Holiday rentals in Sandy Point

Waterfront Retreat | Sunset Views (Pet friendly)

Welcome to your tranquil getaway! This 2-BR, 2-BA home offers the perfect mix of outdoor relaxation and modern comfort. With a cozy coastal vibe, and a front-row seat to stunning sunsets over the Potomac, this retreat is ideal for anyone seeking a peaceful escape. Unwind on the covered deck or relax and enjoy the hammock & fire pit. You are close to many popular attractions e.g. Leonardtown wharf (13 miles), for fun water sports and activities, St. Mary’s College (23 miles), restaurants, etc.

Charming Waterfront Cottage with Sunset Views

Nestled on the Potomac River is "Pine Needle Nest." This 100-year-old pristinely redesigned cottage is the epitome of relaxation & waterfront living. Explore on bikes & kayaks or simply enjoy nature under the 100' pine trees. Oyster tastings, charter fishing & antiquing make this place perfect for travelers looking for the local vibe. Watch the sunset from any of the designer bedrooms, stylish kitchen, 90' pier or cozy firepit. Create nostalgic memories & experiences that will last a lifetime.

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.

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

Living on Island Time

Relax with the whole family and spend life on Island Time. Full bar set up with ice maker and wine refrigerator. Private pier, paddle boards and firepit. Unwind on St Goerge Island or head out to one of the local eateries for some southern Maryland faire. Inside you have 2 spacious rooms, 2 bathrooms. A massive island for cooking, card playing or just great conversations with endless views. Crabbing, fishing. The Neighbors have 2 Great Danes and a cat that you may see occasionally

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.

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.

River + Beach Front Cottage 4 BR ADA Northern Neck

Captain Davis Cottage is a waterfront retreat on the Northern Neck ( Sandy Point, Virginia) near where the Potomac River meets the Chesapeake Bay. Enjoy a large private beach + pier for relaxing, fishing, and taking in the views. Includes main cottage (3BR/2BA), guest cottage "The Brig" (1BR, no bath), ideal for families or groups. ADA-friendly. 3-night min. for Mem Day + Labor Day weekends. Summer stays run Friday to Fri. Message for shorter stays.

Good Vibe Villa, Tiny houseboat

This tiny houseboat sits permanently on a boat lift, so you will have the unique experience of being over water without the risk of sea sickness! Located in the heart of quaint Solomons Island, this is a great stay if you love being near the water. Unparalleled views from your private porch. Please note, due to extensive pet damage we have changed this property to strictly no animals. You will be asked to leave if you arrive with a pet.

Waterfront Cottage on the Potomac River

Escape to our serene waterfront cottage on the Potomac River, just 2 hours from Washington D. C. and the Richmond area. This retreat comfortably sleeps 5 and features a private pier for fishing, a sandy beach for relaxing, cozy sun room for reading, and breathtaking water views. Enjoy a fully stocked kitchen, fast WiFi, and a spacious deck. The perfect spot for a romantic weekend, a special celebration or a simple peaceful retreat.

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”).

Osprey Landing - Peaceful Waterfront home and Dock

Relaxing waterfront home with private pier surrounded by water on two sides. Relax and enjoy the peacefulness of the view and serenity of Cralle Cove just off the mouth of the Potomac river and Chesapeake Bay. Watch the ospreys and eagles fly about in their natural habitat. Sit or eat on either the covered or uncovered decks. Enjoy quiet evenings around the fire pit.