Holiday rentals in Piney Point

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

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.

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!

Waterfront New Piney Point A-Frame

Welcome to La Belle Vie! Cherish a unique waterfront getaway in our new chic A-frame, located in tranquil Piney Point where the St Mary's River meets the Chesapeake Bay. Revel in panoramic views, kayak, fish, catch crabs, birdwatch, float off the dock, or unwind on the deck. Inside, modern amenities blend with stylish charm for comfort. Nearby: nature trails, beach, restaurants, and boat ramp. Fun fact: Piney Point provided a nature retreat for Presidents Monroe, Pierce, and Teddy Roosevelt.

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.

Piney Point Harbor Haven

Welcome to your dream getaway in charming Piney Point, nestled in historic St. Mary’s County. This beautifully maintained 3-level waterfront home offers the perfect blend of serenity, luxury, and adventure, all in one unforgettable stay. Wake up to sweeping water views from nearly every room. This spacious retreat features a private pier, complete with a ladder, floating dock for jet skis—perfect for boating, kayaking, paddleboarding, crabbing, or just soaking in the peaceful surroundings!

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.

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 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.

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”).