Condo holiday rentals in Anne Arundel County

4.94 out of 5 average rating, 405 reviews

Brand New Reno in Historic Dist w 2 Parking spots

Spotless / sanitized !! Renovated upstairs unit two bedroom with TWO parking spots in the Historic District. Everything is high end, brand new 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 10.

4.97 out of 5 average rating, 108 reviews

Welcome to Annapolis-very 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.

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Condo in Bowie

New place to stay

Work Home 2

Welcome to your perfect home away from home in the heart of Bowie, Maryland – ideal for families, business travelers, or anyone seeking peace, space, and proximity to the best of the DMV! This spacious 3-bedroom, 2.bath home offers everything you need for a relaxing stay – from a fully stocked kitchen and fast WiFi 🛏️ The Space: 3 Bedrooms 2 Bathrooms Full Kitchen – Stainless appliances, Keurig, cookware Cozy Living Room – Smart TV, streaming services, comfy couch Washer/Dryer

4.9 out of 5 average rating, 80 reviews

Condo in Hanover

Parkside Retreat Brand New 3-bedroom condo

The Parkside Retreat is a new 2-story condo located in a resort-style community that features a spacious kitchen/dining area, a 75" HD TV with 5.1 surround sound, three thoughtfully decorated bedrooms and 2 full baths / 1 half. The sprawling master suite features a walk-in closet, a luxurious king-size bed and a bathroom with a double-sink vanity, a shower and luxurious white bath towels. Best part? It is truly central to unlimited historical sites, restaurants, shopping and more!

4.98 out of 5 average rating, 153 reviews

New Downtown Annapolis Condo With Free Parking

This newly constructed property brings chic, low-maintenance living to the heart of Annapolis. No parties, events, or large gatherings! The week-long stay discount is 25%! The month-long stay discount is 40%! The early bird discount is 10% (12 months in advance) The last minute discount is 10% (28 days in advance) Pets are only $100 per stay! Additional guests are $15 per person per night :) We would be happy to accommodate flexible check-in and check-out times if available!

4.88 out of 5 average rating, 104 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.

4.84 out of 5 average rating, 73 reviews

Anchors Away

Eastport: Spacious studio boasts high ceilings & lots of natural light with his and hers walk-in closets. Fully remodeled with fresh paint, new floors, bath & kitchen. Tempur-pedic Murphy bed & cozy electric fireplace below a 58” 4K television. Basement houses additional storage & full-size W/D. Grill area. Free off-on street parking. Walking distance to Eastport's finest restaurants, or take the water taxi across Spa Creek into down-town Annapolis or the Naval Academy.

4.96 out of 5 average rating, 75 reviews

1st Floor Condo in Annapolis

This newly renovated, 1st floor studio is perfectly located just across Spa Creek from historic Annapolis in the quiet yet hip neighborhood of 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, a secure building entrance, dock access & a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

4.96 out of 5 average rating, 98 reviews

Funky Uptown Apt meets Downtown - Hist District

Location location location where Uptown meets Downtown in the Historic District. Tsunami, 49 West, Level in the front yard with Ramshead, Stan and Joes and Reynold's Tavern in the back. EVERYTHING Annapolis (USNA, Stadium, Statehouse, Ego Alley, Main St, Maryland Hall, Eastport) is walking distance from this unique 2nd floor unit w full kitchen, washer/dryer, clawfoot tub, deck, BR with full size bed, LR w/sofa. Short term parking to unload, garage pass for long term

4.95 out of 5 average rating, 22 reviews

Condo in Sparrows Point

The Industrial Suite

The Industrial R&R Suite is a wonderful, modern live/work space located in a commercial/residential building. Influenced by the historic Bethlehem Steel Mill. This unique place has a style all its own. Minutes from Tradepoint Atlantic, 695, 95, and Baltimore City however located in Baltimore County's best kept secret, the North Point Peninsula. Cave like bathroom is decked out in slate, antique brick, stone, concrete, and tile! Note: Rain Shower Head Height is only 6'!!

4.98 out of 5 average rating, 90 reviews

Charming Annapolis Waterfront Condo

Discover the charm of CAPTAINS QUARTERS, your exclusive waterfront retreat in the prestigious Yacht Club Condominiums. Steps from Downtown Eastport and Annapolis, this gem offers stunning views, a community pool, and the essence of luxury. With 2 free parking spots, you're 1.6 miles from the Naval Academy and under a mile to Downtown Annapolis attractions. Perfectly positioned for exploration or relaxation, your stay promises an unmatched Annapolis experience.