Airbnb your place

Holiday houses in Leonardtown

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Leonardtown

  • Total holiday rentals

    Explore 10 holiday rentals in Leonardtown

  • Nightly prices starting at

    Leonardtown holiday rentals start at $68 NZD per night before taxes and fees

  • Verified guest reviews

    Over 670 verified reviews to help you choose

  • Wi-Fi availability

    10 of Leonardtown holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Leonardtown rentals

  • 4.9 Average rating

    Leonardtown stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated holiday rentals in Leonardtown

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
Top Guest favourite
A spacious wooden deck is showcased, extending from the house and featuring several outdoor chairs arranged around a table. The sun sets in the background, casting a warm glow over the grassy yard and the nearby water, enhancing the serene ambiance.
Home in Leonardtown
4.94 out of 5 average rating, 100 reviews

The River House: A private waterfront oasis…

Cozy up by a roaring fire with your partner and relish the winter chill! This private waterfront retreat offers panoramic water views of the Potomac River and sits at the mouth of Breton Bay. At the end of the road and occupying two acres, the property is a private oasis of year-round natural beauty. You’ll have 650’ of waterfront to yourself to lounge at the waterside tiki-bar deck, on the screened-in porch, on the house deck, in the yard or on the hammock. Kayak, canoe, chill however you like!

FamilyLocationAccuracy

Top Guest favourite
An aerial view captures the waterfront home surrounded by lush greenery with a private dock visible by the water. The neatly maintained property features landscaped lawns and nearby homes, illustrating a serene setting alongside Neale Sound.
Home in Cobb Island
4.99 out of 5 average rating, 140 reviews

Waterfront 4-BR home w/ hot tub & charging station

Immaculately maintained 4-bedroom waterfront home + home gym on Cobb Island with water views from every window! Four beach cruiser bikes & private dock w/ 4 kayaks, to enjoy the peaceful Neale Sound. Hot tub + private deck off of the kitchen. Wall of windows inside the home, flooded w/ natural sunlight. Views of the sound & the river side of the island. 3 BR are large (2 King beds/1 Queen), w/ their own BA (1 BR w/ BA is on 1st floor, no stairs). Smart TV's in 3 BR's. Great entertaining space!

FamilyValueAmenities

Top Guest favourite
A wooden dock extends into calm waters, showcasing a boat moored at the end. The serene surface reflects the pastel colors of the sky during dusk. Wooden posts line the edges of the dock, enhancing the tranquil setting.
Home in Newburg
4.91 out of 5 average rating, 128 reviews

The River House, a Wicomico Beach Retreat

Located right on the water of the Wicomico River with a private sandy beach, The River House will become your favorite retreat! This 5 bdrm, 3 bath fully stocked home has all the convenience of modern construction (including wifi) but maintains the vintage charm of the original property. The acre+ plot is very private with spectacular forest & water views. Fun can be found in every direction and for all ages! It has two bottom floor bed/bath combos, plus a fabulous sleeping loft for the kids!

LocationFamilyCheck-in

Top Guest favourite
A cozy living area is shown, featuring a gray sofa with cushions and two soft ottomans. A wooden desk with a chair is positioned to the left, while a bright window allows natural light to fill the space. A small plant and framed artwork add a touch of decor.
Apartment in Leonardtown
4.96 out of 5 average rating, 113 reviews

Retreat at Fenwick

This cozy one bedroom apartment is the perfect place to unwind & relax. Located in the heart of downtown Leonardtown, the Retreat at Fenwick is steps away from many delicious dining opportunities, unique and fun shopping at local boutiques, and entertainment experiences. It includes free wifi, a full kitchen & complimentary coffee bar, a charming eat-in dining space, queen size bed, full size pull out sofa bed, a cozy electric fireplace, workspace, and twin bunkbeds that are great for kids!

FamilyLocationSleep quality

Top Guest favourite
The exterior of a two-story house is showcased, featuring light blue siding and white railings. A grassy area is visible in front, with four gray Adirondack chairs arranged around a circular fire pit on a stone patio. The sun casts a warm glow over the scene.
Home in Solomons
5.0 out of 5 average rating, 139 reviews

The Little House on Back Creek

Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

LocationFamilyBiking

Top Guest favourite
Cottage in Leonardtown
4.96 out of 5 average rating, 275 reviews

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

FamilyLocationWalkability

Top Guest favourite
Two adirondack chairs and a small table are positioned on a grassy area overlooking Breton Bay. A vibrant sunset casts warm colors across the sky, reflecting on the calm water. The pier is visible in the distance, enhancing the serene scenery.
Apartment in Leonardtown
4.98 out of 5 average rating, 150 reviews

Stunning Sunsets on Breton Bay, Seaside apartment

Charming efficiency apartment decorated with a coastal theme overlooks Breton Bay. Use of pier for hanging out... or crabbing and fishing. Apartment is in the second floor of detached garage on the premises of a private home. Beautiful serene surroundings 5 min. from downtown Leonardtown with shopping, restaurants and events. Area offers historical sites, wonderful parks, a large Mennonite and Amish community, great restaurants and friendly people! 25 minutes from Solomons Island.

ValueLocationParks

Top Guest favourite
Home in Cobb Island
4.97 out of 5 average rating, 102 reviews

*Solitude At Sunset* A Waterfront Cottage Retreat.

YOUR WATERFRONT OASIS AWAITS! If you are looking for a true getaway, look no further. Tucked away on a small, peaceful island, this hidden gem is uniquely surrounded by 3 bodies of water: The Potomac River, the Wicomico River, and Neale Sound. This quiet island oasis offers the perfect place to step away from the busy world! This cottage is incredibly special to us. For four generations, it has been a sanctuary for our family-filled with love, laughter, and countless memories.

FamilyLocationBeach

Top Guest favourite
An exterior view of the home showcases a light grey facade with a gentle slope roof surrounded by trees. A gravel driveway leads to the entrance, while a calm waterway with a boat dock is visible in the background.
Home in Hollywood
4.99 out of 5 average rating, 107 reviews

Waterfront Home: Osprey Getaway

Welcome to The Osprey Getaway! This spacious home is the perfect destination for families seeking a relaxing retreat. Our home is not far from Solomon’s Island, Patuxent River Naval Air Station, St. Mary’s College of Maryland, and historic Leonardtown. Here you'll find an open floor plan and plenty of space to unwind and take in your surroundings. Enjoy the peace and quiet of Cuckold Creek and the beauty of our newly renovated home. We can't wait to share our home with you!

LocationValueComfort

Top Guest favourite
The exterior of a two-story duplex is featured, showcasing a light brown facade with white trim. A peach-colored front door is visible, adorned with a decorative lantern. Several windows are framed by black shutters, and greenery lines the pathway leading to the entrance.
Townhouse in Leonardtown
4.99 out of 5 average rating, 126 reviews

Charming Duplex in the heart of Leonardtown

This bright, stylish duplex is the perfect base to explore St Mary’s county. Nestled in downtown Leonardtown , this contemporary living space has everything to make you feel at home – WiFi, Netflix, washer and dryer, queen size beds in 2 of the 3 bedrooms, two twin beds in the 3rd. Kitchen is well equipped with just about everything you might need including basic spices, sugar and cooking oil. Spend your evenings relaxing on the back deck under the soft lighting.

FamilyValueNearby

Top Guest favourite
A spacious open-concept living area features large windows offering unobstructed views of the water and sunset. A comfortable sectional sofa is positioned near the windows, with a dining table visible in the background. Natural light fills the space, enhancing the tranquil setting.
Home in Leonardtown
4.99 out of 5 average rating, 139 reviews

Water's Edge Cottage | Luxury Retreat

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”).

ValueFamilySleep quality

Top Guest favourite
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
4.97 out of 5 average rating, 285 reviews

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.

LocationValueOutdoor spaces

Popular amenities for Leonardtown holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Stay near Leonardtown's top sights

Port of Leonardtown Winery

44 locals recommend

Leonardtown Wharf

43 locals recommend

Olde Town Pub

32 locals recommend

Other great holiday rentals in Leonardtown

Top Guest favourite
A view from the property shows a grassy area leading to the water. A screened porch is visible, providing a tranquil space. The river reflects the blue sky and fluffy clouds, with trees lining the opposite bank. A wooden dock extends into the water.
Guesthouse in Bushwood
4.94 out of 5 average rating, 186 reviews

Little House by the water

LocationFamilyWalkability

Guest favourite
Home in Leonardtown
5.0 out of 5 average rating, 8 reviews

The Primary House

FamilyLocationAccuracy

Guest favourite
A lush green lawn extends towards Breton Bay, bordered by trees and flowering plants. The calm water reflects the sky, with a red gazebo visible in the distance. Gentle hills create a serene backdrop, inviting relaxation and outdoor activities.
Home in Leonardtown
4.93 out of 5 average rating, 46 reviews

Abells Wharf Cottage - Natural Splendor Getaway

FamilyLocationHeating

Guest favourite
Home in Leonardtown
4.9 out of 5 average rating, 29 reviews

Anne & Fred's Leonardtown Home W/ Arcade room!

FamilyLocationComfort

Top Guest favourite
A peaceful waterfront scene is depicted, featuring chairs arranged on a grassy area. A picnic table and a flagpole stand nearby, while the sun reflects on the calm water. A private pier extends into the river, creating a serene atmosphere.
Home in Leonardtown
4.95 out of 5 average rating, 40 reviews

Potomac Fishing & Crab Paradise at Toney's Landing

FamilyLocationOutdoor spaces

Guest favourite
Home in Leonardtown
4.91 out of 5 average rating, 35 reviews

Waterfront Retreat | Sunset Views (Pet friendly)

FamilyValueBeach

Guest favourite
A stone patio is set with colorful adirondack chairs surrounding a fire pit, under the shade of large trees. A gazebo is visible in the background, and the calm water of the bay stretches out beyond the green space.
Home in Leonardtown
4.77 out of 5 average rating, 44 reviews

Waterfront Retreat, Your Home Away from Home

LocationValueAir conditioning

Superhost
Home in Leonardtown
4.8 out of 5 average rating, 15 reviews

Hidden Harbor House

FamilyLocationIndoor spaces

Frequently Asked Questions

  • What are the best places to stay in Leonardtown?

    Staying near the historic town square places you close to cafés, galleries, and community events. Waterfront neighborhoods around the wharf provide scenic views and easy access to outdoor activities.

  • What are the best things to do in Leonardtown with kids?

    Kids can enjoy the waterfront playgrounds at Leonardtown Wharf Park, interactive exhibits in small museums, and seasonal outdoor movies or festivals. Paddle sports and nature walks are also popular with families.

  • What are some of the best things to do in Leonardtown?

    Explore art galleries, stroll the Leonardtown Wharf Park, and visit local museums for stories of the region’s past. Sampling wines at the local winery or catching a seasonal festival are also frequently suggested activities.

  • How is the weather in Leonardtown?

    Leonardtown has chilly winters, with January days near 29–45°F (-1–7°C), and warm, humid summers approaching 87°F (31°C) in July. Spring and fall are milder, with temperatures often between 47–75°F (8–24°C) and regular rainfall.

  • When is the best time to visit Leonardtown?

    Spring and fall are often recommended for mild weather, blooming gardens, and outdoor festivals. Summer draws visitors with long, warm days and community events, while winter is quieter and suited to those preferring a slower pace.

  • What are the best places to visit in Leonardtown?

    Frequently suggested spots include the Leonardtown Wharf Park, the Old Jail Museum, and galleries around the town square. The local winery provides opportunities to sample regional wines in a scenic setting.

  • What are some hiking trails in Leonardtown?

    Walking paths at Leonardtown Wharf Park offer waterfront views and bird watching. For longer hikes and forest trails, nearby state parks and nature reserves provide more choices just outside town.

  • What are some family activities we can do in Leonardtown?

    Families can explore playgrounds and walking paths at Leonardtown Wharf Park, and visit hands-on art centers or historic museums around the square. Paddling, picnicking, and community events often round out the calendar.

  • What are some of the best day trip ideas from Leonardtown?

    Explore nearby state parks for hiking and wildlife watching, or visit regional wineries and historic plantation sites, some of which include interpretation of the area’s complex history. The surrounding region is also known for peaceful waterways and scenic countryside.

  • Are there any pet friendly accommodations available in Leonardtown?

    Many vacation rentals in Leonardtown welcome pets, particularly in neighborhoods around the waterfront and central town area. Some parks and outdoor spaces also allow leashed pets, so checking individual listings for details is helpful.

  • What are some local tips for visiting Leonardtown?

    Check out the town’s public art displays and consider visiting during market days for the freshest local produce. Early mornings are quieter for walking along the wharf or town square, and many guests enjoy sampling wines at nearby vineyards.

  • What is Leonardtown known for?

    Leonardtown is known for its historic courthouse square, waterfront park, and vibrant local arts scene. The town frequently hosts community events, culinary festivals, and showcases its Chesapeake Bay heritage.

  • What are the best hidden gems to explore in Leonardtown?

    Explore the Leonardtown Wharf Park for peaceful waterfront views and public art. The town’s galleries and historic courthouse square also provide a glimpse into local history and creativity. Little shops and tucked-away cafés offer quieter experiences around the central square.

  • What are the best foods to try in Leonardtown?

    Enjoy Chesapeake-inspired dishes such as crab cakes, oysters, and seasonal seafood. Local bakeries and creameries are also known for homemade ice cream and pies, reflecting regional culinary traditions.

  • What should I bring for a trip to Leonardtown?

    Pack comfortable walking shoes for exploring historic streets, a light jacket for cooler evenings, and sunscreen for time outdoors. Bringing layers can help accommodate changing temperatures, especially from spring through fall.

  • What is the nightlife in Leonardtown like?

    Leonardtown’s nightlife centers around casual pubs, bistros, and occasional live music in local venues. Guests can unwind with craft beer, locally made wine, or enjoy community events on the town square throughout the year.

  • What are the most popular events or festivals in Leonardtown?

    Leonardtown is known for arts and crafts festivals, seasonal concerts on the square, and community celebrations around Labor Day weekend or during holiday seasons. Local parades and farmers markets are also frequently suggested for a lively introduction to the area.

  • Are there family friendly vacation rentals in Leonardtown?

    Leonardtown has a range of family-friendly vacation rentals, with homes and apartments near local parks and community spaces. Many places include features like kitchens, multiple bedrooms, and access to outdoor areas.

Destinations to explore