Holiday houses in St. Mary's County

Rolling Stone Farm - Charming 1930s House

Rolling Stone Farmhouse, a charming 1930’s home lovingly restored. Conveniently located within 5 miles of Patuxent River Naval Air Station, and 2 miles to St. Mary’s College of Maryland. Located on a farm with sweeping views of the fields and ponds, with an English garden right beside the back porch. Private, quiet, relaxing but within 10 minutes of shopping and restaurants. During your stay, the house and yard are dedicated to just you and your guests. Ask about the adjacent studio apartment.

Heron Cove

Take it easy at this unique and tranquil getaway. Enjoy Heron Cove on the Patuxent River in Southern Maryland. The sunrises are breathtaking. Enjoy eagles and herons feeding in the pond. Sit on the patio and enjoy the view,the fire table or kayaking in the inlet. This lovely apartment is located 5 min.from Pax River Naval Air Station, 20 min. from St Mary’s College, near many historical sites, and 10 min. from the quaint village of Solomon’s Island. It is also located near 20+ restaurants.

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.

Serene setting great location surrounded by woods

The one-bedroom apartment will sleep 2 adults and 1 child under 18. In a serene setting with woods, a fish pond, and a comfortable patio. Separate code lock entrance. Well-equipped kitchen. Free WiFi, two TVs with Netflix and Amazon Prime. There is also a cedar sauna. Parking is on the property. Apartment situated near shops, restaurants, St. Mary's College and the Patuxent River Naval Air Station. 15 minutes from Chesapeake Bay, 1 hour to DC beltway. French and German also spoken.

Old World Cottage/Fabulous Sunsets/Polite Pets OK

Immaculate cottage with old world detail and large stone patio. Easement to water to enjoy the fantastic Southern Maryland sunsets dipping beyond the Potomac River. Situated in St Mary’s County near Piney Point and St George’s Island. A short walk to Tall Timbers Marina. Boats and polite pets are welcome with prior approval. Central heat & air conditioning, Front-yard fire-pit, Fast Internet, Smart TVs, Cable 2 Plastic Kayaks Fully stocked Kitchen, and bedding Crab net Fish Table

White Point Cottage -- Quiet Waterfront Getaway

Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. More on IG @whitepointcottage, and be sure to visit our sister property, Water's Edge Cottage.

Walk to famous Tiki Bar on Solomons Island!

Cute studio apartment on charming Solomons Island. Walking distance to restaurants, live music, boat and kayak rentals. The kitchen has a full sized refrigerator, microwave, toaster, two burner hot plate and coffee maker. We provide all bedding and bath towels for two people. Enjoy your coffee ( provided) or wine on the deck in the fenced in side yard. One well-behaved pet is welcome. Please make sure you pay the pet fee. We also have a boat slip across the street that you can rent

Spacious Gorgeous Waterfront Home with Sunset View

Dreamy weekends on the water, the perfect getaway for the entire family and friends in the southern tip of St Mary’s peninsula. This gorgeous newly remodeled house with 5 Bedroom 3.5 Bath sleeps 10 very comfortably. Wake up with amazing water views and access to the water with your own private pier. Spend your day crabbing, fishing, kayaking, or paddle boarding. Amazing beaches at Point Lookout State Park, just a few minutes away. High speed internet, WiFi, and cable.

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.