Guesthouse holiday rentals in Southern Maryland

Find and book unique guesthouse rentals on Airbnb

Top-rated Guesthouses in Southern Maryland

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Top Guest favourite

Guesthouse in Colonial Beach

4.93 out of 5 average rating, 120 reviews

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!

Guest favourite

Guesthouse in Alexandria

4.85 out of 5 average rating, 381 reviews

Adorable 1-Bedroom guesthouse with free parking

Take it easy at this unique and tranquil getaway. Enjoy the quiet, stylish, and beautiful land. The place is located mile away from Metro, walking distance to shopping centers. It is 3 miles away from Downtown Alexandria, and 8 miles away from the White House or National Mall. Ideal for 2 or 3 people. 1 king bed and I sofa bed available. Parking on the garden is free of charge. You have everything you need in the house to relax and enjoy your stay. No cleaning charge which is extra saving!

Guest favourite

Guesthouse in Alexandria

4.93 out of 5 average rating, 106 reviews

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.

Top Guest favourite

Guesthouse in Cambridge

4.99 out of 5 average rating, 130 reviews

Rosses Chance Guest House

This lovely guest cottage is located on a historic 16 acre waterfront estate on Hudson Creek that includes a main house, barn, pool, dock and pond. Built in the 18th century tidewater style, the guesthouse is charming and well decorated and completely self efficient. A special place for your romantic getaway at any season of the year. Recently cell phone service has improved and is reliable. However, in the country, WiFi internetl can be slow at times as well as the Wifi TV streaming.

Top Guest favourite

Guesthouse in Easton

4.99 out of 5 average rating, 622 reviews

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.

Guest favourite

Guesthouse in Fort Washington

4.93 out of 5 average rating, 747 reviews

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.

Top Guest favourite

Guesthouse in Bushwood

4.93 out of 5 average rating, 165 reviews

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.

Guest favourite

Guesthouse in Owings

4.92 out of 5 average rating, 118 reviews

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.

Top Guest favourite

Guesthouse in Stevensville

4.99 out of 5 average rating, 309 reviews

Waterfront Getaway - View of bay from your bed

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.

Top Guest favourite

Guesthouse in Saint Leonard

4.97 out of 5 average rating, 116 reviews

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.

Guest favourite

Guesthouse in Arlington

4.81 out of 5 average rating, 147 reviews

Hidden Gem Minutes from DC and Airports

Stylishly designed homage to a lake cabin with cedar walls and ceiling, radiant heated floors, skylights, custom shelving and cabinets, a steam shower, and an upscale kitchen. An entire wall of glass doors opens to the backyard bringing the outside in. Hidden location yet easily accessible to everything! Near restaurants, grocery store, Pentagon with arteries leading to DC, Crystal City, and area airports are within minutes.

Top Guest favourite

Guesthouse in Washington

4.99 out of 5 average rating, 416 reviews

Private, quiet mini-house on the Hill! Near Metro.

Mini-house on Capitol Hill! Super clean, fast wifi, fresh linens, fully-equipped kitchen with private patio. We offer a neighborhood parking pass and street parking is easy. Three blocks from metro and 3 bike share stations nearby. Great grocery stores too. Nice Safeway and Trader Joe's within walking distance and a Whole Foods a bit further. Easy walk to Eastern Market too. Great launch spot for all that DC has to offer.