Vacation rentals with a pool in Calvert County

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

Luxury Farmette -Private & Secluded-1hr to DC

Plan your tranquil getaway to the countryside and escape to a luxury dream farmhouse. Located on 5 acres, the fully renovated home offers peace in a quiet, private location. Guests have access to a pool and outdoor shower, fire pit, a covered grilling area and a playground for children. The home is located approximately 1hr from Washington DC and is the perfect place for a retreat, family vacation and everything in between! Plenty of parking available for those traveling with boat/camper/RV.

Spacious Private Retreat on the Patuxent River

Perched at the point of 55 wooded acres with water on three sides, this modern complex is the epitome of outdoor living in peace and seclusion. Grill on the tip of the peninsula and soak in the views. Living room/kitchen areas are designed for gatherings, as are the twin 100 ft covered porches, while the dock leads to a stunning private cove. The annex provides a cozy retreat with two bedrooms, bathroom, kitchen/den and deck with water views. Lounge by the pool or take a dip to cool off.

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.

Fire pit, pool, and chickens between D.C. and bay

Connect with family, friends and nature at this quiet one bedroom, one den apartment located in the DC metro area and minutes from Chesapeake Bay sports and fishing. Enjoy the outdoors in comfort! 🏊💦 In-ground Pool (1st Sat. May-1st Sat. Oct) 🔥🏕️ Fire pit 🔥🍔 Charcoal grill and picnic table poolside 🎥🍿 Disney Plus 🚙🚗 Free parking for up to two cars 🧑‍🧑‍🧒‍🧒🧑‍🧑‍🧒‍🧒 Private space for up to eight guests, including kids. 🐓🐥 Free Ranging Chicken Sightings

Private Country Escape • Spa • Fire Pit

Welcome to your private country escape—a spacious, inviting home designed for gathering, relaxing, and creating memories. Nestled in a quiet and very private neighborhood, this 5-bedroom, 3.5-bathroom retreat offers over 4,500 square feet of comfortable living space for up to 10 guests. Whether you’re reconnecting with family, spending quality time with friends, or working remotely in peaceful surroundings, this home offers everything you need for a memorable stay.

Patuxent River View

🌊 Nestled near North Beach, Herrington Harbor, Herrington on the Bay, and Chesapeake Beach, this serene guest house offers a peaceful escape for travelers of all kinds—whether you’re exploring local sights, reconnecting with nature, visiting family, or just passing through. Guests enjoy thoughtful amenities at no extra cost: a fully stocked kitchen, complimentary coffee and tea, high-speed WiFi, a pool and gazebo, and more comforts to make you feel right at home.

Tudor House Oasis

Welcome to your secluded retreat—this elegant 4‑bedroom, 3.5‑bath estate offers approximately 4,700 sq ft of upscale living space set on nearly 3 acres. Features include a 40 x 20 saltwater pool(June-September), hot tub, home theater, gourmet kitchen, and refined designer finishes throughout. 🏖 Beach Access: Chesapeake Beach, MD – ~10 miles North Beach, MD – ~11 miles 🛥 Solomons Island & Other Attractions Annapolis – ~30 miles Washington, D.C. – ~39 miles

Stunning North Beach Getaway w/ Inground Pool

Indulge in this beautifully appointed 4-bedroom, 2-bathroom house 6 blocks from the Chesapeake Bay boardwalk! Revel in a chef's kitchen, open living area, screened porch, with separate workspace. Relax by the heated saltwater pool BBQ on the deck or gather around the cozy firepit. Walk to restaurants and enjoy live music experiences, the local wine bar or beer, conveniently close to local wedding venues. This North Beach gem guarantees an unforgettable stay!

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower, an outdoor redwood panoramic barrel sauna and a redwood cold plunge!

Bliss By The Bay Chalet

Relax and recharge at Bliss By The Bay Chalet. This cozy retreat is the perfect place to unwind. The coastal style will put you at ease. Relax with meals on the deck, enjoy your private 12 foot in-ground pool, or take advantage of either of the two private community beaches on the Chesapeake Bay or at the private Lake Lauriat. Historic Solomon’s Island is only four miles away! Everything you need to unwind is right here!

Waterfront Bliss | an ESVR property

Welcome to Waterfront Bliss, a private 4-bedroom, 3-bath waterfront retreat on Tilghman Island, Maryland. Enjoy stunning water views, an open living space, gourmet kitchen, and serene primary suite. Relax by the private pool, grill on the deck, or head out from your private, dock for boating, fishing, or kayaking. Minutes from marinas, seafood dining, St. Michaels, and Easton. Talbot County License: STRN 24-12