Guest house holiday rentals in Southern Maryland

Delaney’s Compound- Peaceful Respite on the Point!

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!

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.

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.)

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.

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.

Patuxent River View

🌊 Nestled near North Beach, Herrington Harbor, Herrington on the Bay, and Chesapeake Beach, this serene guest house offers a peaceful escape for travelers of all kinds—whether you’re exploring local sights, reconnecting with nature, visiting family, or just passing through. Guests enjoy thoughtful amenities at no extra cost: a fully stocked kitchen, complimentary coffee and tea, high-speed WiFi, a pool and gazebo, and more comforts to make you feel right at home.

The Nichols House Cottage

This lovely guest cottage is located in the historic district of Oxford, walkable to town attractions and restaurants. While the main house is a registered historical property built in the 19th century Victorian style, the guesthouse is charming and well decorated with modern comforts. The cottage is completely independent from the main house. Make this your special place for a romantic getaway at any season of the year.

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.

Charming Studio with Free Parking & Private Entry

Our guest studio offers a cozy, relaxing getaway with a full-size bed, large walk-in shower, kitchenette with breakfast nook, and high-speed WiFi. Located just a 5-minute walk from Huntington Metro, 5-10 minute walk to Aldi & PJ’s Coffee, and a 10-minute drive to Old Town, it’s also close to local restaurants and shops. Enjoy a private entrance and 2 free on-site parking spaces for easy access. VA Permit #: STL-2024-00079.