Vacation rentals with a patio in Saint Leonard

4.93 out of 5 average rating, 208 reviews

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 --

5 out of 5 average rating, 173 reviews

Home in Shady Side

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5 Star retreat for those who value tranquility over spectacle. Set along the Chesapeake, it offers front-row seats to breathtaking sunsets—where golden light dances across the water. Inside, Nordic-inspired design meets quiet luxury, featuring award-winning mattresses and bedding that promise restorative sleep. Here, time slows, and luxury isn’t just something you see—it’s something you feel. We invite you to read the reviews of so many happy guests.

4.98 out of 5 average rating, 45 reviews

Luxury Family 5BR: Beach, GameRm, Arcade, MovieRm

• Sleeps 14: 3 King Beds, 1 Queen Bed, & 2 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 w/ life jackets Tucked into nature, Helm Haven has been called “a perfect getaway for families” & “a dream for kids and adults alike.” Our guest reviews say it best—luxury and fun in one!

5 out of 5 average rating, 120 reviews

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.

Superhost

4.86 out of 5 average rating, 50 reviews

Waterfront house with private beach and pier

Known for its peaceful, uncrowded anchorages and stunning natural surroundings, our property offers the perfect blend of relaxation and adventure. Catch fresh fish and crabs for dinner from our private pier, explore the river by kayak, or unwind in the backyard with a cozy fire pit and outdoor games. Step inside to enjoy a movie night with Disney+, or gather around the fireplace for family fun. Whether it’s summer sunshine or winter coziness, our estate is a year-round getaway.

4.96 out of 5 average rating, 145 reviews

Home in Lusby

Coastal Oasis On The Chesapeake, King Bd sleeps 12

Coastal Oasis On The Chesapeake is where you come to: RELAX, DECOMPRESS and RE-CHARGE! You'll experience all the tranquility & majestic beauty of PEACEFUL living on the Chesapeake Bay. You'll awaken to breathtaking & alluring sunrises while also being surrounded by nature's wooded bliss of starry nights. Located 4 miles from Solomon's Island. Contact host for pre-approval of pets, pet fee applies. Unregistered: guests/pets & smoking including marijuana will incur fines!

5 out of 5 average rating, 112 reviews

Home in Dameron

Peace Point - Waterfront, Secluded, Home w/hot tub

Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

4.94 out of 5 average rating, 72 reviews

Cottage on the Bay

Relax with the whole family at this peaceful place to stay. This beach cottage is in walking distance or a short drive to three private beaches in our community. We provide a parking pass to two of the beaches (one has no parking available). Please click each photo for a description. Wanna fish??? Ask Joey about Fish Taxi! 1 hour from DC/Joint Base Andrews /Annapolis. 45 minutes from Waldorf. 15 minutes from Solomons Island and Prince Frederick

4.96 out of 5 average rating, 100 reviews

Cottage in Leonardtown

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

Guest suite in Chesapeake Beach

4.96 out of 5 average rating, 116 reviews

Nice Guest Suite at Chesapeake Bay

Take it easy at this unique and tranquil getaway. Come and relax in our modern & comfortable guest suite to enjoy a small-town quiet setting with amazing Chesapeake Bay views. A short drive from Washington DC (45 min), Annapolis (30 Min), or Baltimore (1 hr). Groceries, boardwalks, restaurants are all within walking distance. Enjoy cable TV, high-speed Internet, and strong wifi through Xfinity.

4.98 out of 5 average rating, 110 reviews

Home in Montross

Waterfront | Kayaks+Beach+Pool | Gameroom+Firepit

☀️ Waterfront 🏊‍♀️ Community pool 👨‍🍳 Gas griddle 🛶 Kayaks/Paddleboard 🔥 Fire pit ⛱️ 3 Community Beaches 🎯 Gameroom (ping pong, arcade, & more!) ⚡️ EV Outlet 🐶 Dogs OK Relax - Kayak - Paddleboard - Hike - Fish - Swim - Beach & more at the Riverside Retreat in Montross, VA! Book today or ❤️ us for next time