Vacation rentals in Saint Leonard

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Top-rated vacation rentals in Saint Leonard

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Guest favorite

An outdoor fire pit is surrounded by several black adirondack chairs, creating a cozy gathering space. The scene is set against a backdrop of lush trees and St. Leonard's Creek, with dusk settling in and a soft blue hue filling the sky.

Cabin in Lusby

4.93 out of 5 average rating, 202 reviews

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 --

Top guest favorite

A sandy beach extends along the shore, meeting the calm waters under a pastel sky. A lighthouse stands tall in the distance, accompanied by a house with a red roof. The shoreline appears tranquil, with gentle waves lapping at the sand.

Home in Lusby

4.99 out of 5 average rating, 211 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.

Superhost

A blue kayak is propped against a tree on the riverbank, alongside a paddle and a red life jacket. The water is visible through the surrounding foliage, highlighting a serene natural setting.

Bungalow in Lusby

4.77 out of 5 average rating, 47 reviews

Quiet cottage on wooded property

Secluded location for those who like nature and view of water through the trees. Walk down the hill to the creek to launch a boat, fish or watch the spectacular sunsets. The cottage has a sleeping loft with twin beds and a sofa bed in main living area. Furnished and equipped for short to longer stays close to Cove Point, Calvert Cliffs and across the river from PAX Naval Air station. Minimum stay is 2 nights. Just updated with cable tv and wifi. New flooring. Deep cleaned between guests.

Top guest favorite

A cozy bedroom features a wooden bed adorned with soft linens and decorative pillows. Warm string lights drape along the sloped ceiling, creating a gentle glow. Framed artwork and bedside lamps add character to the space, while the walls exhibit a calming blue hue.

Guest suite in Lusby

4.98 out of 5 average rating, 347 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is Solomon’s island. This is a safe space for all🥰

Top guest favorite

A bright sun porch is highlighted by large windows offering views of the waterfront. Comfortable seating is arranged around a central coffee table, while decorative cushions add a touch of color. Natural light enhances the serene ambiance, creating an inviting space for relaxation.

Home in Leonardtown

5 out of 5 average rating, 117 reviews

White Point Cottage -- Quiet Waterfront Getaway

Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. More on IG @whitepointcottage, and be sure to visit our sister property, Water's Edge Cottage.

Guest favorite

A bench is positioned along the shoreline, offering views of the Chesapeake Bay. Waves gently lap against the rocky edge, while sunlight reflects off the water. Grass and scattered stones create a natural transition to the beach area.

Home in Saint Leonard

4.92 out of 5 average rating, 178 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.

Top guest favorite

A welcoming cottage exterior features a covered porch with seating, light fixtures, and colorful plantings. A walkway made of stone leads to the entrance, and the surrounding landscape is highlighted by well-maintained grass and nearby neighboring homes.

Cottage in California

4.97 out of 5 average rating, 235 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has an open floor plan that allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum featuring live concerts by top name bands.

Top guest favorite

Guesthouse in Saint Leonard

4.96 out of 5 average rating, 111 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.

Guest favorite

A wooden dock features railings and lighting, leading down to calm waters reflecting the twilight sky. Silhouetted trees frame the serene scene, emphasizing the tranquility of the natural surroundings. The path is well-defined, providing clear access to the waterfront.

Cabin in Lusby

4.9 out of 5 average rating, 266 reviews

Peaceful Waterfront Retreat on The Bay

Escape to a serene waterside cabin with a private dock on quiet St. Leonard Creek, just an hour from Washington, DC. This rustic studio offers a cozy retreat for solo travelers, couples, or small families looking for peace and relaxation. Whether you're here to unwind, work remotely, or explore the outdoors, you'll find plenty to enjoy—including two kayaks, two canoes, and stunning waterfront views.

Top guest favorite

Farm stay in Port Republic

5 out of 5 average rating, 106 reviews

Maple Hollow Farm - A Little Piece of Heaven

Enjoy the modern farmhouse charm of this lovely apartment here at Maple Hollow Farm! This space includes all new furnishings, appliances, amenities and unique, stylish decor. You will enjoy a spectacular view off the attached deck that typically includes the horses grazing in the pastures and an amazing sunset! It's a fabulous location for your next getaway or even stay-cation!

Guest favorite

Large glass doors lead to a wooden deck, revealing a serene outdoor seating area with multiple chairs. Sunlight filters through trees in the background, and a cozy indoor seating area is visible, featuring a coffee table with books and a decorative bowl.

Home in Saint Leonard

5 out of 5 average rating, 5 reviews

Waterfront Home, Spectacular View & Private Beach!

Escape to this beautiful beach-front gem with breathtaking views of the water. This stunning home offers the ideal getaway for families and friends alike. Experience the beauty of waterfront living and create unforgettable memories at this stunning escape. Book your stay today. Inquire about our off-season discounted rates for long-term stays.

Superhost

An open floor plan is revealed, featuring a spacious kitchen island with blue cabinetry and a granite countertop. A large dining area is visible in the background, complemented by natural light from nearby windows, while a staircase leads to the upper level.

Cottage in Saint Leonard

4.87 out of 5 average rating, 116 reviews

Spacious Beachfront Retreat w/Dock

Relax with the whole family at this peaceful place to stay. This charming home features 5 bedrooms and 3 full bathrooms. All bedrooms have a waterfront view. Enjoy watersports - kayaking, fishing, paddle boarding; or relax on the beach by a fire and enjoy the sunset. Bring your jet skis or fishing boat, the marina is 5 miles away.