Apartment holiday rentals in Southern Maryland

Our Little Piece of Heaven

Our cozy studio apartment sets on the Patuxent River. With the perfect views of Myrtle Beach, Point Patient and Thomas Johnson Bridge. Relax watching the boats and birds or take a walk along the water for a lovely neighborhood to stroll for 2.5 miles. Your favorite moments may be when you wake to see the sun rise and again to see the orange sky set. Just over the bridge from the popular Solomon's Island which is full of fabulous restaurants, boat rentals, charter fishing and summer concerts.

Apartment for 4 close to Ashland, RIR & The Meadow

This is a townhouse apartment located almost directly across the road from the historic Hanover Courthouse, and just a short walk from the historic Hanover Tavern. There are two bedrooms with queen beds, and one bathroom, all upstairs. Parking is free and directly in front of the apartment. There is one Smart TV with DISH network, Netflix, and Peacock streaming. WiFi is also included. There is a fully equipped kitchen and a coffee bar with a Keurig coffee pot. No smoking or vaping is allowed

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.

Walk to famous Tiki Bar on Solomons Island!

Cute studio apartment on charming Solomons Island. Walking distance to restaurants, live music, boat and kayak rentals. The kitchen has a full sized refrigerator, microwave, toaster, two burner cooktop,coffee maker & electric kettle We provide all bedding and bath towels for two people. Enjoy your coffee ( provided) or wine on the deck in the fenced in side yard. One well-behaved pet is welcome. Please make sure you pay the pet fee. We also have a boat slip across the street that you can rent

Spacious Beach House Top Floors - Walk Everywhere!

This booking is for the entire SECOND story & loft of a DUPLEX-style beach house. Entrance, access, & all indoor spaces of the unit are private, however there are often other guests and families on the first floor. There is also a STAIRCASE to the 2nd floor unit and a STAIRCASE to the loft. Please ensure this home suits your needs. The space has an open floor design with 14' cathedral ceilings for a spacious modern feel with beach-house charm. Walk 2 blocks to the beach, boardwalk, and more!

Retreat at Fenwick

This cozy one bedroom apartment is the perfect place to unwind & relax. Located in the heart of downtown Leonardtown, the Retreat at Fenwick is steps away from many delicious dining opportunities, unique and fun shopping at local boutiques, and entertainment experiences. It includes free wifi, a full kitchen & complimentary coffee bar, a charming eat-in dining space, queen size bed, full size pull out sofa bed, a cozy electric fireplace, workspace, and twin bunkbeds that are great for kids!

Luminous Architectural Gem

This luxurious space is filled with natural light streaming through the large windows. Exposed beams create a warm atmosphere. The open plan layout maximizes functionality, featuring a sleek modern kitchenette, a comfortable king size bed, and a stylish living area with a plush sofa and smart TV. The bathroom is crisp and contemporary with premium fixtures. Perfect for solo travelers or couples, the bright, beam-accented retreat offers a blend of comfort and character in an intimate setting.

Historic St. Mary's City, MD

1,000 square foot two-bedroom, one bath waterfront apartment features separate entrance and a screened-in porch overlooking the St. Mary’s River. Property has a large dock and a small private beach. Jellyfish, crabs, and oysters make swimming challenging, although many swim off the dock in the deeper water. No Diving! Dogs are welcome. We just ask that they be on a leash. The apartment is attached to part of the house where we reside, although it is sealed off and nothing is shared.

Ashland Aerie

Relax in this peaceful, stylish space for one, located north of Richmond. Park in the carport and go upstairs (21 steps) to enjoy privacy, convenience, and safety - with kitchenette, small washer/dryer, smart TV, desk, and exterior cameras. Ashland, less than three miles south, has restaurants (many), grocery stores, laundromats, a movie theater, a public library, churches, a post office, and Randolph Macon College. King’s Dominion and Meadow Event Park are six miles north.

Blue Crab Lodge

Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right above the delightful aroma of freshly brewed coffee, this unique and inviting space offers the perfect blend of comfort and convenience. Stepping outside, you'll find yourself in the heart of St. Michaels' quaint streets. The rental's prime location provides easy access to the town's boutique shops, waterfront promenades, and a diverse array of restaurants.

Serenity Suite on Chesapeake Bay

Come enjoy our waterfront home on the scenic Calvert Cliffs. Take in beautiful Bay views in Adirondack chairs with stunning vistas. Photograph wildlife. Comfortable ½ mile walk to private community bay shoreline. Have breakfast in the yard while enjoying the sunrise. Stroll the community shoreline and explore fossil hunting, hike at nearby trails. No pets are allowed because I have a severe allergic reaction to pet hair and dander. Thanks for your understanding.

Apartment, centrally located Historic DnTwnFXBG!

Welcome to downtown Fredericksburg's historic district! This charming 1st-floor apartment (~500 sqft) sleeps up to 4 with a modern-boho vibe. Enjoy a full kitchen, spacious living & dining area, and a large TV for unwinding. Steps from Caroline Street's shops, restaurants, and galleries — no car needed! Self check-in via smart lock makes arrival easy. Perfect for couples, small families, or a solo getaway in one of Virginia's most walkable historic towns.