Holiday rentals in Saint Leonard

4.93 out of 5 average rating, 205 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 --

4.99 out of 5 average rating, 212 reviews

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.

4.9 out of 5 average rating, 130 reviews

Perfect Bay and Beach Getaway one hour from DC!

Our waterfront home with sweeping views of the Chesapeake Bay is close to beaches, the Flag Harbor Marina, Solomon's Island, Flag Pond Nature Preserve and Calvert Cliffs State Park. You’ll love the spectacular sunrises/sunsets over the Bay, diving ospreys and eagles, and exploring the bay by kayak, canoe, or paddle board. Our house is great for families (with kids), groups, and well-mannered dogs. New in 2023: we will be replaced the upstairs HVAC system, baby proofing, and fall 2023 paint

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🥰

4.95 out of 5 average rating, 41 reviews

J.K.'s by the Bay

Escape to the "Chesapeake Bay - Land of Pleasant Living" This beautifully restored 1950's bayside beach cottage just underwent a major transformation in 2023. Enjoy stunning views of the bay and a private community beach. Discover the history of Southern Maryland, Calvert Cliffs, Flag Ponds State Park and Point Lookout. Famous for fossil hunting. Nature lovers paradise. Kayaking, biking and hiking. Perfect throwback vacation. Come savor some seafood, unwind and discover a gentler time.

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, 43 reviews

Luxury Family 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, 112 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, 268 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, 6 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, 118 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.

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Other great holiday rentals in Saint Leonard

5 out of 5 average rating, 56 reviews

Guest suite in Lusby

Welcome to Journey's End Hideaway!

Nicole JenniferRating, 5 stars1 week ago

Our stay was peaceful and relaxing. we loved sitting on the dock watching the birds and fish every morning and evening. Sunset is gorgeous.

4.87 out of 5 average rating, 54 reviews

Hickory House on the Chesapeake Bay!

KendraRating, 5 stars2 days ago

beautiful home and such a great location. close to everything. absolutely would come back and stay longer. very clean when we arrived and had everything we needed and more.

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 stars4 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, 207 reviews

Flat in Port Republic

Serenity Suite on Chesapeake Bay

RadiaRating, 5 stars1 week ago

We loved our stay! Lori’s backyard is so beautiful and full of nature. We spent a lot of time sitting in the yard taking in the view! Her Airbnb is awesome, very clean, super comfortable. Thanks for a great stay!

4.72 out of 5 average rating, 211 reviews

Flat 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, 130 reviews

Home in Broomes Island

Gorgeous Waterfront Home!

AtifaRating, 5 stars2 days ago

We got there and instantly felt at peace! The beautiful sounds of nature and the water, having dinner under the willow tree and there is a playful bunny that seems to enjoy being around the house as well which we thought was adorable. The rooms were clean and the AC was good, the kitchen was well prepared and the bathroom was roomy! Also very nice area for a photoshoot which we utilized well :) the owner gave us many suggestions of places to go and things to do as well. Would definitely come back!