Holiday 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.

Historic Rousby Hall, Waterfront, Pool, Beach

*Heated pool open to Nov 2* Rousby Hall is a stunning 5-star 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 (May–October) with amazing river views. The estate also hosts weddings and events for up to 100 guests (additional event fee applies).

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!

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.

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.

Secluded Pool Oasis Whole house 5 bedrooms 6 beds

ALERT POOL CLOSED FOR THE SEASON SEPTEMBER 27. 25 thru April 1, 2026. Escape to this secluded cul-de-sac retreat with 5 spacious bedrooms, TVs with streaming, and a 10-ft deep pool with diving board and floaties. Relax on the stylish patio or porch, enjoy outdoor TV viewing, and explore over an acre of yard space for games or inflatables. Perfect for families or friends—fun, comfort, and unforgettable memories await.

Clearview | an ESVR property

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. Talbot County STR License STRN-22-1