Vacation rentals with a pool in Calvert County

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Top-rated rentals with a pool in Calvert County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

A private salt-water pool is featured, surrounded by lush greenery. The pool's shimmering blue water reflects the sunlight, while a smooth entry step leads into the inviting space. A safety fence encloses the area, ensuring guest privacy.

Home in Lusby

4.92 out of 5 average rating, 79 reviews

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

Guest favorite

A spacious waterfront home is presented with a clear blue sky overhead. A well-maintained lawn surrounds a rectangular pool, with lounge chairs and umbrellas positioned nearby. The exterior features large windows and a covered porch, inviting relaxed outdoor living.

Home in Tilghman Island

4.97 out of 5 average rating, 30 reviews

Relax by the Water - Summer Dates Available!

STRN-24-62. Wonderful waterfront home. Minutes from St. Michaels offering all you'll need for the perfect vacation experience. Fabulous location with panoramic views of the water everywhere you look. Crab and fish from the dock. Hop on a bike and explore the island by land and then try out kayaks for a water adventure. Cool off with an afternoon dip in the pool. Enjoy starry nights at the waterfront firepit. If the bikes and kayaks wore you out relax your muscles in the hot tub. Perfect!

Top guest favorite

Farm stay in Huntingtown

5 out of 5 average rating, 55 reviews

Private Luxury Farmette -Huntingtown MD -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.

Guest favorite

An indoor pool area is surrounded by large glass windows, allowing natural light to illuminate the water. Tropical plants are positioned along the perimeter, enhancing the serene ambiance. A spa tub is integrated into the pool design, providing a relaxing focal point.

Home in Chesapeake Beach

4.92 out of 5 average rating, 119 reviews

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).

Top guest favorite

The backyard features a private pool surrounded by landscaped gardens and a variety of seating areas. Flowering plants add color to the foreground, while lounge chairs line the poolside. The house and trees are visible in the background, complementing the serene setting.

Home in Lusby

5 out of 5 average rating, 15 reviews

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.

The exterior view showcases a private pool surrounded by a spacious wooden deck. Lush greenery frames the home, which features a covered outdoor dining area and a bright umbrella to provide shade. The clean pool water reflects the surrounding trees and sky.

Cabin in Lusby

4.83 out of 5 average rating, 12 reviews

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.

Top guest favorite

A serene outdoor area features a saltwater swimming pool surrounded by comfortable seating, including wicker chairs and side tables. Lush greenery frames the space, with a view of the water beyond. Lanterns are placed around the pool for added ambiance.

Home in Tracys Landing

4.99 out of 5 average rating, 207 reviews

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!

Guest favorite

An aerial view of a spacious property featuring a private pool with a curvy shape. The home boasts multiple outdoor seating areas and is surrounded by a grassy yard. Solar panels are visible on the roof, and neighboring houses can be seen in the background.

Home in Tilghman

5 out of 5 average rating, 9 reviews

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.

Guest favorite

A softly illuminated in-ground swimming pool is surrounded by umbrellas and lounge chairs. The pool area is framed by trees, enhancing a serene atmosphere. A small pool house is visible in the background, with light glowing warmly from its windows.

Apartment in Mechanicsville

4.95 out of 5 average rating, 39 reviews

Living Water Farm

Calling all vacationers, singles, couples, families, friends, and professionals. This is a 100% smoke free property (no exceptions). Come enjoy this fully functioning in-law apartment in the basement of a 5K+ sq.ft. home on 9 acres of land. Spread out in 3 large bedrooms, living room, 2 full bathrooms, and full kitchen. Enjoy a 28k gallon in-ground swimming pool when open (Memorial Day through Labor Day)!

A clear swimming pool is surrounded by a wooden deck, featuring lounge chairs and a yellow inflatable float. The property includes a spacious house in the background, framed by lush greenery and trees, creating a relaxed outdoor atmosphere.

Home in Tilghman

5 out of 5 average rating, 3 reviews

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

Top guest favorite

Farm stay in Port Republic

5 out of 5 average rating, 104 reviews

Maple Hollow Farm - A Little Piece of Heaven

Enjoy the modern farmhouse charm of this lovely apartment here at Maple Hollow Farm! This space includes all new furnishings, appliances, amenities and unique, stylish decor. You will enjoy a spectacular view off the attached deck that typically includes the horses grazing in the pastures and an amazing sunset! It's a fabulous location for your next getaway or even stay-cation!