St. Leonard vacation rentals

We found 123 vacation rentals — enter your dates for availability

Discover a selection of 16 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.

Vacation rentals with weekly discounts - St. Leonard

Showing deals for:Apr 3 - Apr 10

Image gallery for Cottage Located on the Patuxent River!

Room
10 out of 10, Exceptional, (42 reviews)
Exceptional
(42 reviews)

Cottage Located on the Patuxent River!

Prince Frederick

9% off
Price is $295
$2,067 for 7 nights
All fees included
Cottage Located on the Patuxent River!

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Find out more about St. Leonard

Why visit St. Leonard

  • Outdoor Adventure: St. Leonard is perfect for outdoor enthusiasts, offering activities like hiking along the coastline and exploring urban parks.
  • Scenic Beauty: Experience the picturesque landscapes of Calvert County, with beautiful beaches and charming neighborhoods.
  • Family-Friendly Vibes: The area caters to families, providing a range of recreational activities suitable for all ages.
  • Welcoming Community: Enjoy the friendly atmosphere and memorable excursions that highlight local culture.
  • Diverse Accommodations: Choose from private vacation homes, cozy cottages, and charming cabins for a perfect getaway.

Popular types of accommodation in St. Leonard

If you're exploring vacation rentals in St. Leonard, you're in for a treat. Our most sought-after accommodations include houses, cozy cottages, and charming cabins. Whether you're looking for spacious house rentals, comfortable vacation homes, or intimate studio apartments, we have options to suit every traveler's needs. Discover your perfect getaway in St. Leonard and enjoy a memorable stay.

  • Houses: The top choice for visitors in St. Leonard, offering spacious and comfortable stays for families or groups.
  • Cottages: A charming option, these cozy accommodations provide a delightful retreat for couples or small families.
  • Cabins: Ideal for those seeking a rustic experience, cabins blend nature with comfort for a unique getaway.
  • Apartments: Convenient and versatile, these rentals are perfect for travelers wanting a home-like atmosphere.
  • Villas: Luxurious options that cater to those looking for upscale amenities and beautiful surroundings.**

Top attractions in and around St. Leonard

St. Leonard, Maryland, is perfect for outdoor enthusiasts seeking adventure and scenic beauty. Visitors can explore a variety of attractions, including urban parks, beautiful beaches, and marinas. Whether you're traveling with family or looking for a city experience, St. Leonard offers a range of activities that cater to all types of travelers, making it an ideal destination for a memorable vacation.

  • Calvert Cliffs State Park: Explore stunning 130-foot cliffs along the Chesapeake Bay, perfect for hiking and fossil hunting. The park offers breathtaking views of the water and diverse wildlife, making it an outdoor enthusiast's paradise.
  • Jefferson Patterson Park and Museum: This historical park features archaeological exhibits and scenic trails. Enjoy outdoor activities while learning about Maryland's rich history and heritage in a picturesque setting.
  • Breezy Point Beach: Relax on the sandy shores of Breezy Point Beach, ideal for sunbathing and swimming. The serene atmosphere and beautiful views provide a perfect beach getaway.

Things to do recommended for couples

Planning a romantic getaway in St. Leonard? Begin with a wine tasting at Perigeaux Vineyards and Winery, then enjoy some fun at R&J's PlayPark mini-golf, just 6 miles away. Finally, take a scenic stroll along the Solomons Island Boardwalk, 11 miles away, and soak in the beautiful views.

Things to do recommended for families

Families visiting St. Leonard can have a blast at Chesapeake Beach Water Park, just 15 miles away. This vibrant waterpark offers thrilling slides, relaxing pools, and plenty of family-friendly entertainment for a perfect day of fun and adventure.

Things to do recommended for groups

Experience the thrill of motor racing at the Maryland International Raceway and Budds Motorcross Speedway, both offering an exciting adventure just 18 miles from St. Leonard. For a more relaxed outing, visit the Wildewood Shopping Center, located 11 miles away, perfect for shopping and dining with family and friends.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When planning your trip, whether you're traveling with a group, family, or pets, or seeking extended stays, be sure to use the appropriate filters to align with your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to St. Leonard with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor areas for group gatherings. The good news is that you can easily filter for these options and much more on Vrbo.
  • Traveling to St. Leonard with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to St. Leonard: For many families, a vacation isn't truly complete without their furry companion. If you can relate, explore Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting St. Leonard: If you’re searching for vacation rentals offering discounts 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 criteria.

Where to stay near St. Leonard

St. Leonard, Maryland, offers a perfect blend of outdoor adventure and family-friendly vibes. Explore the scenic beauty of Calvert County, with its coastal living and charming neighborhoods like East Sussex. Enjoy recreational activities, friendly locals, and memorable excursions that highlight the area's welcoming atmosphere. Whether you're hiking along the coastline or relaxing in a nearby park, St. Leonard provides a delightful escape for travelers seeking both adventure and relaxation.

  • Prince Frederick: Located 6 miles from St. Leonard, Prince Frederick offers a delightful blend of outdoor adventure and scenic beauty. This vibrant city is known for its recreational areas where visitors can engage in motor racing and enjoy the local shopping center. The area is surrounded by beautiful landscapes, including cliffs and beaches, providing stunning views that are perfect for a day of exploration. Whether you're racing at the local racetrack or relaxing on the beach, Prince Frederick promises an exhilarating experience for all travelers.
  • Port Republic: Just 2 miles away from St. Leonard, Port Republic is a charming city that invites visitors to immerse themselves in the great outdoors. Known for its scenic cliffs and inviting beaches, this area is perfect for those seeking adventure. Popular activities include exploring the local recreational areas and engaging in educational experiences. Families will appreciate the family-friendly beach options, making Port Republic an ideal destination for a day of fun and relaxation by the water.
  • Solomons: Situated 11 miles from St. Leonard, Solomons is a picturesque city renowned for its breathtaking scenery and outdoor activities. Visitors can enjoy a variety of attractions, including recreational areas and educational venues, as well as the thrill of motor racing. The nearby cliffs and pristine beaches make Solomons a perfect spot for picturesque walks and memorable sunsets. With a blend of adventure and relaxation, Solomons is a must-visit destination for those looking to experience the natural beauty of Maryland.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 a breeze

Are you eager to save on your upcoming journey? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking an extended stay for even greater savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on the full booking amount. Being the planner truly has its rewards. When you join our travel rewards program, One Key, you'll gain access to exclusive discounts and earn OneKeyCash on eligible bookings. Sign up today and begin your journey to savings.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, keep your travel arrangements on track, and manage your bookings effectively. Your saved or reserved properties are conveniently categorized into Potential, Upcoming, or Current Trips. To start exploring your Trip Boards, simply visit: https://www.vrbo.com/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)
  • 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)
  • Chesapeake Hills Golf Course (7.7 mi / 12.4 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)
  • Long Beach (2 mi / 3.2 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)

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 best area to stay in St Leonard when booking a vacation rental?
When considering a vacation rental in St. Leonard, Maryland, the best area to stay is near the waterfront along the Patuxent River. This region not only offers picturesque views but also provides easy access to outdoor activities, making it ideal for those who enjoy nature and water sports.

In this area, you can explore attractions such as the nearby Calvert Cliffs State Park, famous for its fossil-laden cliffs and scenic hiking trails. This park is great for families looking to spend a day outdoors, as it features trails that lead to a beautiful beach where you can hunt for fossils. Another point of interest is the historic St. Leonard's Church, which adds a touch of local heritage and charm to your stay.

The waterfront neighborhoods tend to have a variety of vacation rental options, ranging from cozy cottages to spacious homes, allowing you to find a property that suits your needs.
How much does it cost to rent a vacation home in St Leonard?
Prices for vacation rentals in St Leonard vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in St Leonard to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for St Leonard vacation house rentals?
You can find great discounts on house rentals in St Leonard on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in St Leonard?
For renting a beach house in St. Leonard, Maryland, travelers should focus on the scenic waterfront along the Chesapeake Bay. The area around St. Leonard Creek offers picturesque views and a variety of rental options, including cozy cottages and spacious homes that cater to families and groups. Many of these properties come equipped with modern amenities such as private docks, outdoor grilling areas, and large decks, great for enjoying the bay's tranquility and sunsets.

Additionally, the nearby Calvert Cliffs State Park provides an opportunity for outdoor activities, including hiking and beachcombing along the natural shoreline. Rentals in this area often feature easy access to the park, with some homes boasting amenities like fire pits and picnic areas, enhancing the outdoor experience. The charming community of St. Leonard also offers local shops and restaurants, making it convenient for travelers to enjoy the local cuisine and culture.
What is the most popular type of vacation rental accomodation in St Leonard?
In St. Leonard, vacation houses are the most popular type of rental, with around 14 available throughout the area. These houses typically provide spacious living arrangements, including multiple bedrooms, fully equipped kitchens, and outdoor spaces for gatherings. In addition to vacation houses, there are several cottages and apartments that offer a cozy, home-like atmosphere. Cottages often feature charming interiors and may include amenities like fireplaces and private yards, while apartments provide convenient access to local attractions with essential facilities for a comfortable stay.
Are there any family house rentals in St Leonard?
In St. Leonard, Maryland, there are some family-friendly house rentals to choose from. This charming area offers a blend of natural beauty and local attractions, making it an excellent destination for families. Properties in the vicinity typically feature spacious layouts, fully equipped kitchens for preparing meals together, and outdoor areas for kids to enjoy.

Visitors can explore the nearby beaches along the Chesapeake Bay, superb for swimming and picnicking, or take advantage of the local parks that provide playgrounds and open spaces for recreational activities. The tranquil environment also allows for relaxing family gatherings and outdoor adventures, ensuring a memorable stay for all ages.
Can I rent a vacation home with a pool or hot tub in St Leonard?
In St. Leonard, Maryland, there are several vacation homes available for rent that feature pools and hot tubs, making it a great choice for travelers seeking relaxation and leisure. This charming area, located along the Patuxent River, offers a mix of waterfront and inland properties. Many rentals come equipped with private pools, spacious outdoor decks, and hot tubs, ideal for unwinding after a day of exploring the beautiful surroundings.

Travelers can expect amenities such as fully equipped kitchens, comfortable living spaces, and outdoor grilling areas, great for family gatherings or group retreats.
Can I find long-stay vacation rentals in St Leonard?
A long-stay vacation rental in St Leonard is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in St Leonard?
In St. Leonard, there are several pet-friendly house rentals available for travelers looking to enjoy a getaway with their furry companions. Many of these vacation homes come equipped with spacious outdoor areas, great for pets to roam and play, as well as amenities like fully equipped kitchens, comfortable living spaces, and sometimes even private decks or patios for relaxation.

The area is known for its proximity to the beautiful Chesapeake Bay, where visitors can take scenic walks along the waterfront and enjoy picturesque views. Additionally, nearby parks and nature trails provide opportunities for outdoor activities with pets, making it a great choice for those who want to combine relaxation with adventure.
Are there any remote work vacation rentals in St Leonard?
In St. Leonard, Maryland, there are numerous vacation rentals suitable for remote work, with around 19 options available. These rentals typically offer essential amenities that cater to working professionals, including reliable Wi-Fi, dedicated desks, and comfortable office chairs. Some properties are equipped with additional features such as laptop workspaces, computer monitors, and safes for secure storage of personal items.

The area is known for its serene environment, making it an ideal spot for those looking to balance work and relaxation. Located near the Chesapeake Bay, you can enjoy beautiful waterfront views and outdoor activities during your downtime. Many rentals also provide spacious living areas and kitchens, allowing for a comfortable extended stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any St Leonard vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in St Leonard with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in St Leonard?
In St. Leonard, popular vacation rental amenities include WiFi, which is essential for staying connected, and kitchens that allow guests to prepare their own meals. Many rentals feature blenders and coffee/tea makers, making it easy to enjoy a fresh breakfast or a quick snack. Additionally, kitchen islands are common, providing extra space for cooking and dining.
When is the best time to visit St Leonard for a vacation rental?
The best time to book a vacation rental in St. Leonard is during the summer months, particularly in July. This peak season, which spans from July to September, attracts visitors eager to enjoy the area's beautiful waterfront and outdoor activities. With warm temperatures averaging in the low 70s to mid-80s Fahrenheit, the summer provides ideal conditions for swimming, kayaking, and exploring the picturesque beaches along the Chesapeake Bay.

July stands out as a favorite among travelers, offering a vibrant atmosphere filled with community events and opportunities for relaxation. It's an excellent time for families and friends to gather, with plenty of options for both leisure and adventure just a stone's throw away. The local parks and nature trails are also superb for hiking and enjoying the scenic views that St. Leonard has to offer.

For those considering a more budget-friendly visit, November presents a unique opportunity. The fall season brings a quieter ambiance, allowing for peaceful strolls along the shoreline and the chance to appreciate the beauty of autumn without the summer crowds. This time of year is superb for reflective nature walks and enjoying the serene landscape.

Ultimately, your choice will depend on whether you prefer the lively summer atmosphere filled with activities or the tranquil charm of the off-peak months.
How early should I book a St Leonard vacation rental?
Book your St Leonard vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in St Leonard?
In St. Leonard, Maryland, visitors can enjoy a variety of attractions centered around its natural beauty and recreational opportunities. The Calvert Cliffs State Park is a highlight, offering hiking trails and access to the beach where fossil hunting can be a fun activity. The nearby Chesapeake Bay is great for water-related activities like kayaking and fishing.

For those interested in history, the St. Leonard's Church, which dates back to the 18th century, provides a glimpse into the area's past. Additionally, the community's charming local shops and eateries can be explored, enhancing the experience of staying in this picturesque region.

The surrounding areas, such as Solomons Island, also offer waterfront dining and the Calvert Marine Museum, making it a great day trip for those staying in St. Leonard.
Can I change or cancel my St Leonard home rental booking on Vrbo?
To find St Leonard vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the St Leonard vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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