Vacation rentals in Saint Leonard

4.93 out of 5 average rating, 202 reviews

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

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 --

4.98 out of 5 average rating, 347 reviews

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

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🥰

5 out of 5 average rating, 117 reviews

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

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.

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.

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.

The exterior of the home is framed by lush greenery, with a large deck featuring multiple seating areas. A gravel driveway leads to the garage, and outdoor games are set up in the yard, inviting play. The warm hues of a sunset enhance the inviting atmosphere.

4.98 out of 5 average rating, 41 reviews

Luxury 5BR: Beach, GameRm, Arcade, Theater

• Sleeps 14: 3 King Beds, 1 Queen Bed, & two bunk beds • Game Room: arcade games, air hockey, climbing wall, ship’s wheel, ping pong • Movie room: 100” screen w popcorn machine! • Enjoy stunning Bay views and sunrises from our spacious living & dining areas • Private community beach - 3 min walk • 3 Kayaks Nestled in nature, Helm Haven is “a perfect getaway for families” & “a dream for kids and adults alike.” Enjoy everything you need for a luxurious and fun escape!

4.97 out of 5 average rating, 235 reviews

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

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.

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.

4.9 out of 5 average rating, 266 reviews

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

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.

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!

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.

4.96 out of 5 average rating, 141 reviews

A hot tub is situated outdoors, surrounded by a gravel area. Water is seen bubbling inside, indicating a relaxing atmosphere. The hot tub is designed with a round shape and features built-in seating. Natural light creates soft reflections on the water's surface.

Cottage in Saint Leonard

Block to Private Beach, Screened deck, Hot Tub

Relax at this renovated cottage with views of the Chesapeake Bay! Features large screened deck, hot tub, around corner from private community beach where you can find fossils and shark teeth! (4 min drive to larger community beach.) (No cleaning fee and multi night discounts! Message us for monthly rates.)

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Other great vacation rentals in Saint Leonard

Apartment in Prince Frederick

The bathroom features a shower-tub combination, a light-colored vanity with a mirror above, and organized shelving. The soft, beige towel hanging beside the sink adds a neutral touch. A window offers natural light, while a plush bath mat is placed near the tub.

4.78 out of 5 average rating, 23 reviews

Pop's Place

NoahRating, 5 stars1 week ago

Had a great stay at Marsha’s places 0 complaints. Very friendly she made sure I had everything I needed and made sure to check up on me. Most friendly and caring host I have experienced on airbnb. Would stay again and recommend for others.

4.86 out of 5 average rating, 51 reviews

Hickory House on the Chesapeake Bay!

DamonRating, 5 stars2 weeks ago

Great neighborhood. Close to the water.

Superhost

A spacious bedroom is highlighted by large windows, providing views of the Chesapeake Bay. Light-colored walls complement the wooden floor, while a patterned area rug sits beneath a stylish bed. Soft curtains frame the windows, enhancing the bright and airy ambiance.

Home in Prince Frederick

4.83 out of 5 average rating, 6 reviews

Chesapeake Escape

MicheleRating, 5 stars3 days ago

Diana’s place was perfect for our family. The house had many of the items we would have had to bring from home. You can tell she wanted people to feel at home and be comfortable. My grandbabies loved the books. The neighbors were friendly. The neighborhood was nice to get a quick walk in before the day started.

An open living space is highlighted by a combined dining and lounge area. A rectangular table with gray stools sits in the foreground, while a comfortable sectional sofa and a wall-mounted television are positioned across from large windows with white blinds.

Apartment in Saint Leonard

5 out of 5 average rating, 3 reviews

The Loft at Flag Harbor

KatieRating, 5 stars3 weeks ago

Great and convenient stay for our beach weekend! The apartment was comfortable and clean, with a beach within walking distance. Also easy drives to antiques stores and Flag Pond for shark tooth hunting. Hosts were great and let us stay longer at check out due to a surprise flat tire!

Apartment in Port Republic

A wooden swinging bench is suspended under a wooden structure, surrounded by lush green grass and mature trees. Views of the bay can be seen in the background, providing a serene setting for relaxation.

4.97 out of 5 average rating, 205 reviews

Serenity Suite on Chesapeake Bay

KristaRating, 5 starstoday

This is our second time staying at this cozy and tranquil retreat—and it won’t be our last. We first came here six months ago for a quiet getaway from the kids, and we liked it so much we knew we’d be back. This time was just as wonderful. The place is spotless, peaceful, and incredibly relaxing. The view of the bay is absolutely stunning—calm, quiet, and the perfect backdrop for unwinding. The hosts are warm and welcoming, and the space has everything you need for a comfortable and refreshing stay. If you’re looking for a serene escape with beautiful scenery and thoughtful touches, this is the place. We’re already planning our next visit.

4.72 out of 5 average rating, 211 reviews

A classic lighthouse stands on rugged rocks, illuminated by the warm glow of the setting sun. The surrounding landscape features scattered trees and distant islands, while the serene waters extend beyond the rocky shore, reflecting the calming colors of twilight.

Apartment in Lusby

Nice view self-contained Apart.

MargaretRating, 5 stars4 weeks ago

I really enjoy staying here at nice view. very peaceful and close to work. has everything I need and very comfortable bed. always responsive when I had a question. would definitely stay here again.

4.9 out of 5 average rating, 129 reviews

Home in Broomes Island

Gorgeous Waterfront Home!

RichardRating, 5 stars5 months ago

Another lovely stay. Perfect for visiting relatives in the area. Thank-you Tom and Julie.