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Family-friendly holiday rentals in Calvert County

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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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Guest favourite
A charming cottage exterior showcases a well-maintained garden with colorful flowers lining the pathway. The front porch features a welcoming entrance, while large windows provide ample natural light. A white picket fence frames the lush greenery that surrounds the home.
Cottage in North Beach

Quiet Coastal Cottage Escape with Water Views

Want to get away? Come relax and escape in our updated bay view cottage. You'll enjoy stunning sunsets, warm surroundings, and all the amenities you could want in our cozy, peaceful cottage home. You'll find plenty of comfortable spots to relax, inside and out. Located on a quiet street, while still close to the small-town charm and offerings of North Beach, Chesapeake Beach, and Herrington Harbor. Walk along the bay, enjoy the local restaurants, and get ready to relax. Stay a week and save!

Indoor spacesFamilyHospitality

4.91 out of 5 average rating, 133 reviews
Top guest favourite
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

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

Custom waterfront home with everything you need to relax and recharge. Two levels of decks offer amazing views of the changing tides on Cat Creek. Soak in the hot tub and watch the eagles soar by, or head down to the dock for crabbing, fishing, and kayaking during high tide. Located in historic Southern Maryland, this quiet, hidden estuary makes for a unique getaway with great amenities. Fast WiFi for work, game room for fun, and a fenced-in yard for dogs. 1 hour from DC but feels worlds away.

KitchenIndoor spacesAccess

5.0 out of 5 average rating, 107 reviews
Superhost
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.
Flat in North Beach

Spacious Beach House Top Floors - Walk Everywhere!

This booking is for the entire SECOND story & loft of a DUPLEX-style beach house. Entrance, access, & all indoor spaces of the unit are private, however there are often other guests and families on the first floor. There is also a STAIRCASE to the 2nd floor unit and a STAIRCASE to the loft. Please ensure this home suits your needs. The space has an open floor design with 14' cathedral ceilings for a spacious modern feel with beach-house charm. Walk 2 blocks to the beach, boardwalk, and more!

KitchenIndoor spacesSleep quality

4.85 out of 5 average rating, 117 reviews
Top guest favourite
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.
Home in Lusby

Soul Oasis - home on the Chesapeake Bay

Listen to the waves of the Chesapeake Bay from the trex deck. There are 2 private community beaches in the neighborhood where you can find fossils and sharks teeth. 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 around the house! 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.

KitchenFamilyNearby

4.95 out of 5 average rating, 146 reviews
Top guest favourite
The front porch of the cottage features two white rocking chairs positioned on a gray deck. A small table sits between them, and a potted flower adds a touch of color. An American flag is displayed, and large windows provide views of the surroundings.
Home in North Beach

Charming Historic 2 Bedrooms on the Chesapeake Bay

Come visit North Beach, Maryland! Enjoy year-round activities, crab houses, and great restaurants. Our quaint 100-year-old cottage sits directly on the Chesapeake Bay. Relax on the front porch and watch the sunrise. Take a short walk to the charming shops and eateries. The comfortable cottage has everything you need for a getaway. Just a stone’s throw away from the half-mile-long boardwalk and bike trails. Stroll to the Saturday morning Farmer’s Market, First Fridays, and movies on the beach!

Indoor spacesKitchenBathroom

4.9 out of 5 average rating, 114 reviews
Top guest favourite
A comfortable living area features a plush blue sofa with pink accent pillows, complemented by a round mirror. Decorative plants add a touch of greenery. A light wooden coffee table supports a floral arrangement, while two poufs create additional seating in a welcoming space.
Townhouse in North Beach

Beachside Oasis + Beach Passes | A Haven Away

Welcome to Bay Haven, one of five A Haven Away getaways! This plant-filled oasis is in a quiet North Beach neighborhood, steps from the wetlands park and 12 minutes on foot to the beach. We share our community beach passes and loads of local tips. The house is stocked with everything you need for a relaxed stay. 12 min walk to the beach, boardwalk, restaurants, and kids play areas in North Beach, MD 7 min drive to Herrington Harbor 14 min drive to Tacaro Estate Find us on Insta ahavenaway.

KitchenFamilyOutdoor spaces

4.96 out of 5 average rating, 252 reviews
Top guest favourite
The exterior of a two-story house is showcased, featuring light blue siding and white railings. A grassy area is visible in front, with four gray Adirondack chairs arranged around a circular fire pit on a stone patio. The sun casts a warm glow over the scene.
Home in Solomons

The Little House on Back Creek

Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

FamilyIndoor spacesHot tub

5.0 out of 5 average rating, 143 reviews
Top guest favourite
A bright and open living space features large windows that provide views of the river. A long dining table is accompanied by upholstered chairs. A modern kitchen counter with stools is visible, along with a chandelier overhead and a cozy fireplace on one side.
Home in St. Leonard

Blue Pearl-Luxury estate with private dock/jacuzzi

The Blue Pearl is a luxurious river front estate with a private pier to catch crabs, fish and kayak. Soak in the outdoor jacuzzi and enjoy the river life. Three bedrooms with three full bath en-suites and over 2800 square feet of luxury accommodations await you. Office has Queen sleeper sofa. Pull up to your private boat dock, catch blue crabs with the provided traps, toast s’mores in the firepit while sitting in your Adirondack chairs. Enjoy two decks to view the sunrises and sunsets.

FamilyIndoor spacesWifi

4.97 out of 5 average rating, 107 reviews
Top guest favourite
Farm stay in Huntingtown

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.

KitchenIndoor spacesHospitality

4.99 out of 5 average rating, 129 reviews
Top guest favourite
The exterior of the house showcases multiple large windows that invite natural light, with a spacious porch area featuring white outdoor chairs. Colorful flower planters enhance the surroundings, providing a serene setting among greenery.
Home in St. Leonard

Cozy Cottage on the Chesapeake Bay

Tranquility supreme. Sit on the terrace and gaze at the Chesapeake Bay. Sandy beach -- just 50 steps from front door; quiet residential area; nearby antiquing & fishing; Only 75 min. from DC. Finish your book or just replenish your spirit. Enjoy. Oh, one more thing — looking for the perfect place for a retreat for your small DC team? Strategic planning will be even more creative and enjoyable when you have the Chesapeake Bay as your muse. Note: This property is for non-smokers.

Indoor spacesFamilyLong stay

4.92 out of 5 average rating, 199 reviews
Top guest favourite
An exterior view of the home showcases a light grey facade with a gentle slope roof surrounded by trees. A gravel driveway leads to the entrance, while a calm waterway with a boat dock is visible in the background.
Home in Hollywood

Waterfront Home: Osprey Getaway

Welcome to The Osprey Getaway! This spacious home is the perfect destination for families seeking a relaxing retreat. Our home is not far from Solomon’s Island, Patuxent River Naval Air Station, St. Mary’s College of Maryland, and historic Leonardtown. Here you'll find an open floor plan and plenty of space to unwind and take in your surroundings. Enjoy the peace and quiet of Cuckold Creek and the beauty of our newly renovated home. We can't wait to share our home with you!

KitchenFamilyCheck-in

4.99 out of 5 average rating, 109 reviews
Top guest favourite
A red umbrella provides shade over a square table with a glass top, accompanied by two cushioned chairs. Lush green grass surrounds the seating area, framed by tall trees and distant views of the water, creating a serene outdoor space.
Flat in Port Republic

Serenity Suite on Chesapeake Bay

Come enjoy our waterfront home on the scenic Calvert Cliffs. Take in beautiful Bay views in Adirondack chairs with stunning vistas. Photograph wildlife. Comfortable ½ mile walk to private community bay shoreline. Have breakfast in the yard while enjoying the sunrise. Stroll the community shoreline and explore fossil hunting, hike at nearby trails. No pets are allowed because I have a severe allergic reaction to pet hair and dander. Thanks for your understanding.

KitchenFamilyQuiet

4.96 out of 5 average rating, 253 reviews

Popular amenities for Calvert County family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favourite
Cottage in North Beach

Waterfront Cottage Near Herrington and North Beach

Indoor spacesFamilyGetting around

4.97 out of 5 average rating, 381 reviews
Top guest favourite
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

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

Indoor spacesKitchenBeach

5.0 out of 5 average rating, 189 reviews
Guest favourite
An aerial view showcases a lush green landscape surrounding a peaceful shoreline. The sandy beach meets calm waters, framed by dense trees. The varied colors of the water create a serene contrast against the vibrant greenery, presenting a tranquil natural setting.
Cottage in Lusby

Hot Tub Hideaway by Shark Tooth Shores

KitchenIndoor spacesAccess

4.85 out of 5 average rating, 101 reviews
Top guest favourite
A sandy beachfront scene features a log cabin surrounded by lush greenery. A well-maintained lawn leads to a gently sloping beach, where the calm waters meet the shore. Multiple seating areas, including lounge chairs, are visible along the edge of the water.
Cabin in Lusby

Bayfront Walk-Out Beach Home | Sunrise & Fire Pit

FamilyKitchenValue

4.99 out of 5 average rating, 114 reviews
Guest favourite
An aerial view captures a spacious home with a modern Cape Cod style, featuring multiple outdoor decks furnished with umbrellas and seating. A well-maintained garden surrounds the property, enhancing the natural beauty and providing a secluded, inviting area for relaxation.
Home in Mechanicsville

Private, Lakefront Oasis- Lavinia by the Lake

Indoor spacesKitchenNearby

4.96 out of 5 average rating, 79 reviews
Guest favourite
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.
Home in Lusby

Waterfront home with three bedrooms,3 full baths

Indoor spacesFamilyGrill

4.87 out of 5 average rating, 85 reviews
Top guest favourite
Home in Lusby

Sandy Beachfront A-Frame w/ Hottub & Private Dock

FamilyIndoor spacesHot tub

5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in North Beach

Marina View Getaway | 3bd 2.5 bath

KitchenFamilyHot tub

4.96 out of 5 average rating, 24 reviews

Family- and pet-friendly home rentals

Top guest favourite
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.
Home in Lusby

Cove Point Cottage with Chesapeake Bay views

KitchenIndoor spacesCheck-in

4.98 out of 5 average rating, 261 reviews
Guest favourite
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.
Cabin in Lusby

Hideaway on the Bay: Waterfront Vintage A Frame

Indoor spacesFamilyView

4.91 out of 5 average rating, 269 reviews
Top guest favourite
Guest suite in Lusby

Waterfront on St. Leonard Creek at Fort Hill

Indoor spacesKitchenCondition

4.98 out of 5 average rating, 119 reviews
Guest favourite
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.
Cabin in Lusby

Peaceful Waterfront Retreat on The Bay

KitchenIndoor spacesCondition

4.89 out of 5 average rating, 323 reviews
Top guest favourite
A charming white cottage presents a welcoming facade, featuring a covered porch with two light blue chairs and a small table. A well-maintained lawn with green grass and a landscaped border is visible, while a white picket fence enhances the front yard.
Cottage in North Beach

Club Carp North Beach - Steps to the Bay!

KitchenFamilyHospitality

4.95 out of 5 average rating, 181 reviews
Superhost
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

Warm Home Overlooking the Chesapeake Bay

FamilyKitchenPets

4.83 out of 5 average rating, 226 reviews
Top guest favourite
A serene sunset casts vibrant hues of pink and orange across the water. The pier is seen in the distance, with the silhouette of a bridge spanning the horizon. Two figures are visible swimming, creating gentle ripples in the calm water.
Tiny home in Solomons

“Cabana by the Bay”-tiny home on a pier!

KitchenFamilyGetting around

4.96 out of 5 average rating, 745 reviews
Guest favourite
The lake house is surrounded by vibrant autumn foliage, showcasing a two-story structure with a spacious deck. Large windows allow natural light to brighten the interior. The inviting outdoor space features a neatly landscaped yard, providing a serene view of the surrounding woods.
Home in Lusby

Spacious Lake House at the Chesapeake Bay

FamilyKitchenBack garden

4.92 out of 5 average rating, 107 reviews

Family-friendly home rentals with a pool

Top guest favourite
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.
Home in Lusby

Historic Rousby Hall, Waterfront, Pool, Beach

FamilyKitchenAir conditioning

4.99 out of 5 average rating, 179 reviews
Top guest favourite
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.
Guest house in St. Leonard

Studio on the Bay.

KitchenFamilyAccuracy

4.97 out of 5 average rating, 126 reviews
Top guest favourite
A spacious living area features two comfortable sofas, one draped with a soft blanket. Natural light streams through large windows, highlighting the wooden flooring. A small wooden table is visible in the background, and a decorative piece hangs above the mantel.
Home in Tracys Landing

The Little Gypsy BoHome

FamilyKitchenQuiet

4.99 out of 5 average rating, 255 reviews
Superhost
Home in Port Republic

Cozy 5-Bed Retreat, Heated Spa

Indoor spacesKitchenBathroom

4.78 out of 5 average rating, 60 reviews
Top guest favourite
The exterior of the home is showcased, featuring a classic white facade with two columns supporting the upper porch. A landscaped yard with colorful foliage and stones frames the outdoor seating area, which includes chairs and decorations. Natural light highlights the inviting entrance.
Home in California

Waterfront, pier, hot tub, pool, pizza oven

FamilyKitchenCheck-in

4.98 out of 5 average rating, 43 reviews
Guest favourite
Home in Lusby

Spacious and private waterfront, sleeps 10

Indoor spacesFamilyHospitality

4.92 out of 5 average rating, 93 reviews
Top guest favourite
Guest house in Lusby

Quiet country retreat close to Solomons Island

Indoor spacesFamilyQuiet

4.95 out of 5 average rating, 39 reviews
Top guest favourite
Home in North Beach

Stunning North Beach Getaway w/ Inground Pool

FamilyIndoor spacesBathroom

5.0 out of 5 average rating, 37 reviews

Destinations to explore