Holiday houses in St. Leonard

4.92 out of 5 average rating, 267 reviews

The vintage A-frame home is nestled amongst trees, featuring a deck with a canopy in the foreground. A stone path leads to the entrance, where large windows allow for ample natural light. The surrounding landscape is adorned with greenery and decorative plants.

Cabin in Lusby

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 --

A spacious deck offers views of the waterfront and distant horizon. The serene blue waters of the Chesapeake Bay are visible, with gentle waves lapping against the shore. A railing lines the deck, providing safety and unobstructed sightlines to the beach.

4.92 out of 5 average rating, 37 reviews

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.

5.0 out of 5 average rating, 24 reviews

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.

4.89 out of 5 average rating, 19 reviews

Apartment in St. Leonard

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.

Guest suite in St. Leonard

A wooden pier extends over calm water, with posts on either side providing stability. The clear blue sky is marked by scattered clouds, while lush green trees and land form the background. A small ladder is visible at the edge of the pier, enhancing accessibility.

Exclusive Waterfront Hideaway in St. Leonard

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.

4.95 out of 5 average rating, 39 reviews

4.93 out of 5 average rating, 96 reviews

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.

A bright and open living space features large windows that provide views of the river. A long dining table is accompanied by upholstered chairs. A modern kitchen counter with stools is visible, along with a chandelier overhead and a cozy fireplace on one side.

4.97 out of 5 average rating, 105 reviews

Blue Pearl-Luxury estate with private dock/jacuzzi

The Blue Pearl is a luxurious river front estate with a private pier to catch crabs, fish and kayak. Soak in the outdoor jacuzzi and enjoy the river life. Three bedrooms with three full bath en-suites and over 2800 square feet of luxury accommodations await you. Office has Queen sleeper sofa. Pull up to your private boat dock, catch blue crabs with the provided traps, toast s’mores in the firepit while sitting in your Adirondack chairs. Enjoy two decks to view the sunrises and sunsets.

The exterior of the house showcases multiple large windows that invite natural light, with a spacious porch area featuring white outdoor chairs. Colorful flower planters enhance the surroundings, providing a serene setting among greenery.

4.92 out of 5 average rating, 199 reviews

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.

A spacious deck features a picnic table and several adirondack chairs, providing ample seating for outdoor relaxation. Lush greenery surrounds the area, with a distant view of the water visible beyond the railing. A grill is situated at the corner of the deck.

4.94 out of 5 average rating, 69 reviews

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.

Apartment in Port Republic

A red umbrella provides shade over a square table with a glass top, accompanied by two cushioned chairs. Lush green grass surrounds the seating area, framed by tall trees and distant views of the water, creating a serene outdoor space.

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.

4.96 out of 5 average rating, 250 reviews

4.98 out of 5 average rating, 117 reviews

Guest suite in Lusby

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!

The exterior of a spacious six-bedroom home is showcased, featuring a symmetrical façade with a blend of brick and siding. Large black-framed windows reflect a clear blue sky and white clouds, enhancing the inviting appearance of the property.