Holiday rentals in Crofton

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

Luxury 1BR/1BA Private Suite Close to DC!

Whether you’re looking for a place to stay a couple of days, weeks, or months, this luxurious basement apartment offers a spacious environment with the perfect touch of style, comfort, and sophistication. Enjoy the electric fireplace, office, reading nook, and your own private spa bathroom. This suite has a private entrance and is located in a very peaceful cul de sac with plenty of restaurants and shopping nearby. The home is located just 20 mins outside of DC. Not suitable for small children.

Waterfront Chesapeake Bay Sunrises & Fishing Pier!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Just Like Home - Private Entrance Apt in DMV Area

288 SQ FT PRIVATE ENTRANCE Mother-in-law suite/ studio apt, full bed, sleeper sofa, roll-away single bed, full kitchen, bathroom with small shower stall, 65” Smart TV w/cable, Netflix & WiFi. No guests under 12 years of age. Location: Ft. Meade (14.4 miles), Annapolis (15 m), Andrews AFB (19 m), Washington DC (19 m), Baltimore (29 m) Nearby airports: DCA (23 m), BWI (27 m), IAD (48 m) Public Transportation: Metro Bus Stop (0.2 m), New Carrollton Station Metrorail, Amtrak, & Greyhound (9 m)

In Town, Rock Hall, Fenced-In Yard, 1 blk to Water

In Town, Amazing Location on Walnut Street, Rock Hall Clean, Quiet & Beautiful Rancher, Large Fenced in Yard! 1 Bedroom (Queen) 1 Bedroom (Queen) Sun Room (Twin) Daybed Only 1 block from the Chesapeake Bay. Perfect for your weekend getaway or longer stay. Tastefully updated 2-bedroom, 1 bath ranch home. Located JUST one block from marinas, restaurants, Public Landing and Rock Hall Harbor. Three blocks from Ferry Park Beach. A beautiful and safe stroll or bike ride to Main Street (1.5 mile)

"Hilltop Hideaway"- Private basement suite

Location, location! "Hilltop Hideaway" is a private basement apartment just 16 miles from BWI airport, 10 miles from Fort Meade and Annapolis, and less than 30 miles to Baltimore and Washington, DC! Nestled in a wooded setting on 2 acres, it is perfect for 1-2 adults (25yrs old or older). Not suited for children. Offers living space, bathroom, kitchenette w/microwave, toaster oven, coffee maker, crock pot, apartment size fridge and separate dining nook. Private key code entrance and parking.

Chesapeake Comfort, Annapolis.

Veteran Superhost! Annapolis Bungalow Home. Professionally cleaned and a full time Airbnb. I have been a Superhost with my listings for over 10 years. Walking distance to Navy Stadium and to Park Place where you can jump on the trolley and take a ride through town. Enjoy the spacious backyard deck and yard. Bring your kayaks and store on our rack and walk it down to the launch. Queen Bedroom on ground floor. 2nd Queen Bedroom on lower level w/bathroom. Loft bedroom has 2 full size beds.

Lil’ House - A Serene Tiny Home Experience

Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

Weems Creek Cottage, Annapolis Waterfront

(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early. The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch. We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.

12 M to Naval Academy | Waterfront Paradise

Discover the perfect blend of tranquility and convenience at our charming waterfront property. Nestled away in a serene setting yet close to all the action, this home offers an ideal escape. Imagine unwinding on the expansive screened-in porch, taking in the peaceful views of calm waters, or dropping a crab pot to catch some of Maryland's renowned Blue Crabs.