Become a host

Vacation rentals in Leonardtown

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Leonardtown

  • Total vacation rentals

    Explore 10 vacation rentals in Leonardtown

  • Nightly prices starting at

    Leonardtown vacation rentals start at $40 per night before taxes and fees

  • Verified guest reviews

    Over 670 verified reviews to help you choose

  • Wi-Fi availability

    10 of Leonardtown vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Leonardtown rentals

  • 4.9 Average rating

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

Top-rated vacation rentals in Leonardtown

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

1 of 1 pages1 / 1
Top guest favorite
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, 127 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!

FamilyLocationLaundry

Top guest favorite
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, 112 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!

FamilyLocationDecor

Top guest favorite
A wooden dock extends over the water, leading to a sun setting on the horizon. Waves gently lap against the sides, reflecting warm hues of orange and pink as the sky transitions into dusk. Two benches are positioned on the dock, inviting peaceful contemplation.
Loft in Lusby
5.0 out of 5 average rating, 421 reviews

Designer owned Coastal getaway retreat

Enjoy our private, above-garage hideaway apartment with private beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home. You have a private entrance. Come and go as you please! Note: We are a peanut-free and smoke free property. RELAX in our chic, private loft just minutes from Chesapeake beaches and 10 minutes from Solomons Island & Calvert Cliffs. You will have private access to our amazing beach just a 5 minute drive away. Please let us know if you plan to use it!

FamilyValueDecor

Top guest favorite
Apartment in Leonardtown
5.0 out of 5 average rating, 18 reviews

The Downtown Leonardtown Hideaway!

✨Stay in the Heart of Downtown Leonardtown and Quick Zip to NAS PAX River, St. Mary's College & CSM. Skip the hotel and settle into your own calm space steps from everything. This cozy condo sits in a quiet, safe neighborhood with sidewalks that lead you straight to the waterfront, eateries, coffee shops, boutiques, and the charm of the historic square. Whether you’re here for a quick escape or work; you’ll love having this space to unwind while being able to walk to all things downtown.

FamilyLocationHospitality

Top guest favorite
Cottage in Leonardtown
4.96 out of 5 average rating, 268 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.

ValueFamilyParking

Top guest favorite
A single-story house is shown with blue siding and white trim, featuring a prominent brick chimney and a welcoming pink door. Large windows provide ample natural light. A grassy area surrounds the home, with trees adding greenery in the background.
Home in Piney Point
5.0 out of 5 average rating, 163 reviews

Living on Island Time

Relax with the whole family and spend life on Island Time. Full bar set up with ice maker and wine refrigerator. Private pier, paddle boards and firepit. Unwind on St Goerge Island or head out to one of the local eateries for some southern Maryland faire. Inside you have 2 spacious rooms, 2 bathrooms. A massive island for cooking, card playing or just great conversations with endless views. Crabbing, fishing. The Neighbors have 2 Great Danes and a cat that you may see occasionally

LocationFamilyTV

Top guest favorite
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, 149 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.

FamilyValueComfort

Top guest favorite
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
4.93 out of 5 average rating, 184 reviews

Little House by the water

Serenity - Privacy - Beauty - This little house by the water has it all. New Sealy queen size mattress, well equipped kitchen, Cuisinart coffee maker, full oven, glass topped stove, new refrigerator, and fully screened porch with water view. Perfect for 1 or 2 adults looking to get off the grid and recharge. In St. Mary's County,MD, just 90 minutes south of Washington DC. However, the space is small and it is really a studio apartment as I think the pictures make evident.

LocationFamilyAccuracy

Top guest favorite
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, 105 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!

ValueLocationGetting around

Top guest favorite
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, 124 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.

FamilyLocationLong stay

Top guest favorite
A view from the entrance captures the cozy interior of the houseboat. The kitchen area features a wooden countertop and a black sink. Light wood and black hexagonal flooring complement the bright space, while large windows provide glimpses of the water outside.
Houseboat in Solomons
4.97 out of 5 average rating, 197 reviews

Good Vibe Villa, Tiny houseboat

This tiny houseboat sits permanently on a boat lift, so you will have the unique experience of being over water without the risk of sea sickness! Located in the heart of quaint Solomons Island, this is a great stay if you love being near the water. Unparalleled views from your private porch. Please note, due to extensive pet damage we have changed this property to strictly no animals. You will be asked to leave if you arrive with a pet.

LocationFamilyBiking

Top guest favorite
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, 137 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”).

LocationFamilyIndoor spaces

Popular amenities for Leonardtown vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Leonardtown's top sights

Port of Leonardtown Winery

43 locals recommend

Leonardtown Wharf

41 locals recommend

Olde Town Pub

32 locals recommend

Other great vacation rentals in Leonardtown

Guest favorite
Home in Leonardtown
4.94 out of 5 average rating, 32 reviews

Waterfront Retreat | Sunset Views (Pet friendly)

LocationFamilyKitchen

Guest favorite
Home in Leonardtown
4.89 out of 5 average rating, 27 reviews

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

FamilyLocationNearby

Top guest favorite
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
4.94 out of 5 average rating, 36 reviews

Potomac Fishing & Crab Paradise at Toney's Landing

LocationFamilySleep quality

Top guest favorite
A private balcony extends from the studio, offering seating for relaxation. Breathtaking waterfront views of the serene landscape and grassy shoreline are visible beyond the railings, surrounded by trees that add a natural touch to the outdoor space.
Home in Piney Point
4.99 out of 5 average rating, 70 reviews

Waterfront Studio | Bikes & Kayaks | Beach Access

FamilyLocationWifi

Guest favorite
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, 96 reviews

The River House: A private waterfront oasis…

LocationFamilyOutdoor spaces

Top guest favorite
A spacious bedroom features a light-colored bed with a floral-patterned coverlet. A small nightstand and a lamp provide soft lighting. Large glass doors open to a serene outdoor view, with a light green wall and plush carpet completing the inviting space.
Guesthouse in Leonardtown
5.0 out of 5 average rating, 54 reviews

Breton Bay Guesthouse ~ ~ No cleaning fee

ValueLocationView

Top guest favorite
A wooden pier extends over calm waters, leading towards a grassy area lined with trees. Rustic cottages are visible in the background, framed by lush greenery. Sunlight highlights the natural textures of the pier and the surrounding landscape.
Cottage in Tall Timbers
5.0 out of 5 average rating, 76 reviews

Charming Waterfront Cottage with Sunset Views

FamilyLocationRiver

Superhost
Home in Leonardtown
4.79 out of 5 average rating, 14 reviews

Hidden Harbor House

LocationFamilyView

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