St. Leonard vacation rentals

We found 120 vacation rentals — enter your dates for availability

Discover a selection of 14 homes and other vacation rentals in St. Leonard that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation homes have the best amenities for hanging out with the people that matter most, which might include cable TV and a washer and dryer. You'll be sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.
Showing deals for:Nov 7 - Nov 14
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Find out more about St. Leonard

Find out more about St. Leonard

Why visit St. Leonard

  1. Stunning Beaches: Enjoy the beautiful shoreline and relax at the sandy beaches, perfect for a day of sun and fun.
  2. Outdoor Adventures: Explore numerous urban parks and scenic trails ideal for hiking, biking, and nature walks.
  3. Historic Lighthouses: Visit iconic lighthouses that showcase the rich maritime history of the area.
  4. Charming Suburbs: Discover vibrant neighbourhoods filled with art, culture, and friendly locals.
  5. Diverse Accommodations: Choose from a variety of vacation rentals, including cozy cottages and rustic cabins.

Popular types of accommodation in St. Leonard

Discover the charm of St. Leonard with a variety of vacation rentals tailored to your needs. Whether you're looking for houses, cozy cottages, or rustic cabins, we've got you covered. Our platform offers transparency, savings, and reassurance as you explore options like Léonard rentals and Léonard apartments for rent. Find the perfect Leonard vacation rental that suits your getaway plans and enjoy your stay in this beautiful Canadian locale.

  • Houses: The top choice for visitors in St. Leonard, offering spacious and comfortable accommodations ideal for families or groups.
  • Cottages: A charming option, these quaint retreats provide a cozy atmosphere for a relaxing getaway.
  • Cabins: Perfect for those seeking a rustic experience, cabins in St. Leonard offer a unique connection to nature.
  • Apartments: Convenient and modern, apartments are great for solo travellers or couples wanting easy access to local amenities.
  • Villas: Luxurious and spacious, villas cater to those looking for an upscale vacation experience.**

Top attractions in St. Leonard

St. Leonard, Maryland, is perfect for outdoor and adventure vacations, offering beautiful scenery and a variety of attractions. Popular points of interest include the stunning beach, urban parks, and historic lighthouses. Whether you're seeking a family-friendly outing or a vibrant city experience, St. Leonard has something for every traveller to enjoy during their visit.

  1. Calvert Cliffs State Park: Located 11.3km from St. Leonard, this park features stunning cliffs and scenic views, perfect for hiking and exploring the outdoors. Keep an eye out for fossil hunting along the shoreline!
  2. Jefferson Patterson Park and Museum: Situated within St. Leonard, this national park offers a blend of adventure and educational experiences, showcasing the area's rich history and beautiful landscapes.
  3. Breezy Point Beach: Found 16.1km away, this charming beach offers a relaxing atmosphere with sandy shores ideal for sunbathing, swimming, and enjoying the coastal vibe.

Things to do recommended for couples

For a romantic getaway in St. Leonard, explore Perigeaux Vineyards and Winery for its charming ambiance and delightful wines. Alternatively, enjoy a fun round at R&J's PlayPark mini-golf, or visit Running Hare Vineyard, where you can relax and sip exquisite wines together amidst beautiful scenery.

Things to do recommended for families

Families can splash around at Chesapeake Beach Water Park, located 24.1km from St. Leonard. With its thrilling slides and family-friendly atmosphere, it promises a day full of fun and adventure for kids and adults alike.

Things to do recommended for groups

Experience the thrill of motorsports at Maryland International Raceway or Budds Motorcross Speedway, both offering adventure and excitement. For a more relaxed outing, visit Fox Run Center, a local shopping hub perfect for family and group activities, just a short drive from St. Leonard.

What do I need to keep in mind when booking a vacation in St. Leonard

If you're planning a trip with a group, family, or pets, or if you’re interested in extended stays, be sure to refine your search based on your key priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to St. Leonard with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to St. Leonard with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with seeking out suitable amenities like a private swimming pool. Additionally, keeping in mind your distance to family-friendly attractions can enhance your travel experience.
  • Taking your pets with you to St. Leonard: For many, a family getaway wouldn’t feel complete without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting St. Leonard: If you're in search of vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in St. Leonard

St. Leonard, Maryland, offers a delightful blend of outdoor adventures and family-friendly experiences. Explore the charming nearby suburbs, where you can soak in the vibrant atmosphere filled with art and friendly locals. The region is perfect for excursions, allowing travellers to enjoy the scenic beauty and welcoming neighbourhood vibes. Whether you're seeking relaxation or adventure, St. Leonard and its surrounding areas promise an unforgettable getaway.

  • Prince Frederick: Located a mere 9.7km from St. Leonard, Prince Frederick is a vibrant city that beckons outdoor enthusiasts and those seeking adventure. The area is well-known for its scenic beauty, with attractions such as the local racetrack and picturesque cliffs overlooking the beach. Visitors can indulge in motor racing experiences or unwind in the recreational areas while exploring shopping centres that offer a variety of local goods and services. The combination of thrilling activities and serene landscapes makes Prince Frederick a great spot for a day trip or longer stay.
  • Port Republic: Just 3.2km away from St. Leonard, Port Republic is a charming city that invites visitors to immerse themselves in nature and adventure. Its stunning cliffs and family-friendly beaches provide an idyllic backdrop for outdoor activities. With opportunities for education and motor racing, this community offers a perfect blend of fun and knowledge. Travelers can enjoy the recreational areas while taking in the beautiful scenery, making Port Republic a delightful destination for families and individuals alike.
  • Calvert Beach-Long Beach: Nestled within the area of St. Leonard, Calvert Beach-Long Beach is a quaint village renowned for its outdoor activities and breathtaking scenery. Visitors can explore the scenic boardwalk and hiking trails that connect to the stunning cliffs and pristine beaches. The nearby national state park offers ample opportunities for nature lovers to engage in hiking and wildlife observation. This charming village is perfect for those looking to relax and recharge while soaking in the natural beauty of the Maryland coast.

Best time to go to St. Leonard

If you're planning a trip to St. Leonard, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like December to February tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January36.1°F (2.3°C)Light RainMostly SunnyLowSlightly Low
February39.0°F (3.9°C)Light RainMostly SunnyLowSlightly Low
March45.7°F (7.6°C)Light RainMostly SunnyAverageSlightly Low
April55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
May64.8°F (18.2°C)Light RainMostly SunnyAverageAverage
June73.2°F (22.9°C)Light RainMostly SunnyHighSlightly High
July78.3°F (25.7°C)Light RainMostly SunnyHighSlightly High
August76.5°F (24.7°C)Light RainMostly SunnyHighSlightly High
September70.5°F (21.4°C)Light RainMostly SunnyAverageAverage
October60.3°F (15.7°C)Light RainMostly SunnyAverageAverage
November48.6°F (9.2°C)Light RainMostly SunnyAverageAverage
December41.7°F (5.4°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that suits your budget, feel free to use our filters to narrow down your options by price, location, and type of vacation rental. We're here to help you find the perfect fit!

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new journeys, pick up from where you last paused, or review and arrange your travel plans. You can easily access properties you've saved or booked, now categorized under Potential, Upcoming, or Current Trips. To explore the Trip Boards, visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Find the perfect vacation rental for your St. Leonard getaway

The area's wineries and museums are just a few of the reasons to vacation in St. Leonard. This city's shopping, sporting events and restaurants draw many visitors. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in St. Leonard

Do you want to discover top things to see and do in the area? Venture out of your vacation home and check out everything that makes St. Leonard a one-of-a-kind vacation spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Running Hare Vineyard (6.7 mi / 10.8 km)
  • Port of Leonardtown Winery (14.3 mi / 23.1 km)
  • Chesapeake Beach Water Park (15.1 mi / 24.3 km)
  • Maryland International Raceway (18.3 mi / 29.5 km)
  • Michael P. O'Brien Athletics and Recreation Center (20.2 mi / 32.5 km)
  • Perigeaux Vineyards and Winery (3.8 mi / 6.1 km)

Exploring the natural landscape of St. Leonard

Whether you're an adventurous traveler or just want to spend some time taking in the scenery, St. Leonard is a great place to get out in nature. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Matoaka Beach (1.5 mi / 2.4 km)
  • Flag Ponds Nature Park (2.9 mi / 4.6 km)
  • Battle Creek Cypress Swamp Sanctuary (4.7 mi / 7.5 km)
  • Annmarie Sculpture Garden and Arts Center (9.4 mi / 15.1 km)
  • Breezy Point Beach (10.1 mi / 16.3 km)
  • Seahorse Beach (10.9 mi / 17.6 km)

Transportation to and around St. Leonard

The nearest airport is in Ronald Reagan Washington National Airport (DCA), located 38.8 mi (62.4 km) from the city center.

Frequently asked questions

What is the most popular type of vacation rental accommodation in St. Leonard?
According to our data, houses are the most popular type of vacation property in St. Leonard. But as you know, everyone's idea of the perfect trip will differ. Vrbo has vacation homes of all shapes, sizes and budgets, so you're sure to discover the best fit for your needs.
How much does it cost to rent a vacation rental in St. Leonard?
The average price for a vacation rental in St. Leonard depends on a number of factors, including length of stay, property type and season. Whether you're in search of a sprawling villa with space for extended family or a quaint cabin perfect for just you and the kids, just add your dates of travel to find stays with amazing value.
How much does it cost to rent a beach house in St. Leonard?
The average price for a vacation home close to the beach in St. Leonard depends on when you're traveling and the size and type of property you're searching for. Find prices quickly and easily on Vrbo by entering the dates you'll be traveling. Then use our handy filter tool to pick the number of bedrooms and amenities that you prefer, like air conditioning, a pool and WiFi.
Are there pet-friendly vacation rentals in St. Leonard?
Good news! Yes. You'll have a choice of six vacation rentals that allow pets in St. Leonard. Some of our pet-friendly vacation rentals have an outdoor space for your four-legged fur baby to have fun in, complimentary treats, special dog beds and proximity to parks. Apply the "Pets allowed" filter to find your pawfect digs on Vrbo.
What are popular rental amenities in St. Leonard?
Nearby museums, a nearby waterfront and a water view top the list of most popular rental amenities in St. Leonard. Whether you plan to travel by yourself, with your significant other or a group of best friends, Vrbo will help you find a vacation rental that fits your style with all the features you'll enjoy.
Are there large group vacation rentals in St. Leonard?
With three St. Leonard vacation properties that can accommodate five or more people, you can bring a few extra pals or family members along. Whether you're planning an informal get-together or a celebratory event, we'll help you find a comfy space to match the occasion.
Are there vacation rentals in St. Leonard that welcome kids?
With six family-friendly vacation homes available in St. Leonard, now is an awesome time to introduce your children to the joys of travel. Simply click on our "Properties good for families" filter box to search for stays loaded with amenities ideal for vacationing families, like multiple bedrooms, backyards, bunk beds and entertainment areas.
What are the top attractions for families in St. Leonard?
Keeping the kids amused during your vacation in St. Leonard is easy with these fabulous family-friendly attractions:

  • R&Js PlayPark
  • Jefferson Patterson Park and Museum
  • Battle Creek Cypress Swamp Sanctuary

Can I find two-bedroom vacation rentals in St. Leonard?
Take off with your besties and relax in total privacy and comfort in one of the three two-bedroom vacation rentals St. Leonard has to offer.
Are there vacation rentals with WiFi in St. Leonard?
St. Leonard has two vacation rentals with WiFi, so you can stay connected while you're away. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming Hollywood blockbusters to updating your social media, these Vrbo homes make it easy to go online.
How can I find vacation rentals with air conditioning in St. Leonard?
You can choose from six Vrbo vacation rentals with air conditioning in St. Leonard giving you that cool, cool breeze and extra level of comfort. Enter your chosen travel dates and then make use of our filter tool to find stays with air conditioning.
How old do you have to be to rent a vacation rental in St. Leonard?
The age limit can differ across properties on Vrbo, so look at the rules of the vacation rental in St. Leonard you're interested in. But usually, it's 16, 18 or 21.
How long can I rent a vacation rental in St. Leonard for?
The amount of time you can stay in a St. Leonard vacation home for differs depending on the property. Simply tap in your travel dates to view options offering extended stays. They have all you require to make your extended trip more enjoyable and convenient, like kitchens and backyards. Some properties might also offer weekly or monthly discounts, so you can stay longer for less money.

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