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Apartment holiday rentals in Annapolis

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Annapolis

Guests agree: These apartments are highly rated for location, cleanliness and more.

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Guest favourite
A leather couch with decorative cushions is positioned in a well-lit living area. A modern piece of artwork adorns the wall behind the couch, while potted plants add a touch of greenery. Bright natural light filters through two glass-paneled doors.
Apartment in Annapolis
4.92 out of 5 average rating, 503 reviews

Wall to Wall Cool- Filled with Original Art and Sculpture

This apartment is on one end of a larger main house. The shared wall was retro-fit with sound dampening cellulose fill in February of 2018. This enhancement along with many others provide the feel and comfort of being in your own space. This is Listed as 2 bedrooms, however there is no door between the 2 rooms. They are separated by 3 steps and a hallway. Please see pictures for a thorough view of the layout. Proximity to destinations; Vin 909 0.2 miles, Boatyard Bar & Grill 0.3, Eastport bridge, gateway to the downtown area 0.7 miles, City Dock 1.1 miles, Naval Academy 1.2 miles There is a Murphy Queen cabinet Bed, plus a Leather couch that turns into a queen bed allowing 4 to sleep comfortably, 2 to a bed. Very calm and relaxed space, a great place to recharge as you discover the area. Of Note: Hotel cleanliness standards vary greatly; with comforters frequently being a little dubious. Just how many turnovers are factored in before they get washed? High traffic carpeted floors can hide unwanted history. Walking in your bare feet should only make you feel free, never uneasy. Our pledge; every guest will sleep on clean sheets, over a freshly sanitized mattress cover under a bed comforter or bed blanket that was cleaned before their visit. When shams are present, they are laundered every single time. All surfaces are cleaned and if something’s not right, let us know and it will be. Life can be a mystery, but your Airbnb stay should never be. Shared Use of the Front porch to the right of the house. Wifi, (2) 4K TV's one 48" and the other is 60", industrial under counter fridge that will keep everything nice and cold. Dishes, glasses plates are all available. The (2 ) Roku TV remotes have inputs for standard ear buds, so you can stay up way late and watch TV while not waking up your friend/spouse/relative, buddy, just plug in... I'm kind of a non-intrusive, sort of do my own thing sort of person. Very mindful not to step on other peoples good times. Available through text to answer any questions you may have. I've lived in the area most of my adult life and am always happy to help. The house is in the eclectically odd neighborhood of Eastport. It's close to great restaurants, bars, and pubs. Vin 909 Winecafe is less than a five-minute walk from the house, and it's across the street from three more restaurants and a drug store. Walk it man, walk it! it's good for you and what's the rush. Driving downtown can be painful and crowded. Plus why pay the man to park, when you've got free parking at the house? Proximity to destinations; Vin 909 0.2 miles, Boatyard Bar & Grill 0.3, Eastport bridge, gateway to the downtown area 0.7 miles, City Dock 1.1 miles, Naval Academy 1.2 miles The house is on a main road to downtown. So there is a fair amount of traffic in front of the house. There is also a fire station just down the road, so passing sirens often accompany the din of general city traffic. For your comfort there is a white noise machine in the front bedroom area. There is also a small fan in the closet if you prefer to sleep with a fan. Please use caution when pulling out of the drive way. When walking downtown, the side streets are much quieter, so pick the path that best suits you.

Top Guest favourite
The open-concept living space features a combination of comfortable furniture, including two green chairs and a gray sofa. A wooden coffee table occupies the center of the room, surrounded by an area rug. A fireplace and bookshelves add warmth and character to the setting.
Apartment in Sykesville
4.95 out of 5 average rating, 218 reviews

Hickory Haven •1B King •Bsmt Apt •Clean •LG

Walk into a generously spacious, open-concept apt. The comfortable furnishings in this home blend authentic styles with modern design. Start your mornings w/ a meticulously clean bathroom. Enjoy movie night in the large living room, or lay on the comfortable king-sized bed. Read through the night by a warm stove fire. Stay in the backyard and enjoy the serenity of Sykesville! Enjoy the high-speed internet and the large space for your work-at-home needs. Stay-a-while and make the place your home.

Superhost
A spacious bedroom features a large bed with striped bedding and decorative pillows. A colorful upholstered bench sits at the foot of the bed. Soft light is provided by two bedside lamps, and natural light filters in through the windows with white trim.
Apartment in Annapolis
4.88 out of 5 average rating, 299 reviews

Gybeset Eastport Inn

Enjoy exclusive use of this boutique hotel-styled upstairs apartment in a beautifully restored 1930s craftsman-style building in the heart of Eastport. Private off-street parking. Short walk to downtown Annapolis. Just a few doors away from one of the hottest restaurants in Annapolis, Vin 909. A seasonal farmers' market is located across the street along with restaurants and other amenities. Hotel-like services available for longer stays. Fully licensed by City of Annapolis for AirBnb operation.

Top Guest favourite
The studio apartment features exposed brick walls, enhancing its character. A spacious bed with a vibrant orange coverlet is positioned beside two bedside lamps. A large area rug adds color, while a television is visible across from the bed, complemented by an additional couch and decorative plants.
Apartment in Upper Fells Point
4.86 out of 5 average rating, 907 reviews

Stay in a Former Fells Point Bar! - Private Studio

Rent a unique studio apt in Fells Point! This is no cookie-cutter Airbnb. We converted a portion of our home, a 19th century construction & mid-20th century Fells Pt bar, into a 500 foot apartment w/private entrance, bathroom, work & living space. The apartment is near Fells bars & restaurants, Canton, Hopkins, the harbor, Patterson Park & downtown. 2 miles from stadiums. There is a 6 in. incline from sidewalk to entrance. Access ramp available. No steps in studio. We only host via Airbnb.

Top Guest favourite
A close-up view of the sleeping area features a full bed with an earthy-toned quilt and decorative pillows. A soft throw blanket rests at the foot of the bed. Above, a series of wooden wall art pieces adds a touch of warmth, while a 55-inch Smart TV is mounted nearby.
Apartment in Bowie
4.93 out of 5 average rating, 147 reviews

Just Like Home - Private Entrance Apt in DMV Area

288 SQ FT PRIVATE ENTRANCE Mother-in-law suite/ studio apt, full bed, sofa, roll-away single bed, kitchen, bathroom with small shower stall & 55” Smart TV w/cable, Netflix & WiFi. No guests under 12 years of age. Excellent location: Ft. Meade (14.4 miles), Annapolis (15 m), Andrews AFB (19 m), Washington DC (19 m), Baltimore (29 m) Nearby airports: DCA (23 m), BWI (27 m), IAD (48 m) Public Transportation: Metro Bus Stop (0.2 m), New Carrollton Station Metrorail, Amtrak, & Greyhound (9 m)

Superhost
A bright living space is highlighted by large windows with wooden shutters. A modern sofa faces a small coffee table and a bookshelf. A potted plant adds a touch of greenery, while eclectic furnishings and artwork provide a personal touch. Light streams in, creating an inviting atmosphere.
Apartment in Union Square
4.93 out of 5 average rating, 567 reviews

Urban 1-Bedrm. Apt. Overlooking Union Square Park

The south-facing, 2nd floor 1-bedroom apartment of an owner-occupied historic townhouse overlooks historic Union Square Park in Baltimore City. Located 2 doors from the author, H.L. Mencken's home place, the neighborhood is primarily residential , but very convenient to the Inner Harbor. The apartment has a full kitchen (with light breakfast items), historic details & eclectic furnishings. Street parking is easy. The space is good for couples and solo adventurers, and business travelers.

Guest favourite
The entrance features a welcoming front door adorned with a decorative wreath, flanked by windows with shutters. A small stairway leads up to the door, with a concrete path that is surrounded by greenery.
Apartment in Annapolis
4.92 out of 5 average rating, 112 reviews

King George Hideaway

Perfect location for all that downtown Annapolis offers, right across from USNA gate 2. Super convenient, park your car and walk everywhere! Lots of shopping, restaurants, tours, cruises & nightlife. The unit is located on the 3rd floor. My place is perfect for couples, solo and business travelers. There is a large living room space with a full pull out couch, tv and dining table. The bedroom has a queen bed with a tv. There is a small full kitchen and updated bathroom.

Guest favourite
The sleeping area features a spacious bed dressed in white linens, complemented by a decorative pillow. Two large windows, framed with sheer curtains, allow natural light to fill the room. A bedside table holds a lamp, and a closet is visible in the corner.
Apartment in Hyattsville
4.84 out of 5 average rating, 328 reviews

Small cabin style- 23 min drive to US Capitol!

This in-law suite is better defined as a small apt. attached to house; own entrance, bathroom, kitchen & free parking! Queen bed, clean sheets, towels, iron, board, kitchen pots, dining table, TV & more. It’s small but with all amenities necessary to live. If looking for a huge space, this will not be it. Good for single/couple cruising by the DMV on a BUDGET! -20 min walk to metro; off DC border, 18 min. drive to center of city.

Superhost
Aerial view of a marina surrounded by a cluster of homes and colorful trees, with numerous boats docked along the waterfront. The scenic landscape features water and docks, with the horizon showcasing more boats and buildings in the distance.
Apartment in Annapolis
4.77 out of 5 average rating, 287 reviews

Charming Eastport

Who needs a boat to stay at a marina? Eastport Yacht Center has a quaint one bedroom apartment located in charming Eastport, within walking distance to Downtown Annapolis and the U.S. Naval Academy. Conveniently located next to the Annapolis Maritime Museum. (Two guests maximum) If this apartment isn't available for your time period check out our other studio apartment listed under "NEW lovely studio apartment with onsite parking".

Guest favourite
The living area features a spacious sectional sofa in neutral tones, accompanied by a glass coffee table. A large mirror enhances the sense of space, while colorful decor items are visible on a nearby bookshelf. Light from recessed lighting creates a bright ambiance.
Apartment in Bloomingdale
4.92 out of 5 average rating, 438 reviews

Spacious & Modern Apt in Historic Neighborhood

Enjoy a retreat in a recntly renovated basement apartment in DC with free street parking and convenient access to all the hustle and bustle of downtown! Amenities include smart lock/alarm allowing for self check-in/out; spacious bedroom with a Duxiana queen bed; living room with comfy couch and smart TV; modern newly renovated bathroom; full kitchen with a coffee maker, kettle, fridge, stove/oven and microwave; and a washer/dryer.

Top Guest favourite
A serene view showcases the landscaped yard, featuring blooming pink flower clusters in the foreground. A large tree stands in the center with a backdrop of greenery and a peaceful waterway. The two nearby structures are connected by a deck, reflecting the tranquil surroundings.
Apartment in Essex
4.97 out of 5 average rating, 287 reviews

A unique place on sue creek

Enjoy your private apartment and deck on the water or come sit down by the waterfront and watch the Ospreys, herons, ducks and the occasional eagle. Fishing off the pier and possible small boat docking available. We are close to Rocky Point golf club, Baltimore yacht club, 20 minutes from Camden Yards and M&T stadium. We are 38 minutes from BWI. You will have private parking in a quiet safe neighborhood. Sorry, no pets allowed.

Guest favourite
A cozy living area features a brown leather sofa next to a white coffee table. A decorative rug with star patterns lies on the floor. A green potted plant adds a natural touch, complemented by a television on a media unit. Light enters from the window.
Apartment in Chester
4.96 out of 5 average rating, 277 reviews

Cozy Waterfront Apartment Chester, MD

Hello travelers!! Looking for a cozy & comfortable place to stay on Kent Island? Come enjoy our clean & beautifully renovated apartment above our family home, overlooking Cox Creek. This apt. Is built above our garage. Private entrance on the side of our house (20 steep steps up). 1 bedroom, queen bed. WiFi included. Private porch to enjoy water view!

Popular amenities for Annapolis apartment rentals

When is the best time to visit Annapolis?

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Avg. price$291 NZD$272 NZD$291 NZD$322 NZD$363 NZD$334 NZD$354 NZD$334 NZD$361 NZD$413 NZD$327 NZD$301 NZD
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Quick stats about apartment rentals in Annapolis

  • Total holiday rentals

    Explore 90 holiday rentals in Annapolis

  • Nightly prices starting at

    Annapolis holiday rentals start at $86 NZD per night before taxes and fees

  • Verified guest reviews

    Over 6,240 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Annapolis holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Annapolis rentals

  • 4.9 Average rating

    Annapolis stays are highly rated by guests—averaging 4.9 out of 5!

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