Discover Your Ideal St. Mary's County, Maryland Vacation Rentals for a Memorable Getaway
Discover Your Perfect St. Mary's County Vacation Homes
Best Vacation Homes in St. Mary's County
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St. Mary's County Luxury Rentals
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St. Mary's County Pet Friendly Vacation Rentals
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St. Mary's County Large Vacation Homes
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Why Choose Rent By Owner for your St. Mary's County Vacation Rental Homes?
What makes our Vacation Rentals special?
Best Times to Visit St. Mary's County
When should you plan your Vacation Rentals stay?
Choosing the optimal time to vacation in this destination ensures you experience its best weather and local events, making your stay in the area truly memorable.
Peak Season Highlights
Late Spring to Early Summer (May - June)
This is the most popular time to visit, as you can enjoy warm weather and outdoor activities. The region's natural beauty comes alive, making it perfect for exploring the area's scenic landscapes.
Early Fall (September - October)
With pleasant temperatures and fewer crowds, early fall offers a peaceful escape. This season showcases the area's vibrant colors and ideal conditions for outdoor adventures.
Off-Season Highlights
Mid Winter (January - February)
During this quieter period, you are likely to find more availability and better rates. The cooler weather creates a cozy atmosphere perfect for relaxing indoors or enjoying calm surroundings.
Late Fall (November - December)
The region experiences a decline in visitors, offering a tranquil setting. Cooler temperatures and holiday preparations make it an ideal time for those seeking a peaceful retreat.
Weekly Weather Forecast for St. Mary's County
How to Book Your St. Mary's County Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in St. Mary's County
Common Vacation Rentals Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor space with spacious lawns or gardens perfect for relaxing or outdoor activities
- Make the most of sunny days with access to a swimming pool or hot tub in the area’s vacation rentals
- Experience outdoor dining with patios, decks, or barbecue grills available at many properties
- Take advantage of scenic views from balconies or verandas overlooking the region's natural beauty
- Explore well-maintained outdoor fire pits ideal for social gatherings or cozy evenings under the stars
- Utilize nearby outdoor recreational facilities such as tennis courts or playgrounds often included with rentals
- Discover opportunities for boating, kayaking, or fishing right from your property’s waterfront access if available
Top Attractions Around St. Mary's County
What attractions are nearby?
During your stay, you can enjoy a variety of outdoor activities such as boating, fishing, and exploring scenic parks that showcase the natural beauty of this destination in St. Mary's County, Maryland.

Family Activities
- St. Mary's County Maritime Museum: Engage your family with interactive exhibits and maritime history at this educational museum, perfect for exploring local seafaring traditions.
- St. Mary’s River State Park: Enjoy a day of outdoor adventure with picnicking, hiking, and water activities along the scenic shores of the river in this picturesque park.
- The Patuxent River Naval Air Museum: Discover aviation history through engaging displays and aircraft exhibits at this family-friendly museum in the heart of the region.
- St. Mary's County Historic District: Take a step back in time exploring historic landmarks and charming streets that offer insights into the area's rich heritage, ideal for family outings.
Adult Activities
- Wine Tasting Tours: Explore local wineries and savor Maryland’s renowned wines while enjoying the scenic countryside here.
- Fishing Experiences: Cast your line on the region's waterways, where you can catch a variety of freshwater and saltwater species suitable for all skill levels.
- Historic Naval Ship Tours: Visit maritime museums and historical ships that highlight the area's rich naval history and offer engaging guided tours.
- Golfing Adventures: Play a round at one of the area's well-maintained golf courses, perfect for relaxing and challenging yourself amidst beautiful surroundings.
Other Places to Stay in St. Mary's County, MD
St. Mary's County Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Check the area's event calendar to align your stay with festivals or activities that showcase the region's unique culture and attractions.
- Explore Outdoor Activities: Take advantage of the natural beauty surrounding your rental by engaging in water-based pursuits or scenic hikes that highlight the destination's landscapes.
- Discover Local Cuisine: Visit nearby eateries or markets to enjoy authentic regional dishes that give you a taste of the area's culinary traditions.
- Prioritize Convenience and Comfort: Choose a vacation rental that offers easy access to key sites and amenities, ensuring a relaxing and hassle-free experience during your stay.
Transportation Options
- Personal Vehicles: Exploring the area by car offers flexibility and convenience, making it easy to access all the scenic spots and amenities nearby your vacation rental.
- Local Taxi Services: Reliable taxi providers serve this destination well, providing quick transportation options for daily outings or airport transfers within the region.
- Public Transit: The local bus systems connect key locations around here, allowing you to travel affordably without the need for a private vehicle.
- Rental Bicycles and Scooters: Enjoy an active way to explore the surroundings by renting bicycles or scooters, especially in areas with scenic trails and waterfront pathways.
Local Customs Options
- Crabbing Etiquette: When enjoying the local waterways, it's customary to observe specific crabbing practices, such as using proper gear and respecting size limits, which reflect the area's rich maritime traditions.
- Cultural Celebrations: Participating in regional festivals and events highlights the community's heritage, offering you a chance to experience authentic local customs firsthand.
- Historical Respect: Showing reverence for the area's historical sites and landmarks demonstrates an appreciation for the region’s storied past and cultural significance.
- Fishing Traditions: Engaging in or observing traditional fishing methods is a valued custom here, embodying the deep-rooted connection the community has with its natural surroundings.
Frequently Asked Questions About St. Mary's County?
1. What are the top vacation rentals in St. Mary's County?
There are a lot of options in St. Mary's County. If you plan on staying in the St. Mary's County area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in St. Mary's County:
- FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS
- A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
- 𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻 𝐇𝐀𝐘𝐒 𝐁𝐄𝐀𝐂𝐇 step of your porch into the sand 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘
- Piney Point, private , Beach Front Cottage
- 1.5 hours from D.C. - No Bay Bridge - Indoor Pool - Private Beach - Sunsets
- Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
- Waterfront Scotland Beach Retreat w/Private Beach
- El Camino
- Waterfront Getaway-Beach, Canoe and Boat Dock!
- Breton Bay Family Getaway
2. How many vacation rentals have private pools in St. Mary's County?
There are 1 vacation rentals with private pools near St. Mary's County. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in St. Mary's County are best for families?
If you are looking for a family-friendly vacation home in St. Mary's County, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in St. Mary's County:
4. How many Rentbyowner vacation rentals are available in St. Mary's County?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 162 in the St. Mary's County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in St. Mary's County.
5. What is the cancellation policy for vacation rentals in this area?
6. How do I confirm my booking for a vacation rental near here?
7. Are there any additional fees I should be aware of when booking a vacation rental in this region?
8. What amenities are usually included with vacation rentals in this destination?
9. Can I modify or cancel my reservation if my plans change?
St. Mary's County Top Rated Vacation Rentals
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