Guest house holiday rentals in Southern Maryland

Private Art-Filled Guesthouse near Naval Academy

Slip under a colorful quilt and get a great night's sleep in a secluded walk-up guesthouse. An intriguing blend of antique curios and Americana populates the room. The result is a comforting space that also has a modern kitchen and updated bathroom. Homeowners on site and available to book your Treetop Getaway! Key code access will be provided. Check in time is 3pm. Check out time is 11am. Contact me via phone or through messages here and I will respond as soon as possible. The guesthouse is in West Annapolis, a residential neighborhood bounded by Weems Creek and the Severn River. It's close to downtown, the Naval Academy, and the Stadium. Quaint shops and restaurants are just around the corner.

Delaney’s Compound-Book now for Summer!

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!

Patuxent River View

🏡Stay at this peaceful, amenity‑rich guest house near North Beach, Chesapeake Beach, and Herrington Harbour, with quick access to Washington, DC, Baltimore, and Annapolis. Enjoy a fully stocked kitchen, coffee, fast WiFi, a seasonal pool, and a shaded gazebo designed for comfort and convenience. Perfect for wedding weekends, family visits, work trips, and quiet coastal getaways, this cozy home base makes it easy to relax, cook, stream, and recharge between festivities and exploring the area.

Waterfront Guesthouse I on the Rappahannock

The “Bay House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has a beautiful Bay view and includes access to our private beach & dock (w/ guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath w/ jetted tub, covered patio and carport. The 2nd floor features a large bedroom, king bed and 1/2 bath.

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.

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.

2 Bdrms★Pet Friendly★4K Theater★Fire Pit★Fast Wifi

Minutes from I-95 "The Cottage" is a great stop along your journey & 15 minutes to Kings Dominion or Meadow Event Park. Surf high speed internet, catch up on laundry, dine in Ashland or have a cookout and share stories around the campfire. You’ll love the Cottage because of the clean accommodations, complete kitchen, quiet neighborhood, home theater, comfy beds, no cleaning fee & pet friendly! The Cottage is great for Families, Couples, Business Travelers & Fun Seekers!

Private Sunny Cottage with King Bed + Yard / Patio

Welcome to Bagelot! Location! Location! Location! Nestled in the heart of Arlington, VA (extremely safe and ranked as one of the best cities for biking) -- just a quick car ride, moderate bike ride, or long walk into DC (Georgetown waterfront!) -- with spacious lawn and patio areas for lounging, grilling, sports, etc., this brand new cottage with high ceilings and lofted bedroom is the oasis within the city and home away from home you've been dreaming about!

Waterfront-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.

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.