14 Delightful Airbnb Annapolis Vacation Rentals

The treasure of the Chesapeake Bay, known for its brick-paved streets and historic Maryland  State House is also the home of the best Airbnb Annapolis. Take a tour of the U.S. Naval Academy or United States Sailboat Show and see for yourself why Annapolis is one of the top 10 places in America where people decide to go and spend the rest of their life.

Check out the best Airbnb Annapolis MD has to offer and visit the United States Sailboat Show or take a tour of the U.S. Naval Academy!
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Why Should You Book Airbnb in Annapolis Maryland?

If you are planning your trip to this charming city, we strongly suggest you first check out the list of top Airbnb in Annapolis that will make your stay complete. These lovely homes are the best places to stay in while visiting Annapolis and no matter which of these you choose, you will have a perfect Airbnb rental in Maryland all to yourself.

Take a look at the photos of these delightful Annapolis Airbnb homes, and decide how and where you want to spend your vacation. One thing is for sure – Annapolis and its best vacation rentals will make you feel relaxed and comfortable.



Beautiful and Tranquil Carriage House – About $199.00

Airbnb Annapolis Beautiful and Tranquil
Credit: Airbnb

A unique high-ceiling living area with white palette walls will leave any guest with a feeling of peace and tranquillity. This beautiful Airbnb in Annapolis is a perfect option if you want to take amazing pictures both outside and inside. Pass through the French door, and go out on the balcony to enjoy the amazing surroundings. With 2 bedrooms and 4 beds, up to 8 people can be accommodated in the coziness of this home.

8 guests | 2 bedrooms | 4 beds | 1.5 baths

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2003 Craftsman; Heart of Eastport! – About $200.00

Airbnb Annapolis 2003 Craftsman
Credit: Airbnb

Astounding Annapolis Airbnb home with over 2,000 square feet at your disposal. Unwind in any of 3 bedrooms, and make delicious meals in a gourmet kitchen. Perfect for families or large groups, this house can be entered through the back yard or front porch where you can meditate over a cup of morning coffee.

8 guests | 3 bedrooms | 4 beds | 2.5 baths

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Charming Rowhouse in Historic District – About $69.00

Airbnb Annapolis Charming Rowhouse
Credit: Airbnb

Enchanting Airbnb Rental in Annapolis with a themed interior that matches the town’s navy spirit. If you are visiting in late April and you are a sailboat enthusiast, then this is the right home for you. 2 bedrooms with 3 beds can easily fit 6 people. Take a stroll through the town during the day, and relax in the red rocking chair on the porch.

6 guests | 2 bedrooms | 2 beds | 1 bath

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Cozy Home near Historic Downtown –  About $199.00

Airbnb Annapolis Cozy Home
Credit: Airbnb

Located on West Street, just a short drive to the shopping area of Annapolis, this lovely home is just what every tourist needs. This extraordinary house has 4 astonishing bedrooms and 2,5 bathrooms, so you can bring both family and friends! With plenty of things to do in Annapolis, like take a tour of the U.S. Naval Academy, you will need a place like this to get a good rest and to recharge.

8 guests | 4 bedrooms | 5 beds | 2.5 baths

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Charming Renovated Historic Home Downtown – About $199.00

Airbnb Annapolis Charming Renovated
Credit: Airbnb

Only two blocks away from the city dock this Airbnb downtown Annapolis is everything you hoped for and more. Just picture specially designed paradise – a large English garden outside, and inside, a 3-bedroom and 2-bathroom interior. Contact the host if you wish to bring your dog along since well-behaved ones are more than welcome. Also, your host can be a superb travel guide, and direct you to everything you should see and do.

6 guests | 3 bedrooms | 5 beds | 2 baths

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Hideaway in the Middle of Everything – About $225.00

Airbnb Annapolis Hideaway
Credit: Airbnb

Stay at one of the most bustling streets that is Severn Ave. This Airbnb Eastport Annapolis is a splendid hideaway for families since, besides 2 queen beds, it also includes a kids’ loft bed, so your little ones have a space of their own. You would be situated next to Annapolis Yach Club and Spa Creek Bridge.

10 guests | 3 bedrooms | 6 beds | 2 baths

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3BR/2BT Entire House By Chesapeake Beach Club – About $129.00

Airbnb Annapolis Entire House By Chesapk
Credit: Airbnb

Picture a green oasis just 5 minutes away from Chesapeake Beach Club. This home is absolutely perfect for couples, families or even for those of you who are visiting this area on business. With 4 bedrooms and 2 completely renovated bathrooms, you will have enough space for you and your fellow travellers. If you wish to stay away from all the tumult of the main street, but still be in the area, this is the right home for you.

5 guests | 3 bedrooms | 4 beds | 2 baths

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Peaceful Waterfront Home & Pier 4mi. from downtown – About $220.00

Airbnb Annapolis Peaceful Waterfront Home
Credit: Airbnb

A movie-like waterfront house is a truly unforgettable experience. Combine a calm getaway with all the picturesque surroundings that will make your next vacation photos into a true sensation. A 10-minute drive to downtown, this Airbnb Annapolis MD home has 4 bedrooms, with 10 beds and 3 bathrooms. Feel free to take the kayaks and paddle through the cattails, or follow the shoreline of the Chesapeake Bay. Whatever you decide to do, you will shortly realize why this place is one of the best vacation rentals in Annapolis.

10 guests | 4 bedrooms | 10 beds | 3 baths

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Walden hop to Annapolis, DC, or Baltimore! – About $85.00

Airbnb Annapolis Walden hop to Annapolis
Credit: Airbnb

If you are looking for a private, comfortable apartment area, and you are travelling with a friend or two, we might have found your ideal place. Great for younger people, or families this Airbnb Annapolis basement studio can welcome 4 guests. Enjoy the serenity of a quiet neighbourhood and relax next to a fire pit lounge in the back yard.

4 guests | 1 bedroom | 2 beds | 1 bath

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Country House on the Bay – About $85.00

Airbnb Annapolis Country House on the Bay
Credit: Airbnb

A stunning view of the Chesapeake Bay with a cozy and comfortable interior is the best way to describe this spacious home. Even though the host’s accommodation is on the second floor, you will have a private space all to yourself as well as a separate entrance. An additional plus is that the master bedroom is handicapped accessible.

8 guests | 4 bedrooms | 7 beds | 3 baths

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6+ bed / 3 Full bath Annapolis Luxury and Style – About $349.00

Airbnb Annapolis Full bath Annapolis
Credit: Airbnb

If you like to travel in style this luxurious Airbnb rental in Annapolis will meet your standards. This gigantic house has 6 queen beds and can host up to 16 people, so it suffices to say that it is a match made in Heaven for people travelling in large groups. A completely equipped kitchen, 3 full bathrooms, and 2 living rooms will be more than enough reasons for you to pack light.

16+ guests | 5 bedrooms | 8 beds | 3 baths

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“Cattail” A Photographer’s Waterfront Retreat – About $125.00

Airbnb Annapolis Cattail
Credit: Airbnb

Special retreat from the hustle and bustle of the cities lies 30 minutes away from Annapolis. Equipped with 4 bedrooms, and a hot tub in the common area, this house is a marvellous getaway made for anyone. Spend your day outside fishing, walking or exploring the coastline. Or stay inside and cuddle up under the blanket with your loved ones in front of the TV. Regardless of what you choose to do, this Airbnb home will exceed your expectations.

9 guests | 4 bedrooms | 6 beds | 3.5 baths

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Pure BARCELONA 2 – About $150.00

Airbnb Annapolis Pure BARCELONA 2
Credit: Airbnb

Book this Annapolis Airbnb and stay just across the street from Navy-Marine Corps Stadium! Ideal for 4 friends or 2 couples. The guests will have access to the kitchen, living area, and 1,5 bathroom. If you are travelling by car, there are 4 off-street parking spaces at your disposal.

4 guests | 2 bedrooms | 2 beds | 1.5 baths

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Beautiful New Studio Efficiency – About $175.00

Airbnb Annapolis Beautiful New Studio
Credit: Airbnb

Entire private rental studio for you and your special someone! Or a friend! This Airbnb Eastport Annapolis studio is located within walking distance to downtown. A queen futon bed, private bath, and a kitchen that will make you feel cozy and at home. Use the back yard for a barbecue or for resting after a long day.

2 guests | 1 bedroom | 1 bed | 1 bath

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We hope you loved our this list of Airbnb properties and it helped you find a great place to stay. Have you stayed in any of the Airbnbs on our list? Or have you found other great Airbnbs in this city that you are keen to get featured? We are always on the lookout for great experiences and amazing places to stay. Join the conversation and let us know below.

Looking for great Airbnb vacation rentals in other cities? Check out some of our favourites below.

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Kris Ryan Quirino
Kris Ryan Quirino

I'm a travel writer, researcher and engineer with two wonderful little kids. When I'm not taking care of my kids. I'm travelling and writing for various blogs online. My passion is renewable energy and I am currently completing a Masters part time in solar systems.

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