Kid-friendly vacation rentals in Calvert County

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Calvert County

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

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Guest favorite

Cabin in Lusby

4.93 out of 5 average rating, 191 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 --

Guest favorite

Apartment in North Beach

4.97 out of 5 average rating, 127 reviews

Bayside Oasis of Southern Maryland

1 1/2 blocks from the beautiful Chesapeake Bay. Walk to boardwalk, restaurants and shopping. Beach opens, with some restrictions, May 28, 2021. Free beach pass provided. Quiet friendly town where everyone knows your name. King bed, private bath with shower (no tub). Free WiFi, private off street parking, 45” TCL-Roku TV, Echo Dot, Keurig w/pods for coffee and tea, full kitchen (no dishwasher), beach chairs, beach towels, dishes, flatware, pots pans. Chesapeake Beach is 1-mile south on Rt 262.

Top guest favorite

Cottage in North Beach

4.98 out of 5 average rating, 145 reviews

Bell Estates-Brand New Bay View, Beautiful Cottage

Bell Estates is a newly built corner lot across the street from the bay with minimal views of the water from Master bedroom and front yard. Located in the heart of North Beach in the exclusive Holland Point neighborhood, our home provides a cozy get-a-way for a family looking to escape the hustle and bustle of life. Home is 2 minutes away from Herrington Harbor, Ketch 22, North Beach Boardwalk & more. Enjoy local accessibility to fishing from the boardwalk dock or rent a boat to go crabbing.

Guest favorite

Cottage in North Beach

4.94 out of 5 average rating, 159 reviews

Club Carp North Beach - Steps to the Bay!

Calendar open for bookings in April 2025! Welcome to Club Carp North Beach. A charming and cozy cottage just 3 blocks to the Boardwalk/Beach. Renovated throughout with 3 bedrooms and 2 full baths. Perfect place for a relaxing, family vacation! This kid-friendly home has a large fenced side yard with swing set, play area for the kiddos, and lots of extra amenities with families in mind. Comfortable outdoor dining area with fire pit and gas grill. Just steps to restaurants, shopping, and bars.

Superhost

Home in Saint Leonard

4.9 out of 5 average rating, 130 reviews

Perfect Bay and Beach Getaway one hour from DC!

Our waterfront home with sweeping views of the Chesapeake Bay is close to beaches, the Flag Harbor Marina, Solomon's Island, Flag Pond Nature Preserve and Calvert Cliffs State Park. You’ll love the spectacular sunrises/sunsets over the Bay, diving ospreys and eagles, and exploring the bay by kayak, canoe, or paddle board. Our house is great for families (with kids), groups, and well-mannered dogs. New in 2023: we will be replaced the upstairs HVAC system, baby proofing, and fall 2023 paint

Guest favorite

Home in Lusby

4.87 out of 5 average rating, 138 reviews

The Calvert Cliffs Cottage

Welcome to the Calvert Cliffs Cottage. Nestled in a quiet country setting our home offers quick access to state parks and beaches, desirable Solomons Island, and a retreat from the world. Guests can expect a welcoming stay with all your essentials for a long or short term visit plus extra touches to make your experience memorable. Enjoy the fire pit with stunning historic barn as a backdrop or walk to the famous Calvert Cliffs State Park with family for a day of fossil exploration.

Guest favorite

Townhouse in North Beach

4.96 out of 5 average rating, 196 reviews

Beach Home | King Bed | Beach Passes | Cute Town

Welcome to Bay Haven at A Haven Away! Relax in a plant-filled oasis which offers the perfect setting to unplug, relax, and connect with loved ones. Its prime location is in walking distance to ice cream shops, lots of fresh seafood, and wetlands. We can't wait to share our local recommendations so you can enjoy our little slice of heaven. 12 min walk to the beach, boardwalk, restaurants, and kids play areas in cute North Beach, MD 7 min drive to Herrington Harbor

Top guest favorite

Home in Tracys Landing

4.99 out of 5 average rating, 203 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!

Top guest favorite

Home in Lusby

5 out of 5 average rating, 175 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

Cottage in California

4.97 out of 5 average rating, 230 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has an open floor plan that allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum featuring live concerts by top name bands.

Guest favorite

Cabin in Lusby

4.91 out of 5 average rating, 254 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

Cottage in North Beach

4.97 out of 5 average rating, 320 reviews

Waterfront Cottage Near Herrington and North Beach

Escape to Osprey Cottage, a renovated oasis overlooking the Chesapeake Bay. Our home is a 1930s bungalow that has been tastefully updated with modern sensibility, while still preserving its original charm. Streamlined decor, gleaming wood floors, and stunning views from the common spaces, deck, and hot tub invite you to simply relax.