Holiday rentals with a pool in Calvert County

Newly Renovated River Retreat w/Dock and Pool

Enjoy this newly renovated 4BR/3.5 bath home in a peaceful wooded setting on St. Leonard's Creek with an indoor pool and a large dock that's perfect for crabbing, fishing, canoeing, kayak, etc. Grill out and sit on the screened in porch, take a dip in the pool, or enjoy the game room that has two TVs, a bar, foosball, etc. Only 15 mins to Solomons Island's restaurants/boat tours & rentals, etc. and even closer Calvert Cliffs State Park for hiking & the beach. Enjoy nearby wineries and more!

Relax by the Water - Summer Dates Available!

STRN-24-62. Wonderful waterfront home. Minutes from St. Michaels offering all you'll need for the perfect vacation experience. Fabulous location with panoramic views of the water everywhere you look. Crab and fish from the dock. Hop on a bike and explore the island by land and then try out kayaks for a water adventure. Cool off with an afternoon dip in the pool. Enjoy starry nights at the waterfront firepit. If the bikes and kayaks wore you out relax your muscles in the hot tub. Perfect!

Luxury Farmette -Huntingtown MD -1hr to DC- Pool

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.

Indoor pool/spa nestled in Southern Md. woods.

Contemporary all-brick French manor nestled within 16-acres of secluded woodlands. Indoor pool/spa with waterfall inside a stunning, sunlit atrium. Three bedrooms and three bathrooms accommodate 6-8 people. Centrally located near the Chesapeake Bay where quaint towns include restaurants, antiques, sandy beaches and fishing boat rentals. Centrally located for trips in all directions: Washington, D.C. (35 miles); Annapolis (30 miles) Baltimore (50 miles) and Ocean City (139 miles).

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.

Waterfront, pool, pickleball

Escape to this luxurious two-story waterfront home with two master suites, sleeping up to 12. Enjoy a heated pool, large decks with scenic views, and a deep-water pier perfect for boating and fishing. Gather around the fire pit or stay active on the private pickleball and tennis court. Inside, spacious living areas offer comfort and style, ideal for families and groups. A serene retreat for relaxation and adventure alike. Book now for an unforgettable waterfront getaway!

Pool-side chickens between D.C. and Chesapeake Bay

Connect with family or friends at this peaceful two bedroom apartment with pool located in the DC metro area and minutes from Chesapeake Bay sports and fishing. You will enjoy the outdoors in comfort. 🏊💦 In-ground Pool 🔥🏕️ Fire pit 🔥🍔 Charcoal grill and picnic table poolside 🚙🚗 Free parking for up to two cars 🧑‍🧑‍🧒‍🧒🧑‍🧑‍🧒‍🧒 Private space for up to eight guests, including kids. 🐓🐥 Free Range Chickens Sightings

Waterfront Bliss: Ultimate Tilghman Retreat

ST-217-FLU Welcome to your dream waterfront getaway just moments away from the charming town of St. Michaels. This meticulously designed vacation home is tailored for the ultimate relaxation and adventure, offering a seamless blend of comfort, luxury, and outdoor excitement. Picture yourself returning from an exhilarating day on the Bay, gently mooring your boat to the private dock before plunging into the refreshing  pool.

Historic Rousby Hall, Waterfront, Pool, Beach

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 (additional event fee applies).