Vacation rentals with a pool in St. Mary&#x27;s County

4.89 out of 5 average rating, 56 reviews

Aerial view of a home with a fenced swimming pool, surrounded by lush green grass. The pool features a clear blue water, and several lounge chairs are positioned around its edge. Steps lead from the house to the outdoor area, enhancing accessibility to the pool.

Home in Ridge

Waterfront Paradise with a Private Pool

Set on three acres of spectacular waterfront property, there’s everything you need to escape – a dock, a fire pit, crab traps, kayaks, bikes and a POOL. Next door: 20 acres of unkempt forest where bald eagles fly. The pool is closed until end of April and is not heated. The home is warm, unpretentious, with a minimalist approach to décor but a stocked kitchen for those who love to cook. Amenities: a HDTV with premium channels, high speed internet, a ping pong table, lawn croquet and more.

4.92 out of 5 average rating, 79 reviews

A private salt-water pool is featured, surrounded by lush greenery. The pool's shimmering blue water reflects the sunlight, while a smooth entry step leads into the inviting space. A safety fence encloses the area, ensuring guest privacy.

Home in Lusby

Spacious and private waterfront, sleeps 10

Are you looking for a family getaway or a peaceful location to telework? This property offers it all. Tastefully remodeled waterfront property with a large private salt water pool, dock for fishing, crabbing and kayaking. One-floor open plan with two large decks. Great for entertainment in privacy and is in proximity to restaurants, vineyards, beautiful beaches and parks of Chesapeake Bay and Patuxent River. Just 1 hour to the south of Washington DC and within minutes to NavAir base and Excelon

A lone swan glides across calm water, creating gentle ripples. The bird's white feathers contrast against the soft blue of the lake. Surrounding the swan, large, round stones edge the water's surface, providing a natural border to the serene scene.

5 out of 5 average rating, 13 reviews

Water View Cozy Getaway- beach/Kayak/fishing/pool

Welcome to your ultimate waterfront community getaway! Our charming and cozy house is newly built 4 bedrooms and 4.5 bathrooms and 3 minutes Walking distance to the public beach, making it the perfect retreat for anyone looking to enjoy modern amenities in a serene and tranquil setting. Whether you're looking for a romantic getaway, a family vacation, or a peaceful retreat, our house offers a truly unique and unforgettable experience. We can't wait to welcome you to your home away from home!

4.99 out of 5 average rating, 150 reviews

Beach Please! River cottage w/private beach & dock

Come unwind at "Beach, Please!" Our renovated cottage on the river with a private beach and dock is waiting for you! What's there to do? There's boating, fishing, crabbing, bird watching, tanning, and hammock-napping. Need more? Ok, antique shops, breweries, wineries, live music, crab boils and oyster fests. Still need more? Cornhole, can jam, horseshoes, hiking, and swimming and tennis at the community pool. That's not all, so just trust us - you will LOVE your time in Montross, Virginia!

A serene sunset view over the Potomac River is captured, with gentle reflections shimmering on the water's surface. Silhouette of tall grasses frame the image in the foreground, while silhouettes of docks are visible along the shoreline.

4.93 out of 5 average rating, 46 reviews

Brigadoon, the BRAND NEW Waterfront Haven

Relax with your whole family at our peaceful home. Discover an oasis of serenity at this stunning 3-bedroom, 2.5-bath retreat boasting panoramic views of the Potomac River from every window. Marvel at breathtaking sunrises and sunsets, from your own private beach, immersing yourself in the tranquility of the landscape. Situated just 2-3 hours from the Washington, DC Metro Area, 2 hours from Charlottesville, and 1 hour from Richmond, this haven offers an easy escape into nature's embrace.

An aerial view of the house showcases a spacious deck with comfortable seating, surrounded by a railing. A dock extends into the water, equipped with a covered boat lift. Lush greenery borders the property, providing a serene backdrop.

4.97 out of 5 average rating, 87 reviews

Waterfront Gem: Dock, Hot Tub, Beach, Pool, Kayaks

Welcome to the Rivah! Lovely and inviting freshly renovated and beautifully decorated house with 5 bedrooms and 3 full bathrooms. Relax on the covered porch, large double deck with new hot tub, or our private dock. Walk the private beach and look for bald eagles, gaze at an evening fire, go crabbing/fishing, or jump in the community pool! Bring your boat + jet skis! We provide two kayaks and two standup paddle boards. There are two private community beaches in the neighborhood to enjoy!

Superhost

A private, fenced-in pool area is shown, featuring a clear blue pool surrounded by a spacious patio. Lounge chairs are set around the pool, and a covered seating area is visible nearby, providing options for relaxation in a tranquil outdoor setting.

Cottage in Heathsville

4.83 out of 5 average rating, 75 reviews

Riverfront Retreat with PRIVATE POOL and BEACH!!

Welcome to your riverfront retreat. Only a 2 hour drive from DC/RVA, this riverfront cottage has everything you need to get away. After spending time on your private beach, relax in your own pool, before spending the evening relaxing in the screened in porch or by the firepit. Sunny? Take out the kayaks, stand up paddle boards or cornhole. Rainy? The home is furnished with TVs, chromecasts, high speed internet, board games and puzzles. Follow us on IG @riverfront_retreat for more

5 out of 5 average rating, 15 reviews

The backyard features a private pool surrounded by landscaped gardens and a variety of seating areas. Flowering plants add color to the foreground, while lounge chairs line the poolside. The house and trees are visible in the background, complementing the serene setting.

Home in Lusby

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

Welcome to our waterfront paradise overlooking the Chesapeake Bay! Experience comfort and tranquility at this extraordinary retreat, where breathtaking views and unforgettable memories await you. This serene beachfront property is little over an hour from DC & Northern Virginia, and about 90 minutes from Baltimore. With private pool, fire pit, kayaks, paddle boards, pingpong, weights & workout equipment, it's a perfect place to recharge and make memories with family and friends.

4.93 out of 5 average rating, 200 reviews

The Glebe

This 3br 2ba home with own private beach is nestled off of the Potomac River and boasts serene and expansive views. Sunbathe on the private beach, cool off in the water, go fishing/crabbing from the dock, or just listen to the waves crash. Whatever it is, you’ll find it absolutely relaxing. Be sure to explore local wineries, breweries, shops and enjoy the community pool and tennis court. It's the perfect getaway house for couples/families or anyone looking for a serene weekend.

Superhost

A serene view of a private beach meets the calm waters of the bay under a clear blue sky. Gentle waves lap at the sandy shore, with a wooden dock extending into the water. Soft grasses frame the beach area, contributing to the tranquil atmosphere.

Villa in Montross

4.85 out of 5 average rating, 95 reviews

Beach Retreat

Relax with the whole family at the Beach Retreat! Enjoy the beautiful Sunrise and Sunsets in the Hot tub overlooking your own private beach! There is plenty to do in the Northern Neck of Virginia! We have Wineries, a Brewery, historical sites, boating, swimming, fires on the beach, bike rides, kayaking, plenty of Summer and Fall Festivals and so many great places to eat on and off the river! The Northern Neck of VA is a hidden gem! Just a 90 minute drive from the DC area

5 out of 5 average rating, 138 reviews

A serene poolside area is framed by lush greenery and a large tree, providing a peaceful view of the water. Lounge chairs are positioned for relaxation, with picnic tables nearby. The clear blue sky and calm water create a tranquil atmosphere.

Home in Lusby

Historic Rousby Hall, Waterfront, Patuxent River

“SUMMER July 11-Aug 1 is a one-week minimum, Friday to Friday” Rousby Hall is located on the Patuxent River, outside of Solomons Island with a view of the river's opening to the Chesapeake Bay. The 16-acre property is adjacent to our very private conservation area that borders our 300-foot private beach. The year-round property has a pier, and in-ground pool (May-October) with amazing river views. Also hosts weddings+events up to 100 guests.