St. Mary's County vacation rentals

We found 493 vacation rentals — enter your dates for availability

Select from 72 homes, 41 cottages, and other vacation rentals in St. Mary's County to find one that's perfect for your trip. Vacation homes provide the amenities you need and want for your stay with friends, family, or just your pet, such as WiFi and a pool. At the end of the day, you'll be able to choose a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Popular St. Mary's County destinations on Vrbo

Vacation rentals with weekly discounts - St. Mary's County

Showing deals for:Sep 19 - Sep 26

Find out more about St. Mary's County

Find out more about St. Mary's County

Why visit St. Mary's County

  1. Outdoor Adventures: Enjoy a range of activities in urban parks, state parks, and beautiful beaches ideal for nature lovers.
  2. Historical Exploration: Discover the rich history of St. Mary's City, offering a glimpse into the past.
  3. Scenic Views: Experience breathtaking landscapes that provide perfect backdrops for relaxation and photography.
  4. Charming Neighborhoods: Explore picturesque towns with friendly locals and a welcoming atmosphere.
  5. Family-Friendly Activities: Engage in diverse experiences suitable for both families and solo travelers.

Top attractions in St. Mary's County

St. Mary's County, Maryland, is perfect for outdoor enthusiasts and those seeking a romantic getaway. With a variety of attractions such as urban parks, national and state parks, and beautiful beaches, it offers a diverse experience for families and solo travelers alike. Whether you’re looking to explore nature or enjoy the charm of the city, St. Mary's County promises memorable adventures and scenic views that cater to all types of visitors.

  1. St. Mary's College of Maryland: This historic college offers a blend of academic excellence and rich culture, with beautiful campus grounds and engaging events that reflect the area's heritage.
  2. Point Lookout State Park: A haven for outdoor enthusiasts, this park features stunning scenery, hiking trails, and fishing opportunities, all set against the backdrop of the Chesapeake Bay.
  3. Piney Point Beach: A serene beach perfect for relaxation, swimming, and picnicking, providing a lovely atmosphere to soak up the sun and enjoy the coastal views.

Things to do recommended for couples

If you're seeking romance in St. Mary's County, visit the Port of Leonardtown Winery. Enjoy the enchanting atmosphere as you sip on local wines, surrounded by beautiful scenery. It's the perfect spot for couples to unwind and create lasting memories together.

Things to do recommended for families

Families will love Elms Beach Park, a serene recreation area in St. Mary's County. Enjoy outdoor activities, relax by the water, and soak in the wellness vibes that make it a perfect spot for a family outing.

What do I need to keep in mind when booking a vacation in St. Mary's County

When traveling with a group, family, or pets, or if you're seeking extended stays, it's important to filter your options based on what matters most to you. Here are some helpful tips for booking on Vrbo.

  • Traveling to St. Mary's County with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to St. Mary's County with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to St. Mary's County: For many families, a vacation isn’t truly fulfilling without their furry companion by their side. If that resonates with you, explore the Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting St. Mary's County: If you're in search of vacation rentals that offer 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 rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search to enhance your experience.

Where to stay in St. Mary's County

St. Mary's County, Maryland, offers a delightful blend of outdoor adventures and scenic beauty, making it perfect for a romantic getaway or family-friendly excursions. Explore charming towns like St. Mary's City, rich in history, or relax by the water in picturesque neighborhoods. With friendly locals and a laid-back atmosphere, visitors can enjoy a relaxing vacation filled with unique experiences and stunning landscapes. Discover why this hidden gem is a must-visit destination!

  • California: California is a charming city located in St. Mary's County, known for its outdoor adventures and stunning scenery. Visitors are drawn to the area for activities like motor racing and exploring recreational parks. The local attractions include a historic racetrack, a renowned college university, and scenic cliffs that offer breathtaking views. Whether you’re looking to enjoy an adrenaline-pumping race or simply relax in nature, California provides a delightful getaway for adventure seekers and nature lovers alike.
  • Lexington Park: Lexington Park is a vibrant city that combines culture and outdoor experiences, making it a popular destination in St. Mary's County. This area is perfect for visitors seeking a mix of educational and recreational activities, including access to a historic college university and beautiful beaches. The local racetrack adds excitement for motorsport enthusiasts, while the various parks provide ample space for relaxation and outdoor fun. Lexington Park’s rich cultural scene and diverse attractions make it a must-visit for those looking to immerse themselves in the local charm.
  • Leonardtown: Leonardtown is the picturesque county seat of St. Mary's County, offering a unique blend of outdoor activities and scenic beauty. Travelers are attracted to this quaint city for its recreational areas, beautiful lakes, and proximity to national and state parks. Enjoy a day at the beach or hike through lush landscapes while taking in the area's natural allure. Leonardtown’s relaxed atmosphere and charming local attractions make it an ideal spot for a tranquil escape, perfect for both adventure enthusiasts and those seeking a peaceful retreat.

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often result in significant discounts. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your entire booking. Being the planner definitely has its perks! 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 start enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a user-friendly platform for planning your trips. You can easily start new trips, pick up from where you last stopped, or view and organize your travel plans all in one place. Your saved or booked properties will be conveniently organized into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

Choose a vacation rental for your St. Mary's County getaway

Learn about the unique charm of St. Mary's County with a stay in a private vacation home. There's no shortage of things to see and do in the area.If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around St. Mary's County

Are you hoping to discover things to do during your stay? Venture out of your vacation home and experience everything that St. Mary's County has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Perigeaux Vineyards and Winery (11.2 mi / 18.1 km)
  • Maryland International Raceway (13 mi / 21 km)
  • Running Hare Vineyard (15.1 mi / 24.3 km)
  • Ingleside Vineyards (21.8 mi / 35.1 km)
  • Ingleside Vineyards (22.2 mi / 35.8 km)
  • White Plains Golf Course (25.1 mi / 40.4 km)

Exploring the natural landscape of St. Mary's County

Whether you're an adventurous traveler or just want to appreciate the scenery, St. Mary's County is a great place to get out in nature. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • St. Mary's River State Park (5.1 mi / 8.2 km)
  • St. Clement's Island State Park (8 mi / 12.9 km)
  • Annmarie Sculpture Garden and Arts Center (10.5 mi / 16.9 km)
  • Piney Point Beach (12.2 mi / 19.6 km)
  • Cove Point Beach (14.8 mi / 23.9 km)
  • Matoaka Beach (15 mi / 24.2 km)

Frequently asked questions

What is the best area to stay in St. Mary's County when booking a vacation rental?
If you're thinking about a stop in St. Mary's County, Mechanicsville is one of the most sought-after areas to book a vacation home. While you're here, pay a visit to awesome sights like Maryland International Raceway and Budds Motorcross Speedway.
What is the most popular type of vacation rental accommodation in St. Mary's County?
The most in-demand types of vacation rentals in St. Mary's County are cottages. Ready for more choices? Vrbo has plenty of options to match our guests' unique requirements, so you'll see properties in all sizes, and for all budgets. The ideal home away from home is waiting for you --- discover yours today.
How much does it cost to rent a vacation rental in St. Mary's County?
Season, property type and length of stay are some factors that can affect the price of a vacation home. Simply click on your travel dates to find the ultimate escape. From quaint country cottages to sprawling villas, all Vrbo vacation rentals offer terrific value.
How much does it cost to rent a beach house in St. Mary's County?
The average price for a vacation home by the beach in St. Mary's County depends on when you'll be there and the type and size of property you want. You can find prices easily and quickly on Vrbo by entering your travel dates and destination. Then make use of the filter tool to select the number of bedrooms and amenities that you prefer, such as air conditioning, WiFi and a pool.
Are there pet-friendly vacation rentals in St. Mary's County?
Yes. There are. You can choose from 30 vacation rentals that allow pets in St. Mary's County on Vrbo. Our furry friends deserve a getaway too, so simply use our search function for pet-friendly vacation rentals to find a property where Fido can be near his favorite humans.
Are there large group vacation rentals in St. Mary's County?
With 19 properties that can host 10 people or more in St. Mary's County, you won't have to keep your invite list short. From extended family vacations to special events like Thanksgiving or Christmas parties, Vrbo will help you find a large group rental to match the occasion.
What are the top attractions for families in St. Mary's County?
Keeping the kids happy during your St. Mary's County vacation is a breeze with these top family-friendly attractions:
  • Point Lookout State Park
  • Budds Motorcross Speedway
  • Maryland International Raceway

Are there one-bedroom vacation rentals in St. Mary's County?
Yes, you'll find 8 one-bedroom properties in St. Mary's County to pick from. A one-bedroom vacation property is an excellent option if it's just you and your sweetheart or if you're flying solo. Toss in more convenience, space and privacy compared to a regular hotel, and you've got yourself a memorable getaway.
Can I find two-bedroom vacation rentals in St. Mary's County?
St. Mary's County has 15 two-bedroom vacation properties for you to select from. Go for a vacation home with all the comfort and space you want at a fantastic price on Vrbo.
Are there vacation rentals with WiFi in St. Mary's County?
Whether you'd like to keep up with the latest news, reply to emails or surf social media, there are 36 vacation homes with WiFi in St. Mary's County. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in St. Mary's County?
St. Mary's County has 71 vacation rentals where you can chill out in air-conditioned comfort. To find a property on Vrbo offering this amenity, choose your travel dates and use the filter tool to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in St. Mary's County?
The minimum age can differ between properties on Vrbo, so be sure to look at the rules of the vacation home in St. Mary's County you're considering. But in general, it's 16, 18 or 21.
How long can I rent a vacation rental in St. Mary's County for?
The length of time you can book a vacation rental in St. Mary's County depends on the property. Just enter your chosen travel dates to see a list of options offering extended stays. With many amenities such as air conditioning and laundries, as well as some offering weekly or monthly discounted prices, you're sure to find somewhere perfect to call your home away from home in St. Mary's County.
Does Vrbo offer discounts for vacation homes in St. Mary's County?
In St. Mary's County, you'll find some fantastic discounts and deals for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you're wanting a mini vacay or a much longer stay, we've got plenty of options to suit your style.

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