Vacation rentals in St. Leonard

Closest Home to Private Beach • Stunning Bay Views

Wake up to unobstructed Chesapeake Bay views and walk to the sand in seconds. This is the closest home to Long Beach's private beach access—there are no homes between you and the water. Relax on the expansive front deck overlooking the Bay, enjoy the screened porch, fire pit, grill, kayaks, and games. Spend your days hunting for shark teeth, fishing, kayaking at sunrise, or exploring Calvert Cliffs, Flag Ponds, and Solomons Island. A peaceful beachside escape designed for unforgettable memories.

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Escape to the Bay~Waterfront

Waterfront with private beach! The perfect house for a family getaway, friends gathering or special occasion. Vacationers have visited here since the early 1940’s. Like them, you can enjoy boating, fishing, crabbing, fossil hunting, and swimming. This house is a three story waterfront house in Long Beach, Maryland right on the Chesapeake Bay. It sits in a quiet, friendly neighborhood in a private beach community. Nearby is Flag Ponds Nature Park, Calvert Cliffs State Park and other attractions.

Waterfront! The River's Roost on the Patuxent!

Situated right on the Patuxent River and offering endless opportunities for fun, this house is the most idyllic place to escape on your next coastal Maryland getaway. Complete with 3 bedrooms, 3 full bathrooms, 1 half bathroom, and 3,000 square feet of updated and stylish interior, this vacation rental is brimming with everything you need on your St. Leonard stay. Don't forget to take advantage of the outdoor spaces like the 2 wraparound decks, the boat dock, and the peaceful backyard tiki bar!

The Loft at Flag Harbor

The perfect coastal getaway just moments from the water in beautiful St Leonard, MD. This clean, spacious, & thoughtfully designed second story loft offers the ideal balance of convenience & relaxation perfect for families, couples, or small groups looking to unwind near the beach while still being close to local attractions. Come for slow mornings with coffee, beach days, or peaceful evenings on the deck, this space gives you that effortless “vacation mode” feeling from the moment you arrive.

Ocean Break

Your peaceful retreat by the beach. This cozy, private space is located 40 steps up, giving you a quiet, elevated setting where you can pause, breathe, and truly unwind. Surrounded by a peaceful coastal atmosphere, it’s a welcoming place for rest, reflection, or simply a relaxing getaway. While it feels like a hidden escape, you’re still just 10 minutes from the shops and restaurants in Prince Frederick and only 20 minutes from the lively waterfront of Solomons Island and the iconic Tiki Bar.

Exclusive Waterfront Getaway

Nice to unwind, waterfront views with separate private entrance, private parking and water access on pier. Use our kayaks or paddleboard or crab , fish on our private pier at this unique and tranquil getaway. [ no fishing license required on private pier] . Fire pit near water for your cookouts[firewood provided]. If you choose to come by boat, there is plenty of room to tie up. Combined living room/bedroom sleeps up to 4. Quiet and peaceful overlooks beautiful St. Leonard Creek.

Hickory House on the Chesapeake Bay!

Welcome to Hickory House on the Bay! Charming 2 bedroom, 1 bath cottage overlooking the Bay within walking distance of two community beaches as well as a beach car pass. Relax, enjoy the water view, sounds and breezes. Explore this charming and tranquil community, Long Beach by the Bay. Enjoy all that Southern Maryland offers from this centrally located home - Hiking in Calvert Cliffs, kayaking, fishing, boating, exploring local vineyards, dinner in Solomon’s, visiting Historic St Mary’s.

Cozy Cottage on the Chesapeake Bay

Tranquility supreme. Sit on the terrace and gaze at the Chesapeake Bay. Sandy beach -- just 50 steps from front door; quiet residential area; nearby antiquing & fishing; Only 75 min. from DC. Finish your book or just replenish your spirit. Enjoy. Oh, one more thing — looking for the perfect place for a retreat for your small DC team? Strategic planning will be even more creative and enjoyable when you have the Chesapeake Bay as your muse. Note: This property is for non-smokers.

Block to beach! Relax, enjoy views & game room.

Great escape - Beautiful views Chesapeake Bay with community beach only a block away! 3 Bedroom plus bunk area. Large deck with grill overlooking the bay! Huge rec room upstairs with Bunk Bed, Air Hockey, Shuffleboard, and Foosball. Master Bath with large soaking tub. Close to Cove Point, Calvert Cliffs, Annapolis, Solomons Island & PAX Naval Base. Great place for those Calvert Cliff Nuclear Plant! No Smoking. Space upper 2 levels. $150 pet/dog. No shedders please.

Serenity Suite on Chesapeake Bay

Come enjoy our waterfront home on the scenic Calvert Cliffs. Take in beautiful Bay views in Adirondack chairs with stunning vistas. Photograph wildlife. Comfortable ½ mile walk to private community bay shoreline. Have breakfast in the yard while enjoying the sunrise. Stroll the community shoreline and explore fossil hunting, hike at nearby trails. No pets are allowed because I have a severe allergic reaction to pet hair and dander. Thanks for your understanding.

Waterfront on St. Leonard Creek at Fort Hill

Waterfront home on St. Leonard Creek w/ private pier for fishing and relaxing, PLUS a small beach area. Close to Solomons, fossil hunting at Calvert Cliffs, the Calvert Marine Museum (and their concerts), and other area attractions. Forget stairs! Our elevator directly connects the parking area to your private floor! Fort Hill is a uniquely quiet and private space with wide-open views of the outdoors. 4 kayaks are included FREE for you to enjoy!