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

Location · Family · Amenities

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 · Layout

Clearview | an ESVR property

Big Amenities: Pool Hot Tub Amazing Views! Clearview is the answer to your getaway needs. With a swimming pool, hot tub, and views that go on and on, you can stake your claim to this spot and relax throughout your stay! Those who want to venture out can mingle with the Tilghman Island locals, watch the fresh catch come in straight from the Bay, or enjoy a sunset cruise from nearby Dockside Express. Gourmet dinners at one of the local restaurants or a day trip into St. Michaels will have the

Family · Location · Cleanliness

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.

Location · Family · Indoor spaces

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.

Location · Value · Outdoor spaces

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 · Nearby

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.

Family · Location · Check-in

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!

Location · Family · Pool

Private Pool + Spa Retreat | Maryland Crab Feasts

Welcome to your private Southern Maryland retreat, where pool days, Maryland crab feasts, wedding weekends, and family gatherings come together. Relax by the pool and spa, gather around the fire pit, fire up the grill, or enjoy a Crab Feast. Minutes from Solomons Island, Calvert County wedding venues, Calvert Cliffs, and nearby military installations. Note to guests from the city: The house is located in the country there are pests and bugs.

Location · Value · Bathroom

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).

Location · Family · Wifi

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 · Location · Accuracy

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!

Location · Family · Beach