Visit St. Mary's County Maryland

Where the Potomac & the Chesapeake meet

Vacation Rentals

Want to relax at a place all to yourself? Here are some great properties choose from - try a fishing lodge, a beach house on the Chesapeake, or other fun vacation rentals.

Chesabelle Beach House

Lake Drive, Scotland, MD 20687

38.08332 -76.33244

(571) 217-3659

Chesabelle is a fully renovated, 3 bedroom, two bathroom beach house is with stunning views across a small estuary into the Bay. The house is equipped…

Chesapeake Charm

50176 Dove Cove Road, Dameron, MD 20628

38.13397 -76.34121

(301) 904-0935

This waterside Cottage Living style home provides an excellent get-away weekend or summer retreat. Kayak, crab, fish, bbq, soak up gorgeous sunsets or just sit back…

Colton’s Point Studio & Artist’s Retreat

20259 Colton's Point Road, Coltons Point, MD 20626

38.22493 -76.75397

(301) 769-3273

Retreat to "Where Maryland First Began" in 1634. A detached one bedroom apartment with a fully equipped kitchen. Next to an artist's studio where guests can…

Colton’s Shipping Point Farm Cottage

39244 Burch Road, Avenue, MD 20609

38.26539 -76.71947

(301) 807-0988

This 130 acre tree farm along the shore of St. Clements Bay has been family owned since 1888. This two bedroom cottage is perfect for a…

Hess House Vacation Rental

17342 Piney Point Road, Piney Point, MD 20674

38.14404 -76.5092

(301) 994-0111

Built in 1915 and lovingly restored by the current owner, Hess House offers two bedrooms (full beds) with two full baths along with areas for reading…

Island Estate

PO Box 333, St. George Island, MD 20674

38.11485 -76.4794

(410) 456-0572

Located on the shores of historic St. George Island (est.1638), this 6,500 sq. ft. custom-built home is situated on 6+ wooded acres with expansive views of…

Kentigern Beach House

Lake Drive, Scotland, MD 20687

38.08373 -76.33145

(571) 217-3659

Enjoy lovely Chesapeake views from this private beach house. The four-story house offers outdoor luxury living in beautiful South County. Surrounded by glass and balconies on…

Piney Point House on St. George Island

16300 Thomas Road, Piney Point, MD 20674

38.11594 -76.47909

(703) 350-5530

Experience luxury, peace, and tranquility when you stay at this superb 4-bedroom, 2.5-bathroom vacation rental house that sleeps 12 lucky guests on St. George Island with…

Summerlee Beach House

Lake Drive, Scotland, MD 20687

38.08626 -76.33152

(571) 217-3659

Bring the family to this classic 5 bedroom, 5 bathroom beach house, which has been fully renovated and newly furnished. Situated directly on Chesapeake, hear the…

T-House Cottage

24038 North Patuxent Beach Road, California, MD 20619

38.32142 -76.47920

(240) 315-4844

This cozy cottage is a 704 square foot vacation rental that has been completely remodeled. The floorplan was updated to an open concept kitchen, living, and dining…

Tall Timbers Cottage

18358 River Road, Tall Timbers, MD 20690

38.17196 -76.54518

(240) 460-3903

Two hours from DC you will find a fabulously renovated Tall Timbers Cottage with beautiful interiors, nice woodland views and cozy central heat, two electric fireplaces…

The Hideaway on Hays Beach

Holly Drive, Scotland, MD 20687

38.09133 -76.3323

(301) 250-8384

The Hideaway on Hays Beach is the perfect getaway for singles, couple or families. From the front door, cross Holly Drive and you're only steps from the…

Visit St. Mary's MD
23115 Leonard Hall Dr.
P.O. Box 653
Leonardtown, MD 20650


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