
Vacation rentals with beach access in St. Leonard
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Top-rated beach access rentals in St. Leonard
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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 --
4.91 out of 5 average rating, 269 reviews
Hot Tub Hideaway by Shark Tooth Shores
With views of the Chesapeake Bay, access to private beaches, a brand new hot tub, air hockey table, kayaks, and being just minutes away from hot spots like Calvert Cliffs and Solomon's Island the Hollow makes for the perfect vacation destination. Enjoy sunrise views through the treetops each morning on the expansive back deck, or use our eco-friendly wood burning stove for autumn and winter nights. Unlike many beach houses, this home is surrounded by trees making it serene. UPDATED PHOTOS SOON
4.85 out of 5 average rating, 101 reviews
Waterfront with sweeping bay view & private beach
Year-round private beach oasis on Chesapeake Bay! Perfect Fall & Winter Escape. An hour from DC beltway & world away. Recharge & relax to the sound of waves & sailboats. Spacious & fully renovated, with modern features, ample outdoor terraces. Enjoy long walks, nature spotting (bald eagles, rays, dolphins), shark tooth collecting. Kayaks provided! Short drive to Solomons Island, and local amenities: restaurants, bars, store, national parks & vineyards. No parties or events. Only relaxing.
4.97 out of 5 average rating, 113 reviews
Soul Oasis - home on the Chesapeake Bay
Listen to the waves of the Chesapeake Bay from the trex deck. There are 2 private community beaches in the neighborhood where you can find fossils and sharks teeth. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer around the house! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.
4.95 out of 5 average rating, 146 reviews
Cove Point Cottage with Chesapeake Bay views
Welcome to our beach house, just a block from the Cove Point Beach on the Chesapeake Bay. Start your beach day by grabbing the beach wagon from the shed, loading it up with beach chairs, towels, and your cooler. A short stroll takes you to the beach, where you can spend the day searching for shark teeth and shells or swimming in the bay's refreshing waters. After a day in the sun, rinse off in our outdoor shower. Our shady patio provides the perfect spot to relax and enjoy the evening breeze.
4.98 out of 5 average rating, 260 reviews
Its always a good day by the water!
Enjoy our private Loft apartment with exclusive beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home. You have a private entrance, so come and go as you please! Note: We are a peanut-free and smoke free property. RELAX in our chic, private loft just minutes from Chesapeake beaches and 10 minutes from Solomons Island & Calvert Cliffs. You will have private access to our amazing beach-- just a 5 minute drive away. Please let us know if you plan to use it!
5.0 out of 5 average rating, 427 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.
4.92 out of 5 average rating, 199 reviews
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, 253 reviews
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!
4.98 out of 5 average rating, 119 reviews
Historic Rousby Hall, Waterfront, Pool, Beach
Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).
4.99 out of 5 average rating, 178 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.
4.97 out of 5 average rating, 126 reviews
Waterfront Cottage ❤️ Private Beach, Dock & Kayaks
Welcome to Sunset View Cottage. A spacious and bright two-level waterfront home with a private dock and beach access in Leonardtown, MD. Enjoy swimming off the dock and beach in the Potomac River. Full western views across the widest part of the river make for unbelievable sunsets. Your ideal family vacation, couples getaway, or work-from-home retreat just 90 minutes outside DC. Visit us on IG @sunsetviewcottage
4.97 out of 5 average rating, 137 reviewsPopular amenities for St. Leonard beach access rentals
Apartment rentals with beach access

Spacious Beach House Top Floors - Walk Everywhere!
4.85 out of 5 average rating, 117 reviews
Historic St. Mary's City, MD
4.97 out of 5 average rating, 625 reviews
Romantic Wtrfnt Flat w Hot Tub@Chesapeake Paradise
4.91 out of 5 average rating, 625 reviews
Sail Away To - Beachfront Views & Private Balcony
4.94 out of 5 average rating, 101 reviews
Little Slice of Cambridge. 2 bedroom, pet friendly
4.91 out of 5 average rating, 158 reviews
King George Downtown Annapolis Getaway
4.85 out of 5 average rating, 129 reviews
The Loft at Flag Harbor
4.89 out of 5 average rating, 19 reviews
Coastal Hideaway near CalvertCliffs • Beach Access
4.93 out of 5 average rating, 15 reviewsHouse rentals with beach access

Spacious Lake House at the Chesapeake Bay
4.92 out of 5 average rating, 107 reviews
Iconic Chesapeake. Unparalleled Luxury.
5.0 out of 5 average rating, 217 reviews
SoMD Waffle House 1.5 acres of cozy coastal living
4.91 out of 5 average rating, 120 reviews
Waterfront Home on the Chesapeake Bay-Pvt Beach
4.95 out of 5 average rating, 189 reviews
Waterfront home, private dock
4.97 out of 5 average rating, 111 reviews
Waterview cottage on Chesapeake Bay
4.8 out of 5 average rating, 202 reviews
The River House: A private waterfront oasis…
4.94 out of 5 average rating, 100 reviews
Charming Historic 2 Bedrooms on the Chesapeake Bay
4.9 out of 5 average rating, 114 reviewsOther vacation rentals with beach access

Coastal Waterfront 1 Bedroom Cottage
5.0 out of 5 average rating, 226 reviews
Gettin to the point. ( Cove Point Beach)
4.98 out of 5 average rating, 301 reviews
“Cabana by the Bay”-tiny home on a pier!
4.96 out of 5 average rating, 742 reviews
Bayfront Walk-Out Beach Home | Sunrise & Fire Pit
4.99 out of 5 average rating, 113 reviews
Waterfront-View of Bay from your Bed
4.99 out of 5 average rating, 371 reviews
Waterfront Cottage on the Potomac River
4.99 out of 5 average rating, 218 reviews
Hickory House on the Chesapeake Bay!
4.91 out of 5 average rating, 97 reviews
Closest Home to Private Beach • Stunning Bay Views
5.0 out of 5 average rating, 26 reviewsDestinations to explore
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