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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.
Flat in Annapolis
4.92 out of 5 average rating, 501 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.
Flat in Sykesville
4.95 out of 5 average rating, 212 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.

Top guest favourite
A modern living area features a light-colored sofa adorned with a teal throw blanket. A round wooden table accompanied by metal chairs is positioned nearby. A decorative mirror and an abstract painting are displayed on the wall, while a stone fireplace adds a subtle touch of warmth.
Flat in Stevensville
4.98 out of 5 average rating, 295 reviews

Boutique by the Bay

Completely renovated and exquisitely decorated, this one bedroom apartment has a private entrance from the main house and features a modern farmhouse vibe. Fully equipped kitchen with new glass top stove, large walk-in shower and queen sleeper sofa make this perfect for a couple or family. Located 9 miles south of the Bay Bridge, off of Route 8 on Kent Point Road ,this location is convenient for weddings at the Chesapeake Bay Beach Club or Swan Cove. Access to large in-ground pool included.

Top guest favourite
The historic building features a distinctive red brick façade, complemented by large windows and decorative trim. Lush green trees provide shade in front, while parked vehicles line the street, enhancing the inviting urban atmosphere.
Flat in Butchers Hill
4.98 out of 5 average rating, 456 reviews

Butchershill- Clean, Fireplace, King Bed, Parking!

My name is John S Marsiglia. Always clean, very comfortable new King Mattress, Warm & Cozy Fireplace, Self checkin , Historic 2207 E Baltimore St. Search online. 900 Sq Ft. 12 ft ceilings,Fully equipped kitchen/kitchenette,Coffee,Tea,Cream,Brita filtered water pitcher,50" 4K smart TV, streaming only, Free Netflix, Prime,top speed WiFi, surround sound, comfortable clean furniture, antiques, oriental rugs, workspace w/desk, modern beautiful bathroom, dual shower heads&seats, private full size W&D

Top guest favourite
A charming corner of a historic building is showcased, featuring a prominent American flag flanked by potted greenery. The view extends down a quiet street, with a glimpse of an adjacent building in the background, enhancing the setting of Annapolis's historic district.
Flat in Annapolis
4.99 out of 5 average rating, 117 reviews

CIRCA 1885-Historic Annapolis-USNA GATE 1

A stunning home, "Circa 1885" is a restored piece of Annapolis history. Sitting at one of the two major gateways that lead to downtown, our beautifully renovated home sits on the corner of King George and Randall Streets. A distinctive yellow PRIVATE entry door at 4 Randall Street leads to this rental apartment that boasts 2 large bedrooms (K,Q), family room with pull out sofa, 1 bath with antique claw foot tub/shower and a full eat in kitchen. Everything Annapolis is within a 2 block walk.

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.
Flat in Bowie
4.93 out of 5 average rating, 143 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)

Guest favourite
A charming exterior is displayed, featuring a white wooden facade and a welcoming entrance. A brick pathway leads to the door, which is illuminated by a warm light fixture. Decorative greenery frames the doorway, enhancing the home's inviting character.
Flat in Annapolis
4.93 out of 5 average rating, 107 reviews

Historic Annapolis Rental Minutes from Downtown

Immerse yourself in all Annapolis has to offer in this newly restored historic home. This charming rental neighbors the Naval Academy and is just a 5 minute walk to the heart of downtown Annapolis. This home has 2 bedroom and 1 full bath. This is the perfect place to stay whether you're looking to explore historic Annapolis, the Naval Academy grounds, or even taking a day trip to Washington D.C. Inside the home you'll find cozy furniture, new finishing's, and wifi throughout the house.

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.
Flat in Annapolis
4.92 out of 5 average rating, 111 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
A serene waterfront scene is captured at sunset, displaying calm water reflecting soft hues of orange and blue. Silhouettes of trees line the shore, while gentle ripples can be seen across the surface, creating a peaceful atmosphere.
Flat in Deale
4.91 out of 5 average rating, 620 reviews

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise

Gift yourself this private, secluded second floor Flat & Solarium Bedroom. Best hideaway to rest, bond, restore, create, or work. A breezy, country-like setting provides space to escape the city hustle! Nearby scenic drives & groceries, or venture to Annapolis TJ/WF or historic walks. Fully relax with pier, kayaks, swings, fire pit, starry nights, sun-drenched loungers, cozy up with books/movies & luxuriate in the deep soaking tub or European shower.

Guest favourite
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.
Flat in Annapolis
4.78 out of 5 average rating, 284 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".

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.
Flat in Essex
4.97 out of 5 average rating, 284 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 colorful two-story building is presented, featuring bright blue siding and white trim around the windows. The entrance is marked by pink doors, and a red sign indicates a business within. Nearby streets and a gated area are visible, creating a lively atmosphere.
Flat in Annapolis
4.9 out of 5 average rating, 165 reviews

Eight Fleet - Annapolis Dock

Welcome to city dock, the heart of historic downtown Annapolis! We are steps from the Maryland State House, US Naval Academy, St. John's College, the Annapolis Arts District, and a wide variety of restaurants, pubs and shopping. This 3-bedroom apartment provides a uniquely fun yet businesslike environment for your stay, in a town where military meets artsy.

Popular amenities for Annapolis apartment rentals

When is the best time to visit Annapolis?

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Avg. price$221 SGD$207 SGD$221 SGD$245 SGD$276 SGD$254 SGD$269 SGD$254 SGD$275 SGD$314 SGD$249 SGD$229 SGD
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Quick stats about flat rentals in Annapolis

  • Total holiday rentals

    Explore 90 holiday rentals in Annapolis

  • Nightly prices starting at

    Annapolis holiday rentals start at $65 SGD 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    90 of Annapolis holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi 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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