Holiday rentals with a pool in Calvert County

Tranquility on Tilghman Island – Wide Water Views

Wake up to sweeping waterfront views, spend your days crabbing from your private dock, kayaking along the shore, or lounging by the pool with a good book. Just minutes from charming St. Michaels, this 4-bedroom retreat blends coastal charm with modern comfort — perfect for families, friends, or a romantic getaway. In the evenings, grill, gather around the firepit under the stars, and let the day fade away in the bubbling hot tub. Guests love the spacious layout, the dreamy screened-in porch for

Family · Location · Condition

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

Location · Family · Nearby

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.

Family · Location · Pool

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 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.

Family · Value · Beach

Grand Tudor Home w/ Saltwater Pool & Hot Tub

Welcome to our Grand Tudor Home, a peaceful retreat where families and friends can relax, reconnect, and create lasting memories. Nestled on 3 acres, this elegant 5-bedroom, 3.5-bath home offers approximately 4,700 sq ft of beautifully designed living space with a private saltwater pool (June–September), year-round hot tub, gourmet kitchen, and spacious gathering areas. Minutes from Chesapeake & North Beach, easy driving distance to Solomons Island, Annapolis, and Washington, DC.

Family · Location · Cleanliness

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).

Location · Family · Beach

Maryland Vacation Rental w/ Private Pool & Dock

Adventures await at this 4-bedroom, 2-bathroom Lusby, MD, vacation rental! This waterfront home features a private dock, pool, and deck for a serene view of St. Leonard Creek. Take the paddleboards out on St. Leonard Creek or have fun at Calvert Cliffs State Park. While you’re there, relax on the sandy beach with the family. Come back to this home away from home and eat at the outdoor dining area. After dinner, gather around the Smart TV to watch your favorite movie.

Family · Location · Decor

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!

Value · Family · Accuracy

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).

Family · Location · Heating

Studio on the Bay.

This studio apartment is in walking or driving distance to three private beaches in our community. There is 1 bedroom with a queen size bed, spacious bathroom and closet. The living room has a pull out full size bed and a kitchenette. Coffee, teas, beach chairs, are provided. Wanna fish??? Ask Joey about Fish Taxi! Fifteen minutes from Solomons Island (home of the Tiki Bar). An hour or so from DC, Annapolis and Waldorf.

Value · Family · Heating

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!

Family · Location · Hospitality

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

Location · Comfort