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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, 505 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
A serene view of the Chester River is presented, with soft pink clouds reflecting the sunset hues. Docked boats are visible along the wooden dock, while lush greenery frames the scene, providing a peaceful atmosphere at twilight.
Flat in Grasonville
4.9 out of 5 average rating, 219 reviews

Halcyon house. Lovely views on MD eastern shore.

This charming apartment is located on the Chester river on Maryland's Eastern Shore. The wildlife is abundant and generally very active. The sun rise and sunsets can be spectacular. The property is 20 minutes from Annapolis and 50 minutes from DC. The newly renovated apartment has all new appliances and a well stocked kitchen with many herbs and spices, condiments, coffee, tea, cream and sugar etc. The 8 mile long Cross Island Trail starts a block from the house and leads to several restaurant

Guest favourite
A bright and airy living space features a cozy blue loveseat, a clean white coffee table, and two high-backed stools at a counter. A kitchenette is visible with modern appliances, including a microwave and mini-fridge. Natural light floods through a large window, accented by greenery.
Flat in Petworth
4.96 out of 5 average rating, 201 reviews

Bright and Airy Private Apt -Two Blocks from Metro

Stay in this chic and stylish private, basement studio apartment during your visit to Washington, DC. Our place has been recently renovated and features lots of light, a spa-like bathroom, a kitchenette, and a private entrance with a Smart Lock. The space is crisp and clean. Perfect for 2 people. The apartment is located two blocks from the Petworth metro station and near several bus lines. Use public transportation to get to the National Mall in 25 minutes or drive in 15! FREE STREET PARKING!

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, 118 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, 152 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 cozy living room features a leather couch with a decorative throw pillow, paired with a wooden coffee table holding a woven basket of tissue and other items. A light-colored chair sits nearby, and a dining table with four chairs is against the wall, illuminated by natural light from a window.
Flat in Capitol Hill
4.85 out of 5 average rating, 191 reviews

Capitol Hill Basement Apartment - Private Parking

Welcome to DC's Capitol Hill! If you’re looking for a quiet, neighborhood feel, with easy access to all that DC has to offer, then this apartment is for you. This 1BR/1BA unit is in a historic district, on a quaint residential street that's walking distance to attractions like Lincoln Park, H Street Corridor, and Eastern Market. It’s just one block to a bus stop and a half mile to the Metro, putting sites like the U.S. Capitol, Library of Congress and Supreme Court right at your fingertips!

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, 110 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
A king bed is dressed in a richly colored quilt featuring intricate patterns of gold and purple. Two decorative pillows add texture, while the exposed brick wall provides a historic backdrop. A bedside lamp casts a warm glow on the space.
Flat in Annapolis
4.88 out of 5 average rating, 101 reviews

Charming 18th C. Apt in DTA

Lower level furnished apartment in one of Historic Annapolis's 10 oldest private residences. Boasts lovely wood, brick & ornamental ironwork Covered keyless entry King Henredon bed Exec desk & chair TV w/ Roku Decorative fireplace Iron & board Robe & slippers Claw foot tub w/ shower Beverage station (coffee maker,mugs wine&bottle opener, glasses, ice bucket, flutes) Microwave Fridge/freezer Cutlery Plates & napkins Bistro table & stools for 2 Limited free street parking 8p-8a

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, 115 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.
Flat in Hyattsville
4.84 out of 5 average rating, 342 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.
Flat in Annapolis
4.76 out of 5 average rating, 291 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
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, 289 reviews

A place unique 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.

Popular amenities for Annapolis apartment rentals

When is the best time to visit Annapolis?

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Avg. price$217 SGD$203 SGD$217 SGD$240 SGD$271 SGD$249 SGD$264 SGD$249 SGD$269 SGD$296 SGD$253 SGD$244 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 $64 SGD per night before taxes and fees

  • Verified guest reviews

    Over 6,350 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

  • Holiday rentals with a pool

    10 properties feature pools

  • 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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