Guest house holiday rentals in Southern Maryland

Delaney’s Compound-Deeply discounted monthly stays

Delaney’s Compound Guest House accommodates up to 4 guests. Dogs are welcome with pre-approval & $75 fee (for 1st pet). A small fenced yard keeps them safe! The Guest House was built using reclaimed lumber & other charming elements from the original farmhouse outbuilding (circa 1889). There’s a cozy fireplace for snuggling and a second floor balcony for coffee or cocktails. The front yard has a fire pit and river views. The Guest House is sparkling clean, fully furnished & ready to welcome you!

2 Level Delight! Sights, Eats, Museums+Pkg

Stay in the heart of Historic Capitol Hill at this fabulous 2-level Carriage House, offering the perfect blend of charm, privacy, and unbeatable location in Washington, DC. 5 beautiful blocks from Union Station, you’ll be within easy walking distance to the Capitol Bldg, top-rated restaurants, parks, & everything the city has to offer—all while enjoying the quiet comfort of your own private retreat. Explore, work, or relax, this is the perfect home away from home for your next DC adventure.

Casita Del Ray — Alexandria Studio Apartment

Welcome to Casita Del Ray! Location is everything, and this location doesn't disappoint! Situated in the charming neighborhood of Del Ray, "Where Main Street Still Exists," the Casita is a quiet oasis. From the Casita, you can walk to Del Ray's magical main street, which features restaurants, shops and activities. And the best part? You're only 10 minutes from DC! If DC isn't your thing, Arlington and Old Town Alexandria are also just a few miles away. We would love to host you soon.

Sunny, Stylish Carriage House with a View

Welcome to my private carriage house retreat! This stylish and quiet guesthouse with a blend of old farmhouse and modern features is a block from the heart of the Del Ray neighborhood. Separate from the owner’s home, the sunny second-floor guesthouse combines privacy, style, and convenience to nearby shops and restaurants. Features a kitchenette, stylish sitting and bedroom with tons of light, heart pine floors, bathroom with radiant floor heating, high-speed internet, and ample storage.

Vibrant + Artsy - mins to NavyYard, CapHill, Dtown

1 bed 1 bath bright artsy basement unit with private rear (alley) entrance in colorful urban Anacostia neighborhood. Short term rental created to be your home away from home for however long you stay. Conveniently located 2 blocks to multiple bus stops, 1 mile from Anacostia Metro station, and a 10-minute ride to Downtown DC. Sleeps up to 5 but most optimal for 2 people. (Starting July 13, the space will only be available for up to 4 people as the yellow futon sofa will be removed.)

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

Urban Cottage, MD minutes from DC/National Harbor

Come and enjoy our spacious detached cottage,lounge on your private back deck overlooking private parkland forests. A real urban escape in an excellent location! Just a few blocks away from the MGM Resort / Casino, National Harbor, and shopping. Across the river from historic Alexandria and 10-minutes from Washington,DC. Great for a solo adventure,couples,and friends (up to 4 guests). Enjoy the seasonal steam house and personal wood-burning stove if you book in the cold months.

Cozy Studio Retreat

This charming and cozy room is thoughtfully designed for comfort and relaxation. The room has it's own private entrance and features a cozy plush queen bed, kitchenette and full bath. Enjoy the warm, inviting atmosphere with soft lighting, and curated touches that make it feel like home. Ideal for solo travelers or couples, this space is located in a quiet neighborhood, close to local attractions, restaurants, Wi-Fi, free parking, and complimentary coffee/ tea are included.

Little House by the water

Serenity - Privacy - Beauty - This little house by the water has it all. New Sealy queen size mattress, well equipped kitchen, Cuisinart coffee maker, full oven, glass topped stove, new refrigerator, and fully screened porch with water view. Perfect for 1 or 2 adults looking to get off the grid and recharge. In St. Mary's County,MD, just 90 minutes south of Washington DC. However, the space is small and it is really a studio apartment as I think the pictures make evident.

Renovated Basement with Private Entrance

Fully renovated & updated basement with a full set of windows and sunlight. House is in a very nice and safe neighborhood. Walk-out basement with Private Entrance. Plenty of Parking. Non smoking. All Utilities and Wi-Fi are included. • Total Area: 800 Sq.ft. • One Bedroom with closet • Full Bathroom • Fully Furnished • Kitchen • Dining Area • Walk out Basement – Above ground (Private Entrance) • No Owen • No Dishwasher • No Washer and Dryer • Plenty of Parking • No Smoking

Waterfront-View of Bay from your Bed-Steamy Sauna

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Studio on the Bay.

This studio apartment is in walking or driving distance to three private beaches in our community. There is 1 bedroom with a queen size bed, spacious bathroom and closet. The living room has a pull out full size bed and a kitchenette. Coffee, teas, beach chairs, are provided. Wanna fish??? Ask Joey about Fish Taxi! Fifteen minutes from Solomons Island (home of the Tiki Bar). An hour or so from DC, Annapolis and Waldorf.