House holiday rentals in Southern Maryland

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

Custom waterfront home with everything you need to relax and recharge. Two levels of decks offer amazing views of the changing tides on Cat Creek. Soak in the hot tub and watch the eagles soar by, or head down to the dock for crabbing, fishing, and kayaking during high tide. Located in historic Southern Maryland, this quiet, hidden estuary makes for a unique getaway with great amenities. Fast WiFi for work, game room for fun, and a fenced-in yard for dogs. 1 hour from DC but feels worlds away.

Waterfront 4-BR home w/ hot tub & charging station

Immaculately maintained 4-bedroom waterfront home + home gym on Cobb Island with water views from every window! Four beach cruiser bikes & private dock w/ 4 kayaks, to enjoy the peaceful Neale Sound. Hot tub + private deck off of the kitchen. Wall of windows inside the home, flooded w/ natural sunlight. Views of the sound & the river side of the island. 3 BR are large (2 King beds/1 Queen), w/ their own BA (1 BR w/ BA is on 1st floor, no stairs). Smart TV's in 3 BR's. Great entertaining space!

The River House, a Wicomico Beach Retreat

Located right on the water of the Wicomico River with a private sandy beach, The River House will become your favorite retreat! This 5 bdrm, 3 bath fully stocked home has all the convenience of modern construction (including wifi) but maintains the vintage charm of the original property. The acre+ plot is very private with spectacular forest & water views. Fun can be found in every direction and for all ages! It has two bottom floor bed/bath combos, plus a fabulous sleeping loft for the kids!

Waterfront with sweeping bay view & private beach

Year-round private beach oasis on Chesapeake Bay! Perfect Fall & Winter Escape. An hour from DC beltway & world away. Recharge & relax to the sound of waves & sailboats. Spacious & fully renovated, with modern features, ample outdoor terraces. Enjoy long walks, nature spotting (bald eagles, rays, dolphins), shark tooth collecting. Kayaks provided! Short drive to Solomons Island, and local amenities: restaurants, bars, store, national parks & vineyards. No parties or events. Only relaxing.

The Little House on Back Creek

Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

*Solitude At Sunset*

YOUR WATERFRONT OASIS AWAITS! If you are looking for a true getaway, look no further. Tucked away on a small, peaceful island, this hidden gem is uniquely surrounded by 3 bodies of water: The Potomac River, the Wicomico River, and Neale Sound. This quiet island oasis offers the perfect place to step away from the busy world! This cottage is incredibly special to us. For four generations, it has been a sanctuary for our family-filled with love, laughter, and countless memories.

Waterfront home, private dock

Relax right next to the water in this tranquil Montross getaway. Fish, crab, kayak, paddleboard, or just sit on the swing and watch dolphins, eagles, herons, and stingrays from your private dock. Dine outdoors on the spacious deck, spend some some quality family time with an in-ground trampoline, tree swing, cornhole, bocce ball, spikeball, and a unique custom-built treehouse. Or just stay inside, relax, and enjoy the views, with an indoor electric fireplace and jacuzzi bathtub.

Waterfront Home: Osprey Getaway

Welcome to The Osprey Getaway! This spacious home is the perfect destination for families seeking a relaxing retreat. Our home is not far from Solomon’s Island, Patuxent River Naval Air Station, St. Mary’s College of Maryland, and historic Leonardtown. Here you'll find an open floor plan and plenty of space to unwind and take in your surroundings. Enjoy the peace and quiet of Cuckold Creek and the beauty of our newly renovated home. We can't wait to share our home with you!

Peace Point - Waterfront, Secluded, Home w/hot tub

Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

Potomac River Getaway

Discover an incredible escape at our cliffside gem on the Potomac! This 3BR, 2.5BA retreat has airy living spaces and panoramic river vistas from the wraparound deck. Enjoy your coffee as eagles soar above, and unwind in a private hot tub beneath star-filled skies, all while soaking in breathtaking riverside sunsets. Perfect for family and friend getaways, with historical sites close by. Montross’s small-town charm awaits your exploration—enjoy!

Water's Edge Cottage | Luxury Retreat

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”).

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).