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Family-friendly vacation rentals in Calvert County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Calvert County

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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The vintage A-frame home is nestled amongst trees, featuring a deck with a canopy in the foreground. A stone path leads to the entrance, where large windows allow for ample natural light. The surrounding landscape is adorned with greenery and decorative plants.

4.93 out of 5 average rating, 210 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Top guest favorite

A peaceful sleeping area features a neatly made bed with floral-patterned bedding in blue tones. A wooden nightstand holds a book and a small plant, while a warm light illuminates the wall, creating a cozy ambiance.

5 out of 5 average rating, 378 reviews

Rest & Restore in our Treetop Loft w/ Beach Access

Come experience our tucked-away loft 5 minutes from beaches, 10 minutes to Solomons and Calvert Cliffs. Totally private above-garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, & kitchen. Enjoy quick Wi-Fi, a 40" Smart TV, a cozy queen bed, and comfy lounge chairs. Choose to stay in or adventure out. NOTE: Smoke-free & peanut-free property as we are allergic to both. Scent Free in your space. Air Purifier. Only safe Melaluca cleaning products.

Top guest favorite

The exterior of a single-story beach house is visible, featuring white siding and landscaped areas. A stone pathway leads to a cozy outdoor seating area with light cushions. Lush greenery and mature trees are present, contributing to a serene atmosphere.

4.99 out of 5 average rating, 218 reviews

Cove Point Cottage with Chesapeake Bay views

Welcome to our beach house, just a block from the Cove Point Beach on the Chesapeake Bay. Start your beach day by grabbing the beach wagon from the shed, loading it up with beach chairs, towels, and your cooler. A short stroll takes you to the beach, where you can spend the day searching for shark teeth and shells or swimming in the bay's refreshing waters. After a day in the sun, rinse off in our outdoor shower. Our shady patio provides the perfect spot to relax and enjoy the evening breeze.

Top guest favorite

Two light blue Adirondack chairs are positioned on a wooden dock, facing a calm river. The sun sets over the water, casting a warm glow across the surface and creating a serene atmosphere. A weathered wooden table is placed nearby, enhancing the inviting scene.

Guest suite in Lusby

4.98 out of 5 average rating, 353 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is Solomon’s island. This is a safe space for all🥰

A collection of various fossilized shark teeth is displayed on an orange background. The teeth are of different sizes and shapes, showcasing both small and large specimens, with some exhibiting intricate details. The vibrant color of the background contrasts with the dark tones of the teeth.

4.94 out of 5 average rating, 107 reviews

Soul Oasis - home on the Chesapeake Bay

You can hear the waves of the Chesapeake Bay from the new trex deck. The beach is a short walk away where you can find fossils and sharks teeth and see plenty of nature. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.

Top guest favorite

An open concept living area features a combination of seating, including two armchairs and a side table. A dining area with a striking blue rug and wooden chairs is visible in the background, alongside a well-lit kitchen area with modern appliances.

Guesthouse in Owings

4.95 out of 5 average rating, 107 reviews

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.

Top guest favorite

The exterior of a renovated beach house is depicted, featuring a wide entrance with steps leading to a spacious deck. The deck is furnished with a dining set and a shaded lounge area, while greenery surrounds the property, enhancing its tranquil setting.

5 out of 5 average rating, 192 reviews

Cove Point Beach Home 1 &1/2 blocks to Beach

"Welcome to our Beach House, located in the unique peaceful private beach community of Cove Point. You'll enjoy the tranquility and the beauty of living less than a 2 min walk to the sandy beach and just a few away from Solomon's Island, MD. Our home was just renovated and is ready for your family to enjoy, offering beach necessities (wagon, chairs, umbrella, & toys) and recreational equipment (bikes & kayaks). This will be your home away from home.

Top guest favorite

A spacious living area features a gray sofa adorned with cushions, positioned in front of a decorative coffee table. A vibrant wall art piece adds color to the room, while potted plants bring a touch of greenery. The open layout connects to the kitchen area, visible in the background.

Home in North Beach

4.97 out of 5 average rating, 157 reviews

Huge Beach Home | 2 King Bds | Backyard Dining

Welcome to Palm Haven at A Haven Away! Our home has 4 bedrooms (2 king beds + 2 queen beds). 2 mins to the beach, restaurants, and wetlands. We have a private, landscaped backyard perfect for dining and lounging. We provide beach passes, beach gear, games, a Pack & Play, and tips for jet ski rentals and day trips. The shed has a huge Smart TV. Fully-equipped kitchen. Single-story living with 2 bedrooms, accessible shower on the ground floor.

Top guest favorite

The historic home features a charming exterior with a mix of white clapboard and dark shingles. An inviting porch is framed by green shutters and surrounded by well-maintained landscaping. A gravel driveway leads to the front entrance, enhancing the property’s welcoming appeal.

5 out of 5 average rating, 145 reviews

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is located on the Patuxent River, outside of Solomons Island with a view of the river's opening to the Chesapeake Bay. The 16-acre property is adjacent to our very private conservation area that borders our 300-foot private beach. The year-round property has a pier, and in-ground pool (May-October) with amazing river views. Also hosts weddings+events up to 100 guests (additional event fee applies).

A wooden staircase illuminated by soft lights leads down to a private dock. Reflections of trees and evening sky are seen on the calm water of St. Leonard Creek. A sailboat is moored at the end of the dock, adding to the serene waterside ambiance.

4.9 out of 5 average rating, 274 reviews

Peaceful Waterfront Retreat on The Bay

Escape to a serene waterside cabin with a private dock on quiet St. Leonard Creek, just an hour from Washington, DC. This rustic studio offers a cozy retreat for solo travelers, couples, or small families looking for peace and relaxation. Whether you're here to unwind, work remotely, or explore the outdoors, you'll find plenty to enjoy—including two kayaks, two canoes, and stunning waterfront views.

Top guest favorite

A rustic red barn stands prominently against a sunset, framed by trees. White barn doors, featuring decorative stars, enhance the charm. The soft light of dusk casts a warm glow over the grassy landscape, creating a serene rural setting.

Farm stay in Port Republic

5 out of 5 average rating, 107 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!

A tranquil beach scene presents soft sand leading to calm water, framed by an open sky dotted with clouds. A weathered log rests on the shoreline, while distant rocky formations add interest to the horizon.

Cottage in Saint Leonard

4.95 out of 5 average rating, 151 reviews

Block to Private Beach, Screened deck, Hot Tub

Relax at this renovated cottage with views of the Chesapeake Bay! Features large screened deck, hot tub, around corner from private community beach where you can find fossils and shark teeth! (4 min drive to larger community beach.) (No cleaning fee and multi night discounts! Message us for monthly rates.)

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Calvert County family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Top guest favorite

An outdoor dining area is showcased on a spacious deck featuring a round table set with dishes and floral arrangements. Several wooden chairs surround the table, while a large umbrella provides shade. The scenic view of the Chesapeake Bay extends in the background.

Home in Huntingtown

4.99 out of 5 average rating, 89 reviews

Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck

A wooden dock extends into the calm water, framed by trees on either side. Soft orange and pink hues illuminate the sky during sunset, with the sun dipping below the horizon. Water reflects the colors of the sky, adding tranquility to the scene.

5 out of 5 average rating, 3 reviews

Waterfront home on Mill Creek-5BR-Hot tub & Kayaks

Top guest favorite

A serene dock extends over calm waters, surrounded by lush greenery. A small orange kayak is secured nearby. In the background, a custom waterfront home is nestled among tall trees, providing a natural and tranquil setting.

Home in Mechanicsville

5 out of 5 average rating, 81 reviews

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

A covered outdoor seating area is shown, featuring a rug and a wooden table surrounded by comfortable chairs. Green trees provide shade, and a view of the calm waterfront and distant shoreline can be seen, creating a serene outdoor space for relaxation.

Cottage in Lusby

5 out of 5 average rating, 6 reviews

Riverside Haven w/ Hot Tub

Top guest favorite

A spacious outdoor deck is furnished with a sectional sofa arranged around a central table. Soft lighting from string lights enhances the atmosphere. In the corner, a hot tub is positioned, surrounded by nature and trees that create a serene backdrop.

Cottage in Lusby

5 out of 5 average rating, 19 reviews

Cozy Cottage close to Beaches & Solomon’s Island

Top guest favorite

A comfortable living area is framed by large windows showcasing a vibrant sunset over the water. Soft furnishings include two chairs with decorative pillows and a coffee table. Plants are positioned thoughtfully, enhancing the serene atmosphere.

Home in North Beach

5 out of 5 average rating, 147 reviews

Waterfront, Dog-friendly, Hot Tub, Peleton

A spacious living area is featured, showcasing a floral-patterned sofa and a glass coffee table. Decorative elements such as potted plants and an ornate display cabinet with collectibles create a homey environment. Natural light fills the space from large windows, enhancing the warm tones of the decor.

4.85 out of 5 average rating, 46 reviews

Waterfront home with three bedrooms,3 full baths

Top guest favorite

An entryway leads through tall grasses and dunes to a sandy beach covered with colorful umbrellas. The clear blue sky and calm water create a serene setting, while beachgoers enjoy the day in the distance.

Guesthouse in Saint Leonard

4.96 out of 5 average rating, 113 reviews

Studio on the Bay.

Family- and pet-friendly home rentals

A spacious wooden deck offers a view of the calm waters of the Chesapeake Bay. Picnic tables are arranged for outdoor gatherings, with marshland visible in the background. Houses line the opposite shore, under a partly cloudy sky.

Home in North Beach

4.82 out of 5 average rating, 207 reviews

Warm Home Overlooking the Chesapeake Bay

A charming two-story home is set against a clear blue sky, featuring a white exterior and a welcoming front pathway made of stone. Lush green grass surrounds the house, complemented by a white picket fence and well-maintained landscaping.

Home in Solomons

4.93 out of 5 average rating, 111 reviews

Roomy 6 bedroom home in the heart of Solomons, MD

A spacious living area features large glass windows that frame a panoramic view of the Chesapeake Bay. Natural light illuminates the room, highlighting the wooden ceiling and modern decor. A seating arrangement overlooks an inviting outdoor patio with garden furniture, creating a seamless connection to the outdoors.

4.96 out of 5 average rating, 149 reviews

Coastal Oasis On The Chesapeake, King Bd sleeps 12

Top guest favorite

A light and airy living area features a comfortable brown sofa adorned with decorative pillows. A television is mounted on the wall, alongside coastal-themed artwork. A dining table with four chairs and a small deck can be seen in the background, enhancing the open layout.

Townhouse in North Beach

4.98 out of 5 average rating, 46 reviews

Beach Passes! Family & Dog Friendly w/ Fenced Yard

Top guest favorite

Guesthouse in Mechanicsville

4.99 out of 5 average rating, 91 reviews

Barnyard Retreat

The exterior of a two-story beach house is shown, featuring white siding and dark shutters. A welcoming front porch is visible, adorned with a small American flag. A pathway leads through green grass to the entrance, surrounded by landscaped shrubs.

Apartment in North Beach

4.89 out of 5 average rating, 88 reviews

Spacious Beach House Top Floors - Walk Everywhere!

Top guest favorite

A dining area is presented with a modern table surrounded by white chairs, offering a casual atmosphere. Natural light pours in through large windows. A beach-themed artwork depicting a tropical scene enhances the setting, while a coffee bar is conveniently located nearby.

Cottage in North Beach

4.96 out of 5 average rating, 164 reviews

Bell Estates I Beautiful Cottage I *Beach Passes*

A stone pathway leads to a two-story house with white siding and turquoise accents. A fenced yard features a well-maintained lawn. The entrance is adorned with a porch that includes two chairs, providing a welcoming space for relaxation. Overhead, the sky presents a mix of clouds.

Home in Solomons

4.89 out of 5 average rating, 144 reviews

Perfect spot for a Vacay!

Family-friendly home rentals with a pool

Top guest favorite

The two-story farmhouse features a white exterior with black accents and a welcoming porch. Rocking chairs are positioned under the covered area, surrounded by neatly manicured gardens and lush greenery. Overcast skies lend a tranquil mood to the comfortable outdoor space.

Farm stay in Huntingtown

5 out of 5 average rating, 68 reviews

Luxury Farmette -Private-Saltwater Pool -1hr to DC

A serene waterfront scene shows a calm river with two boats docked at a wooden pier. Nearby, a sandy beach is bordered by green grass, while a gentle slope leads to the water. A distant American flag flutters in the breeze against a clear blue sky.

Farm stay in Mechanicsville

5 out of 5 average rating, 3 reviews

Trent Hall Retreat

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.

4.91 out of 5 average rating, 82 reviews

Spacious and private waterfront, sleeps 10

Top guest favorite

A tranquil view of the private pool framed by potted plants featuring colorful flowers. The pool area extends towards a serene body of water, surrounded by trees. The distant shore is visible, enhancing the natural beauty of the setting.

5 out of 5 average rating, 25 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

An outdoor oasis showcases a sparkling pool with a built-in spa, surrounded by lush greenery. Comfortable lounge chairs are positioned on the patio, providing a serene space for relaxation. The textured stone patio complements the natural setting, offering a tranquil retreat in a private environment.

Home in Port Republic

4.77 out of 5 average rating, 31 reviews

Family-Friendly Country Home • Pool, Spa + Games

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

4.94 out of 5 average rating, 36 reviews

Relax by the Water - Summer Dates Available!

A view of the modern house showcases its two-story design with a green metal roof. Surrounding the inviting in-ground pool are landscaped gardens and pots with small plants. The outdoor area provides a serene setting, complemented by vibrant greenery in the background.

Home in Saint Leonard

5 out of 5 average rating, 3 reviews

Spacious Private Retreat on the Patuxent River

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

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