Vacation rentals in Saint Leonard

4.93 out of 5 average rating, 203 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 --

4.91 out of 5 average rating, 32 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.

4.99 out of 5 average rating, 212 reviews

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

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, 347 reviews

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🥰

Guest suite in Mechanicsville

A small outdoor seating area features a round blue table surrounded by two gray plastic chairs. The setting is nestled among lush greenery, with trees providing a natural backdrop that enhances the tranquil environment.

5 out of 5 average rating, 16 reviews

Private Walkout In-Law Suite

Enjoy completely private walkout basement suite in home at end of country road. Has 1 bedroom, kitchen and bath. Enjoy views of local farms and horses. Home owners live on main floor and are available if needed. NO smoke/vape. Must be able to use stairs. Great location for contractors, travelers and interns working at PAX, Calvert Cliffs or St. Marys Hospital. Relax on back patio surrounded by tall trees. Easy access to all of Southern Marylands charms or drive into DC/VA for sightseeing.

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.

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!

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.

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.

4.99 out of 5 average rating, 302 reviews

Home in Lusby

Cove Point Beach Cabin

My place is close to shopping, restaurants and dining in Lusby and Solomons Island, the Chesapeake Bay, and family-friendly activities. You’ll love my place because of the comfy beds, the coziness, and the views. My place is good for couples, solo adventurers, business travelers, and families (with kids). No pets allowed.

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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 stars2 weeks 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.

4.87 out of 5 average rating, 53 reviews

Hickory House on the Chesapeake Bay!

HollyRating, 5 stars2 days ago

Beautiful, cozy place with a short walk to several lovely beaches! Theresa was a great host.

Sturdy wooden stairs lead to an elevated deck, featuring a natural wood finish. The railing is designed for safety, providing an open view of the surrounding area. Soft grass is visible at the base, complementing the home’s green exterior.

Apartment in Saint Leonard

5 out of 5 average rating, 4 reviews

The Loft at Flag Harbor

LisaRating, 5 stars3 weeks ago

Loved this location! So close to great beaches and close enough to drive quickly to local restaurants. Plus the food truck right outside was a plus! Definitely get the ice cream!

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, 206 reviews

Serenity Suite on Chesapeake Bay

KristaRating, 5 stars5 days ago

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 stars1 month 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.

The view showcases a serene outdoor space with lush green lawn leading to the beach. Two hammocks are suspended between trees, and a fire pit sits on the grassy area. In the background, the calm water of the bay and clear blue sky enhance the peaceful setting.