Holiday rentals in Saint Leonard

4.93 out of 5 average rating, 204 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 --

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

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.

5 out of 5 average rating, 117 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.

4.92 out of 5 average rating, 179 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.

4.98 out of 5 average rating, 42 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!

Guest house 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

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

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 holiday rentals in Saint Leonard

4.78 out of 5 average rating, 23 reviews

Flat in Prince Frederick

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 stars3 days ago

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

5 out of 5 average rating, 15 reviews

Cottage in Lusby

Cozy Cottage close to Beaches & Solomon’s Island

LindaRating, 5 stars1 month ago

Emilio and Wanda’s home was absolutely lovely. They thought of everything to make our stay so enjoyable. Would recommend to anyone wanting a relaxing stay. So very close to Solomon’s Island. Thank you Emilio and Wanda!

Flat 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!

4.97 out of 5 average rating, 206 reviews

Flat in Port Republic

Serenity Suite on Chesapeake Bay

KristaRating, 5 stars1 week 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.

5 out of 5 average rating, 72 reviews

Houseboat in Solomons

Island Shanty

SherriRating, 5 stars3 weeks ago

Clean, quiet, and convenient. Would stay 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.