Vacation rentals with a pool in Calvert County

Scientists Cliffs Fossil Beach Apt Hike over Cliff

WILD! This cabin apartment near the beach is the lower floor of my home. Bask, swim, kayak, bike or hike the American Chestnut trails or Cliffs stairs. Sailing evenings or weekends optional. Wifi from your apartment or in your double hammock or on deck. Beach, fossils, trails, lake, woodstove. Bring your fishing poles. Pool w baby pool. Enjoy your own grilled meals or hard crabs on my deck which seats 12. I can stock your fridge or order your steamed crabs upon request . 1 hr from DC or BWI.

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

The Hideaway on the Patuxent River

Nestled along the Patuxent River, this secluded hideaway offers the perfect family retreat, with river access just steps from your door. The swimming pool is is available on a reserved basis as it is shared with the hosts and is located behind the main house, approximately 100 feet from the guest house, offering convenient access during your stay. The pool is seasonal and open from Memorial day to Labor day. This is the escape you have been searching for and we look forward to welcoming you.

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

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!

Patuxent River View

🏡Stay at this peaceful, amenity‑rich guest house near North Beach, Chesapeake Beach, and Herrington Harbour, with quick access to Washington, DC, Baltimore, and Annapolis. Enjoy a fully stocked kitchen, coffee, fast WiFi, a seasonal pool, and a shaded gazebo designed for comfort and convenience. Perfect for wedding weekends, family visits, work trips, and quiet coastal getaways, this cozy home base makes it easy to relax, cook, stream, and recharge between festivities and exploring the area.

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.

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.

5BD Country Escape | Gym, Spa, Pool, & Fire Pit

Welcome to your private country escape—a spacious, inviting home designed for gathering, relaxing, and creating memories. Nestled in a quiet and very private neighborhood, this 5-bedroom, 3.5-bathroom retreat offers over 4,500 square feet of comfortable living space for up to 10 guests. Whether you’re reconnecting with family, spending quality time with friends, or working remotely in peaceful surroundings, this home offers everything you need for a memorable stay.

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!

Luxury Estate w/ Saltwater Pool, Hot Tub

Welcome to your secluded retreat—this elegant 5‑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), hot tub, 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