Apartment holiday rentals in Annapolis

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Top-rated apartment rentals in Annapolis

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Guest favourite
A comfortable seating area features a large sectional sofa adorned with colorful throw pillows. A round table sits in the center atop a decorative area rug. Natural light streams in through wide windows, complemented by a floor lamp and a touch of greenery from plants.
Apartment in Logan Circle
4.9 out of 5 average rating, 583 reviews

Gorgeous, large, modern 1 BR on Hist. Logan Circle

Gorgeous, bright, open plan nearly 1,000 square foot 1 bedroom condo with space for an entire family in historic Logan Circle neighborhood on a quiet street. Short walk to White House, Mall & museums. Built in 1900, this brownstone was thoughtfully renovated to blend modern (in-ceiling lighting, stainless steel appliances, bamboo flooring) with historic features (original exposed brick & trim). Warm, spacious & comfortable for your stay. Logan is DC's hottest & hippest area with a 96 walk score.

Superhost
A bright living area features a gray sofa with patterned cushions, complemented by a cozy armchair. A trio of small, round tables sits on a soft area rug. Floor-to-ceiling windows allow natural light to illuminate the space, framed by light blue curtains.
Apartment in Penrose
4.89 out of 5 average rating, 296 reviews

Newly Renovated & Modern 1BR Condo - Unit 4

Completely renovated, stylishly furnished condo unit in Arlington, VA just one stoplight from Washington DC, the Pentagon, Clarendon, Crystal City & National Airport. Spacious unit with free cable TV, secure Internet/Wi-Fi, FREE reserved PARKING space in private lot, in-unit Washer/Dryer, Full Kitchen. Steps away from public transit buses that route to multiple Orange/Blue/Silver line Metro trains. Comfortably accommodates the traveling professional, those on vacation and is kid friendly.

Top guest favourite
A welcoming living area features a light-colored sofa and an upholstered armchair, positioned around a central wooden coffee table. A unique area rug with intricate patterns adds warmth. The kitchen area, visible in the background, is equipped with modern appliances and a breakfast bar with stools.
Apartment in Annapolis
4.96 out of 5 average rating, 112 reviews

Funky Uptown Apt meets Downtown - Hist District

Location location location where Uptown meets Downtown in the Historic District. 1/2 block to Dinner Under The ✨ , First Sunday Arts. Tsu, 49 West, Level in the front yard Ramshead, Stan and Joes and Reynold's Tavern in the back. EVERYTHING Annapolis (USNA, Stadium, Statehouse, Ego Alley, Main St, Eastport) is walking distance from this unique 2nd floor unit w elevated deck for morning coffee as Jazz wafts in, full kitchen, w/d, clawfoot shower/tub, MBR with Queen, BR2 with Full. LR w/sofa

Guest favourite
A spacious living area is depicted with plush teal seating arranged around a coffee table. A modern entertainment unit is positioned against a wall, while large sliding doors open to a private balcony. Natural light enhances the warm tones of the decor.
Apartment in Annapolis
4.97 out of 5 average rating, 118 reviews

1 bedroom -king in Annapolis- low cleaning fee

Brand New Vacation Rental – Prime Annapolis Location! 1 bedroom. Experience the best of Annapolis in this newly renovated, beautifully furnished 1-bedroom condo with a king bed and NO chore list! This open-concept retreat offers a bright, modern interior and a private balcony to unwind. Start your day with a scenic walk through Truxton Park trails or head to the boat ramp to catch a water taxi to downtown Annapolis! Whether you're here for relaxation or adventure, this is the perfect spot.

Top guest favourite
Apartment in Baltimore
4.98 out of 5 average rating, 143 reviews

Moon Base in Hampden Complete w/Movie Projector!

Artists and creatives are welcomed! Stay at our 1920 rowhouse with its mix of 70's era textiles and contemporary style. Please enter the shared hallway and find the entrance to your apartment on the right. Across from the coat rack. Moon Base (ment) is the lower level private full apartment, with fully stocked kitchen w/electric cooktop dishwasher, garbage disposal, comfy double bed, private bath w/shower, laundry and your own patio off the kitchen and access to small patio with lighting.

Top guest favourite
Apartment in Annapolis
4.96 out of 5 average rating, 323 reviews

Annapolis Waterfront Condo - Unit #: A-203

Cozy, comfortable condo. Great views - 2nd flr. Fireplace 1 bed/bath condo, sleeps 4 max, covered, water front deck, reserved parking! .5 mile walk to dwnt Annapolis and the Naval Academy, 1.9mi to the Navy stadium. Book NOW for the Summer! Easy access to Spring/Fall boatshows. 12 stairs, no elevator. Pool Memorial to Labor Day: MWTh 4pm-8 Tues: Closed FSS and Holidays: 12pm-8 The pool is one of the best places to be on a hot summer day. If hours are unacceptable, pls select another

Top guest favourite
The living area features a modern black sofa and two white accent chairs positioned around a circular coffee table. A wall-mounted television is above a sleek electric fireplace, complemented by decorative shelves with small plants. Natural light filters through wooden blinds.
Apartment in National Harbor
4.9 out of 5 average rating, 177 reviews

Luxury Living at National Harbor

Spacious Condo in the Heart of National Harbor! Experience comfort and convenience in this stylish one-bedroom apartment with a den, which can be converted into a second bedroom (Air mattress queen size) upon request. Located in the vibrant National Harbor, this condo offers an open-concept design and is surrounded by an exciting mix of restaurants, bars, shops, and entertainment options for all ages. This is your perfect home base for exploring Washington, D.C. and its surroundings.

Guest favourite
A cozy living area is highlighted by a large 65" TV on a white media console, flanked by tall speakers. A soft sofa is paired with a round dining table set for two, complemented by a potted plant and framed artwork on the wall.
Apartment in Petworth
4.91 out of 5 average rating, 249 reviews

New, Sunny, 2BR - Parking, Patio, Firepit

Sunny, newly renovated, pet friendly 2BR apartment available in the trendy Petworth neighborhood with full designer kitchen and bathroom, home theatre surround sound setup with 65" TV, washer/dryer, and permit parking included! Safe, friendly, picturesque neighborhood; it's tree-lined streets are mere blocks from the award winning restaurants on Upshur St. Located only .9 miles from the Petworth and Fort Totten Metro stations, and 3 miles from the White House and downtown DC.

Guest favourite
A wooden walkway extends along the water, bordered by low posts and a railing. Boats are docked in the distance, with a gentle curve of the marina visible. Potted plants and striped decor can be seen, contributing to the waterfront atmosphere.
Apartment in Annapolis
4.89 out of 5 average rating, 128 reviews

Annapolis @Gate 1 steps to the Harbor Free parking

Parking included. The heart of Annapolis 1 street from the harbor, fun restaurants & backs to the Naval Academy. This 1st floor 2 bed / 1 ba condo has been fully renovated with new paint, floors, bath & kitchen. 1 Parking space included & additional paid parking on street. Queen Bed & sleeper couch is a full size. Linens included. Kitchen includes refrigerator, stove/oven, microwave, keurig, dishes silverware, pots and pans. High speed internet included & separate work area.

Top guest favourite
A bright living area features stylish seating arrangements with two blue sofas and a central ottoman. A wall-mounted television is positioned beneath decorative shelving. An open kitchen space is visible, showcasing modern bar stools and a dining area bathed in natural light from a nearby window.
Apartment in Annapolis
4.94 out of 5 average rating, 433 reviews

Renovated Apt In Historic Dist w/2 Parking Spots

Renovated upstairs unit two bedroom with TWO parking spots in the Historic District. Everything is high end and used exclusively as a short term rental. Private entrance, cute small custom kitchen, ceiling fans, mini split AC/ heat in every room for year round comfort. Hardwood floors, quality linens , lucid mattresses, Keurig coffee bar, toiletries. Walk to town in 10 min or less or take the free trolley to Main St, USNA, Churches, AYC. No children under 12.

Guest favourite
Apartment in Trinidad
4.94 out of 5 average rating, 193 reviews

Modern, spotless 1br for families or work

Bright and unique basement gem in the heart of DC! This thoughtfully renovated private space gets sunlight in the front and rear through real windows and glass doors. Enjoy your morning coffee on your own private patio. Come and go easily with your dedicated gated parking spot (free parking, off street!). Enjoy a full kitchen. Working during your stay? We have fast wi-fi. Live like a local in a (relatively) quiet residential neighborhood.

Top guest favourite
A living area features a gray couch adorned with decorative pillows against a light wall. A recliner is positioned nearby, and a wall-mounted Smart TV is visible. A dresser with a plant sits below the TV. Natural light streams in through nearby windows.
Apartment in Annapolis
4.95 out of 5 average rating, 131 reviews

1st Floor Condo in Annapolis

This newly renovated, 1st floor studio is perfectly located just across Spa Creek from historic Annapolis in Eastport. Within easy walking distance of restaurants (3 min), Main Street/City Dock (10 min) & USNA's Gate 1 entrance (14 min), our studio includes a full kitchen, high-speed wifi, free onsite parking lot, a secure building entrance, dock and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

Popular amenities for Annapolis apartment rentals

When is the best time to visit Annapolis?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$221 SGD$199 SGD$206 SGD$217 SGD$255 SGD$232 SGD$236 SGD$246 SGD$242 SGD$256 SGD$273 SGD$259 SGD
Avg. temp1°C3°C7°C13°C18°C23°C26°C25°C21°C14°C8°C4°C

Quick stats about apartment rentals in Annapolis

  • Total holiday rentals

    Explore 20 holiday rentals in Annapolis

  • Nightly prices starting at

    Annapolis holiday rentals start at $76 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,070 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Annapolis holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Annapolis rentals

  • 4.8 Average rating

    Annapolis stays are highly rated by guests – averaging 4.8 out of 5!

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