Vacation 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

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

Historic Rousby Hall, Waterfront, Pool, Beach

**Heated pool open to Nov 2. Thanksgiving chef dinner options** 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 with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee additional).

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.

Waterfront, pool, pickleball

Escape to this luxurious two-story waterfront home with two master suites, sleeping up to 12. Enjoy a gorgeous 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!

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), covered 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

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.

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, two corn hole game sets, 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!

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.

Pool Oasis Upstairs Suite

ALERT POOL CLOSED FOR THE SEASON SEPTEMBER 27. 25 thru April 1, 2026. Bright and spacious 3BR, 2-bath upstairs suite perfect for families or groups. Features a master bedroom with king bed, two additional bedrooms, full kitchen, dining area, and cozy living room. Enjoy shared access to a 10-ft deep pool, firepit, grills, patio, and large yard. Ideal for comfort, convenience, and making lasting memories indoors and out!