Holiday rentals in Sandy Point

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Top-rated holiday rentals in Sandy Point

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Guest favourite
Home in Piney Point
4.89 out of 5 average rating, 9 reviews

Cove Cottage

**Welcome to Cove Cottage!** Escape to our charming cottage on the tranquil shores of Piney Point Waters. Enjoy stunning views and the soothing sounds of nature in this unique retreat, perfect for couples, families, or solo travelers. Our cozy space features modern amenities (sauna, hot tub, fire-pit, Wi-Fi, arcade, and kayaks). Spend your days exploring nearby trails on our bicycles or relaxing on the deck swings. Book your stay today and discover the ideal spot to unwind in nature’s beauty!

Top guest favourite
Cottage in Leonardtown
4.96 out of 5 average rating, 262 reviews

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.

Top guest favourite
A single-story house is shown with blue siding and white trim, featuring a prominent brick chimney and a welcoming pink door. Large windows provide ample natural light. A grassy area surrounds the home, with trees adding greenery in the background.
Home in Piney Point
5 out of 5 average rating, 160 reviews

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

Top guest favourite
A serene view of the St. Mary's River is framed by a white awning. Calm waters reflect the clear blue sky and a single sailboat is visible in the distance. Lush greenery lines the far shore, enhancing the peaceful atmosphere.
Flat in Lexington Park
5 out of 5 average rating, 405 reviews

Adorable Waterfront Apt Weekend Getaway & Scones!

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here year around! SUNSETS! Enjoy our Homemade SCONES too!!

Guest favourite
Aerial view of a spacious house surrounded by lush greenery, with a private pier extending into the water. The house features a large, wrap-around porch and several trees dotting the landscape, creating a natural and serene setting by the water.
Home in Scotland
4.89 out of 5 average rating, 163 reviews

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.

Guest favourite
A wooden pier extends over calm waters, leading to a modest rural home with a prominent deck. A child is seen crouching on the pier, engaged in a quiet activity. Lush greenery and distant trees frame the scene, contributing to the tranquil atmosphere.
Home in Piney Point
4.78 out of 5 average rating, 59 reviews

Waterfront island retreat

Relax at this modest, tranquil getaway on St George Island. Experience protected areas of the Potomac River and St Mary's River shore. Watch turtles, fish, crab, otter, and birds from the 100-foot pier and decks. Enjoy the picnic table on the shoreline with colorful sunsets. High tides carry debris onshore and across yards a few times yearly. Stay aware of the unique environment with sea nettle jellyfish in July and August, and mosquitos from the marsh in warm months.

Top guest favourite
A scenic view of a sunset over the water, with a silhouette of a person kayaking. Adjacent, a cozy seating area is set up around a fire pit, surrounded by trees. In the foreground, a table with wine and glasses is shaded by a red umbrella, beside a hot tub.
Home in Dameron
4.99 out of 5 average rating, 136 reviews

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.

Top guest favourite
The exterior of the cottage is showcased, featuring a charming green facade with white trim. A spacious front porch with large windows invites guests to enjoy the surrounding landscape. A large tree is visible above the cottage, enhancing the picturesque setting.
Cottage in Kinsale
4.98 out of 5 average rating, 43 reviews

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.

Top guest favourite
Cottage in Hague
4.99 out of 5 average rating, 207 reviews

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.

Top guest favourite
A spacious open-concept living area features large windows offering unobstructed views of the water and sunset. A comfortable sectional sofa is positioned near the windows, with a dining table visible in the background. Natural light fills the space, enhancing the tranquil setting.
Home in Leonardtown
4.99 out of 5 average rating, 134 reviews

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”).

Guest favourite
A private pier extends into calm water, providing space for relaxation and fishing. A waterfront home is situated behind the pier, framed by greenery. The serene surroundings and gentle ripples in the water highlight a tranquil atmosphere.
Home in Lottsburg
4.98 out of 5 average rating, 139 reviews

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.

Guest favourite
The cottage is framed by a large flowering tree and surrounded by lush greenery. A spacious screened porch is visible in front, providing a cozy outdoor space. Daffodils bloom in the foreground, enhancing the rural setting on a peaceful landscape.
Cottage in Lottsburg
4.91 out of 5 average rating, 116 reviews

Charming Waterfront Home with Expansive Views

Mom and Pop's Honest Point Home has been in our family for almost 70 years. It has been and continues to be a haven for anyone seeking a relaxing rural property. The cottage is situated on many acres surrounded by water, farmland and wildlife. Your only neighbor is the owner's home which is next door. Make sure you read the details below

Popular amenities for Sandy Point holiday rentals