15 Best Airbnbs in Annapolis, MD (2022 Edition)


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Annapolis, known as the sailing capital of the United States, is a small picturesque city outside of Baltimore on the shores of Chesapeake Bay. It is the ideal destination for a relaxing weekend getaway for couples and families. Tourists can spend their days lounging at the beach or strolling the streets of the historic downtown district and indulging in fresh seafood and boutique shopping. 

Whether you are visiting Annapolis for business or pleasure, you want to be guaranteed that you will be arriving at fantastic accommodation. We want that for you, too. That is why we here at Road Affair have created a list of the best Airbnbs in Annapolis, so you can spend less time researching and more time packing. All of the listings below are hosted by Airbnb superhosts, and some even boast Airbnb Plus status. For those unfamiliar with Airbnb, superhosts are rental owners with a track record of outstanding hospitality, while Airbnb Plus is an exclusive program that recognizes quality homes that have been in-person verified.

Related: 15 Best Airbnbs in Maryland

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Stylish Downtown Loft

This chic downtown Airbnb Plus is the ideal vacation rental in Annapolis for those looking to have all the attractions of downtown on their doorstep. 

The apartment has been decorated in a modern industrial style and features exposed brick walls and an abundance of natural light. In the bedroom, there is a comfortable queen-size bed where guests can relax after a day of touring the town. 

Downstairs has an open-concept layout with a full kitchen that includes a gorgeous wooden dining table and a Keurig coffee maker. Beside the kitchen, there is a small laundry area with a washer and dryer. Guests can choose a book from the extensive library in the living room and unwind on the pullout couch. 

This Annapolis Airbnb is within walking distance of many trendy cafés, waterfront restaurants, and lively bars. For those looking to catch a game at the Navy-Marine Corps Memorial Stadium, it is less than a five-minute drive away. Paid off-site parking is available at this rental. 

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Artsy Apartment in Eastport

Can you picture yourself cozied up in front of the fireplace in this stunning art-filled vacation home for rent in Annapolis? We definitely can. 

This flat boasts a sleek black-and-white color palette and features beautiful works of art created by superhost Tom. The entire space feels like you are staying in a modern gallery. The bedroom has a queen-size bed and luggage racks to make unpacking easier. In the bathroom, there is a gorgeous walk-in shower and complimentary bathroom essentials. 

Guests can relax on the large pullout sectional couch in the living room and stream their favorite shows on the Smart TV. A small kitchenette with a minifridge, coffee maker, microwave, and sink can also be found in the living area. 

This Airbnb is located in the neighborhood of Eastport, less than a five-minute drive from downtown Annapolis. Vin 909 Winecafe, as well as other restaurants and bars, is only a few steps from this rental. Free on-site parking and street parking is also provided for guests.

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Spacious House in Downtown 

If you are looking for a rental house in Annapolis that can sleep larger groups, this two-bedroom Airbnb downtown is for you. 

This newly renovated nautical-themed house is ideal for families or groups of six or fewer. The living room is bright and airy and features a pullout couch and a flatscreen TV. In the full kitchen, guests will find all the essentials for preparing a meal. There is also a small foldout red table in the kitchen that can be extended for more seating options. Guests can also opt to enjoy their morning coffee on the red rocking chair on the front porch or at the bistro set in the backyard. 

On the second floor, there is a bedroom that features a wooden desk and is decorated with nautical décor and patterned vintage furniture. The second bedroom is on the third floor and features beautiful light blue sliding barn doors, an exposed brick wall, and an en suite bathroom. Both bedrooms have a queen-size bed. 

This rental comes with access to free street parking and is only steps away from the United States Naval Academy. 

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Historic Row House 

This beautiful historic Airbnb in downtown Annapolis is ideal for families or those traveling on business. 

The house’s interior is fitted with polished wooden floors and repurposed wooden furnishings, creating a stylish and homey space. Guests can relax in the living room on the pullout couch and settle in with a book or watch TV. Beside the living area, there is a small dedicated workspace with a desk and chair where those looking to get some work done can set up their laptop. The full kitchen features stainless-steel appliances, a dishwasher, and a coffee maker.

The first bedroom features a barn door headboard and a queen-size bed. In the second bedroom, there is a large wardrobe for storage, a TV, and a queen-size bed. 

The backyard features a raised deck with patio furniture where guests can enjoy the sunshine with an afternoon cocktail, and the fenced-in green space is perfect for kids to kick around a soccer ball.

This charming Annapolis Airbnb Plus is located downtown, just steps away from popular restaurants, shops, and cafés. Free street parking is also provided.

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The Carriage House

If you are looking to rent a house in Annapolis that can sleep up to eight guests, then superhost Kristin has the Airbnb Plus for you. 

This bright and spacious home features high ceilings and statement furniture, creating a modern and comfortable space. In the master bedroom, there is a king-size bed with a memory foam mattress and plenty of storage space in the large wardrobe. The second bedroom features a queen-size bed with a memory foam mattress and a sofa bed. The bathroom features a beautiful double vanity and a spacious walk-in shower.   

In the full kitchen, guests can enjoy their meals at either the breakfast bar or the wooden dining table. The living room has a queen-size pullout couch and a TV with standard cable. 

Kristin has done a fantastic job making her rental family-friendly by stocking it with everything parents will need, like a baby monitor, toys, a baby bath, and safety gates. 

This home is located in West Annapolis, only a short drive away from downtown’s restaurants, bars, and museums. 

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Cozy Apartment With Free Parking

This cozy Airbnb in Annapolis is located just around the corner from the Annapolis Town Center and is ideal for solo travelers or couples. 

The home can accommodate four guests using the king-size bed in the bedroom and two queen-size blowup beds. Inside, the apartment has been furnished with comfortable and modern fittings, creating a relaxing space for guests to unwind in after a day of touring the city. 

In the full kitchen, guests will find everything they will need to prepare a meal and plenty of counter space to do so. The bathroom features a walk-in shower and a blow dryer in case a guest forgets one. There is a comfortable leather sectional couch in the living room where guests can unwind with a book or catch up on some TV. 

This Annapolis Airbnb is located in a quiet residential area just west of downtown. The Navy-Marine Corps stadium is about a five-minute drive away. 

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Main Street Apartment

If you are looking for a downtown Annapolis Airbnb, look no further than superhosts Matt’s apartment located right on Main Street. 

The home can sleep up to six guests and is right in the heart of downtown with its bars and restaurants. The Maryland State House, the United States Naval Academy, and St. John’s College are all within walking distance of the apartment. 

Matt goes above and beyond to make his guests feel at home by providing guests with complimentary wine and coffee. The living room features a leather pullout couch where guests can unwind with a cocktail after a day of touring the town. There is a small kitchenette that is well stocked with all the essentials, including a microwave, Keurig coffee maker, and a minifridge.

In one of the bedrooms, there is a queen-size bed, a TV, and a luggage rack. The second bedroom also features a comfortable queen-size bed. In the bathroom, guests can rinse off in the gorgeous walk-in shower. 

The home does not come with free on-site parking. However, paid off-site parking can be arranged. 

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Eastport Studio Apartment

This stylish studio guesthouse is one of the best Annapolis Airbnbs for solo travelers or couples who will be working from the rental. 

The home is set in the quiet neighborhood of Eastport on a well-spaced property surrounded by nature. Outside, guests will have access to a beautiful garden area complete with a patio dining set, a barbecue, and lounge chairs. 

The interior has been styled in warm reds and modern furnishings, creating a very welcoming space. The studio features a plush queen-size bed where guests can lie back and stream a movie on the Smart TV. Beside the bed is a desk and chair where those looking to get some work done can set up their laptop. There is a small kitchenette in the studio that features a minifridge, a coffee maker, and a sink. After a day of shopping, guests can pour themselves a glass of wine and unwind on the lounge chairs in front of the window. The bathroom has been designed as a European wet room and features a walk-in shower.

This Airbnb in Annapolis is within walking distance of the beach and seaside restaurants. Free parking is included. 

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Pet-Friendly House in Eastport

This stylish house for rent in Annapolis is a fantastic rental for small groups or families looking to bring their furry friends on holiday with them. 

This two-bedroom home has many great features, including a complimentary bottle of wine upon arrival. There is a spacious backyard where guests can play catch with their dog or grill a meal on the barbecue. 

The interior has been decorated with contemporary furniture that is both stylish and comfortable. In the living room, there is a large blue sectional couch where guests can relax and watch TV with a cup of tea. The full kitchen features a breakfast bar and plenty of counter space for cooking. In the master bedroom, there is a king-size bed, and in the second bedroom, there is a queen-size bed. The rental also has a washer and dryer, making this the ideal house for those looking to book a long stay. 

This Annapolis Airbnb comes with free parking on the premises. The home is in a quiet residential area of Eastport yet still within walking distance to some restaurants and bars. 

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The Ocean Apartment Downtown

From the moment you step in the door of this house rental in Annapolis, you will feel like you are floating in an ocean of blues. 

The apartment has been newly renovated and is designed in an array of different color blues and hardwood floors. In the living room, guests can access their favorite streaming services on the Smart TV. The full kitchen features a breakfast bar, a Moroccan mosaic tile splash, and custom cabinets. Guests can enjoy their meals at the small breakfast nook in the kitchen. The master bedroom has a comfortable king-size bed and a large walk-in closet. In the second bedroom, the mattresses can be set up to be two twin beds or one king-size bed. 

Note that superhost Megan does not allow children under the age of 12 years old to stay in this rental. Dogs are allowed for an additional fee. Parking is also included. 

This short-term rental in Annapolis is located near the Navy-Marine Corps Stadium, just a short walk away from the hustle and bustle of Main Street.

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Stunning Downtown Studio  

This Annapolis Airbnb Plus is the ideal rental for couples and solo travelers looking to be close to downtown. 

The home has been furnished in contemporary modern fittings and painted in light pastel green, giving a fresh feel to the space. There is a full kitchen complete with a coffee maker and a microwave. There is even a dishwasher, so guests can spend less time cleaning up and more time planning their next adventurous outing.

In the living area, there is a couch and a lounge chair where guests can settle in to watch TV or simply read a book. The bedroom area features a queen-size bed. The bathroom is gorgeous and includes a spacious walk-in shower. 

The home is located just southwest of downtown. Bars and local restaurants are only a short walk away, and the Navy-Marine Corps is just under a mile away. The United States Naval Academy is also less than a 10-minute drive away. Free street parking is provided for guests. 

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An Artist Retreat Near Naval Academy

Take one look inside this stylish and colorful studio apartment, and you will quickly see why it hits our list as one of the best Airbnb rentals in Annapolis. 

Playful pops of color, exposed wood beams, and contemporary furniture make this Airbnb Plus feel joyful and open. In the kitchen, there is a medium-sized kitchenette that includes a full-size fridge and ice maker, a sink, a breakfast bar, and a microwave. Guests won’t have to worry about staying warm after a shower as the bathroom comes equipped with heated floors and a walk-in shower. A washer and dryer can also be found in the bathroom. 

In the bedroom area, there is a plush queen-size bed with a pillow-top mattress, a Smart TV, and room-darkening shades. Superhost Linda has also provided a travel crib for those bringing their little ones along on holiday.

This studio is located in the quiet residential neighborhood of West Annapolis, near the United States Naval Academy. In the backyard of Linda’s home, guests have access to free on-site parking and a shared pool. 

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Downtown House for Larger Groups 

This charming three-bedroom home is located in the heart of downtown Annapolis and is ideal for those traveling in groups of six or fewer. 

This Airbnb has been professionally decorated with stylish décor and ocean blues, creating a relaxing space for guests. The full kitchen is well equipped with everything needed to prepare a meal and includes a Keurig coffee maker. There is a lovely dining area with a shimmering chandelier and a table to seat six guests beside the kitchen. The living room features a massive sectional couch where everyone can join together to watch a movie on the TV. 

Upstairs, there is a full bathroom with a gorgeous claw-foot bathtub where guests can enjoy a relaxing soak after a day of touring the town. The master bedroom features a unique sliding barn door, a queen-size bed, and a set of doors that lead to the back deck. In the second bedroom, there is a king-size bed, and in the third bedroom, there are two twin beds. Guests can spend an afternoon in the backyard grilling on the brand-new barbecue or lounging on the patio furniture. 

This Airbnb in Annapolis comes with one free parking space on the premises. 

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Historic Two-Bedroom House

If you are looking for an all-around American home with the white picket fence and all, this Annapolis Airbnb Plus is for you. 

This two-bedroom historic home has been exceptionally designed with chic furnishings, exposed brick, and a woodburning fireplace to create a welcoming and stylish space for guests. The kitchen has plenty of counter space for cooking and features a breakfast bar, a toaster, and a coffee maker. Alternatively, guests can head to the backyard and use the grill for cooking a meal. In the living room, guests can curl up on the comfortable cloth couch or in the leather lounge chairs and enjoy a cup of tea beside the roaring wood fire. 

Upstairs, bedroom one features a plush queen-size bed and a private balcony with a small bistro set. In the second bedroom, there is a queen-size bed and a wardrobe with plenty of storage space. 

This rental includes free parking on the premises and is located within walking distance of the Maryland State House and many popular restaurants and bars. 

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Charming Townhouse in the Heart of Downtown

This three-bedroom Annapolis Airbnb Plus is centrally located and perfect for groups of eight or fewer. 

The home was originally constructed in 1878 but has been renovated to reflect a more modern lifestyle while still keeping some of its historic details. In the living room, there is a sofa bed, a Smart TV with access to streaming services, and a DVD player. The full kitchen is well stocked with everything guests need to prepare a meal, including a double oven. There is also a barbecue in the backyard where guests can grill on those beautiful summer days. 

Upstairs, one of the bathrooms has a walk-in shower while the other features a vintage claw-foot soaking tub. In the master bedroom, there is a comfortable queen-size bed and a large walk-in closet with tons of storage space. The second bedroom features a daybed that converts into a king-size bed, and the third bedroom has a queen-size bed with a pillow-top mattress. 

Superhost Cristin has done an outstanding job stocking the home with family-friendly amenities such as children’s toys, outlet covers, a baby safety gate, and more. This Airbnb in Annapolis also comes with access to free on-site parking. 

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There you have it, the best Airbnbs in Annapolis! We hope that at least one, if not a few of these fabulous rentals, has caught your attention. Now all you have to do is pick one.

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