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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 spacesFamilyDecor

4.91 out of 5 average rating, 130 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.
Apartment 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 spacesLayout

4.85 out of 5 average rating, 116 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 spacesKitchenWalkability

4.9 out of 5 average rating, 112 reviews
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

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.

KitchenFamilyLaundry

4.98 out of 5 average rating, 257 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.

Indoor spacesFamilyParks

4.96 out of 5 average rating, 249 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.

FamilyKitchenAmenities

4.97 out of 5 average rating, 105 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.

KitchenFamilySleep quality

5.0 out of 5 average rating, 125 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.

KitchenFamilyBathroom

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!

KitchenFamilyAmenities

4.99 out of 5 average rating, 106 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.
Apartment 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.

KitchenFamilyTV

4.96 out of 5 average rating, 250 reviews
Top Guest favourite
Guest suite in Lusby

Waterfront on St. Leonard Creek at Fort Hill

Waterfront home on St. Leonard Creek w/ private pier for fishing and relaxing, PLUS a small beach area. Close to Solomons, fossil hunting at Calvert Cliffs, the Calvert Marine Museum (and their concerts), and other area attractions. Forget stairs! Our elevator directly connects the parking area to your private floor! Fort Hill is a uniquely quiet and private space with wide-open views of the outdoors. 4 kayaks are included FREE for you to enjoy!

Indoor spacesFamilyLocation

4.98 out of 5 average rating, 117 reviews
Guest favourite
The exterior of a spacious six-bedroom home is showcased, featuring a symmetrical façade with a blend of brick and siding. Large black-framed windows reflect a clear blue sky and white clouds, enhancing the inviting appearance of the property.
Home in St. Leonard

Large home w/ 6 Bedrooms, 7 Bathrooms, & Game Room

The Mackall House is a spacious fully-remodeled six bedroom home with two primary suites, five full baths, and two half baths! There are two full kitchens, a huge common area, and a large room downstairs with a pool table, foosball table and a shuffleboard table. There is deck off of the living room that overlooks the large backyard. This is the perfect place for up to 15 guests to comfortably stay! No parties or events are allowed at this time.

Indoor spacesFamilyWalkability

4.93 out of 5 average rating, 109 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
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.

FamilyKitchenGetting around

5.0 out of 5 average rating, 105 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

FamilyKitchenPets

5.0 out of 5 average rating, 186 reviews
Top Guest favourite
Cottage in North Beach

Waterfront Cottage Near Herrington and North Beach

Indoor spacesFamilyLayout

4.97 out of 5 average rating, 381 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

FamilyKitchenView

4.99 out of 5 average rating, 113 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 spacesKitchenDecor

4.96 out of 5 average rating, 76 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

FamilyKitchenGetting around

4.87 out of 5 average rating, 82 reviews
Top Guest favourite
Home in Lusby

Private Beach, Dock, Hottub @ Solomons Bay A-Frame

KitchenFamilyTV

5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in North Beach

Marina View Getaway | 3bd 2.5 bath

FamilyIndoor spacesBackyard

4.95 out of 5 average rating, 20 reviews

Family- and pet-friendly home rentals

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

FamilyIndoor spacesSleep quality

4.92 out of 5 average rating, 267 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

FamilyKitchenPool

4.92 out of 5 average rating, 106 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

Indoor spacesFamilyParks

4.83 out of 5 average rating, 223 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

FamilyIndoor spacesParks

4.89 out of 5 average rating, 321 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!

Indoor spacesFamilyLong stay

4.96 out of 5 average rating, 740 reviews
Top Guest favourite
A sunset view is revealed over the Chesapeake Bay, with warm colors reflecting on the water. Wooden deck furniture is positioned to enjoy the scenery, framed by tall trees along the shoreline. Gentle waves are visible in the foreground, enhancing the serene atmosphere.
Home in Lusby

Waterfront Home on the Chesapeake Bay-Pvt Beach

Indoor spacesKitchenBeach

4.95 out of 5 average rating, 186 reviews
Guest favourite
A bright living area is illuminated by large windows, providing a view of the surrounding greenery. A comfortable sectional sofa is arranged around a centerpiece coffee table, while a small pool table sits nearby. Natural light enhances the airy atmosphere of the room.
Home in Lusby

SoMD Waffle House 1.5 acres of cozy coastal living

KitchenFamilyNearby

4.91 out of 5 average rating, 119 reviews
Guest favourite
A serene waterfront view captures a glamping bungalow with a wooden pier, surrounded by lush trees. The calm water reflects the clear blue sky and the warm colors of the cabins. A boat is visible nearby, emphasizing the tranquil outdoor setting.
Houseboat in Hollywood

Charming Rustic Boathouse right on the Water!

KitchenFamilyParking

4.78 out of 5 average rating, 116 reviews

Family-friendly home rentals with a pool

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.
Guesthouse in St. Leonard

Studio on the Bay.

FamilyIndoor spacesBathroom

4.97 out of 5 average rating, 125 reviews
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

FamilyKitchenAccess

4.99 out of 5 average rating, 175 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

KitchenFamilyLaundry

4.99 out of 5 average rating, 251 reviews
Guest favourite
Home in Lusby

Spacious and private waterfront, sleeps 10

Indoor spacesKitchenAccess

4.92 out of 5 average rating, 93 reviews
Top Guest favourite
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.
Home in Lusby

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

Indoor spacesFamilyCheckout

5.0 out of 5 average rating, 45 reviews
Top Guest favourite
Guesthouse in Lusby

Quiet country retreat close to Solomons Island

Indoor spacesFamilyCheckout

4.97 out of 5 average rating, 35 reviews
Top Guest favourite
Home in North Beach

Stunning North Beach Getaway w/ Inground Pool

FamilyKitchenLocation

5.0 out of 5 average rating, 35 reviews
Guest favourite
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

Tranquility on Tilghman Island – Wide Water Views

KitchenIndoor spacesBeach

4.96 out of 5 average rating, 46 reviews

Destinations to explore