish furnishings accentuated by soft color lighting. The yacht has two bedrooms fitted with three beds, hence, spacious enough for up to four guests. The aft cabin has a queen bed, while the forward cabin features two bunk beds. It has a fully equipped kitchen in the galley and a couch for resting in the salon.
Annapolis, Maryland, United States
985 meters (0.7 ft) from Annapolis City DockAccommodates: 4
4. Spacious and neat sailboat (from USD 192)
The sailboat has two sleeping cabins fitted with two beds, giving it the capacity to sleep up to six guests. The interior is immaculately designed, with a spacious seating area that features lots of soft lighting. The air-conditioned sailboat also comes every amenity you will need for a relaxed night of getting buoyed on the Annapolis docks, and these include an HD cable TV, high-speed WiFi, a microwave, a toilet, and a refrigerator among others. With close proximity to downtown Annapolis, attractions and amenities will be just a stone’s throw away from the boat.
Annapolis, Maryland, United States
1.8 km (1.2 mi) from Annapolis City DockAccommodates: 4
Top guest reviews
Host:
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 hostLocation:
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 outstandingCleanliness:
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 convenientRead more reviewsAmenities & 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 networks
5. Stunning sailboat with top-notch facilities (from USD 1078)
Welcome to this stunning sanctuary with its soaring ceilings and five chic staterooms, each boasting its own private bathroom and entertainment setup. You’ll bask in the beauty of natural light during the day and stargaze at night. The fully-equipped galley will have you feeling like a master chef, and the teak cockpit is perfect for enjoying your morning coffee or having a delightful al fresco dinner.
This Airbnb sailboat in Annapolis, Maryland is the ultimate gem with its high-tech goodies, including a sound system that can groove in every room, an array of gaming consoles, and even a Wii for endless fun. When you’re on land, indulge in the resort-like facilities of the marina with a dazzling pool and a top-notch fitness center. Plus, you’re just a stone’s throw away from exploring historic Annapolis, Washington DC, and Baltimore!
Annapolis, Maryland, United States
1.4 km (0.9 mi) from Annapolis City DockAccommodates: 12
Top guest reviews
Read more reviewsHost:
the hosts were very welcoming and helpful every step of the waywow it was wonderful on the boat what a great stay and owner thanks so so much
6. Huge luxury yacht (from USD 564)
Ths yacht rental is huge, beautiful, and luxurious, both on the inside and outside. With a total of three bedrooms and four beds, this 50-foot (15 meters) yacht can comfortably sleep up to 9 guests. All the bedrooms are equipped with 730-count linens. The boat has two main levels – the main deck with both rear and front decks, as well as a double trampoline ideal for sunbathing while you enjoy the views of the ocean and the harbor. For cooking and eating convenience, the boat has a fully equipped galley kitchen. The salon has a total of six seats where guests can lounge while they watch a movie or eat their meals.
Annapolis, Maryland, United States
614 meters (0.4 ft) from Annapolis City DockAccommodates: 9
Top guest reviews
Read more reviewsHost:
ren was a gracious host and the boat was incrediblehosts were nice and easy to communicate withthe catamaran was in fantastic condition for us and ren was a super hostren was an excellent host but wouldn't expect anything less from a fellow canadianhis friendly disposition and accommodating nature provided us an exceptional experience aboard his vessel
7. Gorgeous yacht with beautiful waterfront views (from USD 225)
This yacht is a 50-foot (15 meters) ocean yacht docked within a beautiful neighborhood in the Eastport region. It has three bedrooms fitted with four beds and hence has enough space to sleep up to five adults. Also featured are two full baths and a couch that is big enough to be used by an adult as a bed. The location of the yacht is within a walking distance to most of the attractions and entertainment spots around the port. The location also makes access to shopping and dining amenities in downtown Annapolis a breeze. With a complete kitchen, a well-furnished salon, and entertainment just close by, the boat has everything you may need for a unique living experience at the waterfront.
Annapolis, Maryland, United States
806 meters (0.6 ft) from Annapolis City DockAccommodates: 5
Top guest reviews
Host:
kate was a great host and thought of everythingRead more reviewsLocation:
what a unique and great place
8. Air-conditioned sailboat for eight (from USD 495)
If you are a group of up to eight fun-seekers in need of boat accommodation in Annapolis, then this will be more than a natural choice for you. The boat has air conditioning in all cabins to ensure you are very comfortable irrespective of the weather conditions outside. It is spacious on the inside, with all the necessary amenities you may need for comfortable stays, including a spacious seating area and a well-equipped kitchenette. Whether you are in need of an interesting venue for out-of-town family trips, bridal parties, staycations, or business meetings, the vessel is sufficient to provide you with all you need.
Annapolis, Maryland, United States
360 meters (0.3 ft) from Annapolis City Dock
9. Kathleen Marie
If the idea of motion on the water isn’t your thing but you still crave the charm of a yacht getaway, this rental is your perfect match. It offers a cozy forward cabin with bunk beds, an aft cabin with a queen bed, and a fully equipped galley for that home-like comfort. Spend your time relaxing in the living area with a Smart TV and Bose speaker or enjoying stunning views of Chesapeake Bay from the deck.
Not in the mood to cook? Explore nearby restaurants. You can also take a short trip to shop and visit famous landmarks. This 43-foot (13.11-meter) Hatteras yacht is just 5 minutes from downtown Annapolis by car, so you get the best of both worlds—city attractions and waterside relaxation.
Annapolis, Maryland, United States
1.07 km (0.7 mi) from Annapolis City Dock
Top guest reviews
Host:
lena and her husband were perfect hosts—communicative gracious attentive (but not too much so)mena was very helpful and responsiveLocation:
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 viewsRead more reviewsCleanliness:
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 view
Spend a night in a boat in Annapolis
It is not every time you will get the opportunity to spend the night on a boat while you enjoy the gentle tossing of the waves on the harbor. Vacation rentals and hotels are very common, and if you are in a place like Annapolis and can rent a boat for accommodation, you should always seize the opportunity. Use the above list to find unique accommodations in Annapolis, Maryland for a thrilling stay on the waters.
Frequently asked questions about renting a boat in Annapolis, Maryland
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