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

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, 147 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.

Guest favorite

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, 205 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, 178 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, 231 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

4.89 out of 5 average rating, 257 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, 324 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.

Superhost

Cottage in Saint Leonard

4.88 out of 5 average rating, 112 reviews

Spacious Beachfront Retreat w/Dock

Relax with the whole family at this peaceful place to stay. This charming home features 5 bedrooms and 3 full bathrooms. All bedrooms have a waterfront view. Enjoy watersports - kayaking, fishing, paddle boarding; or relax on the beach by a fire and enjoy the sunset. Bring your jet skis or fishing boat, the marina is 5 miles away.

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What guests are saying

Wits-end rustic beach cottage

5 out of 5 average rating, 4 reviews13 months ago

My family and I had a wonderful stay at Siobhan’s house. The house was bigger than expected with lots of room for our family of 5 plus two dogs. The doggie door was very convenient and the yard was a great additional hang out spot. Siobhan was very friendly and responsive. Highly recommended and will stay again!

Home in Chesapeake Beach

What guests are saying

Beachfront Oasis with Amazing Views

4.89 out of 5 average rating, 63 reviews3 days ago

Michael's place was perfect for our spring break getaway. I really liked the laid back beach vibe and how kid friendly the house was. The kids were able to walk to beach themselves and had a great time on the trampoline! We loved seeing who could find the most shark teeth.

Home in Lusby

What guests are saying

Charming Waterfront on Chesapeake Bay

4.89 out of 5 average rating, 364 reviews3 weeks ago

What a breathtaking experience to have after a stressful month! The community is so quiet and peaceful, the home is cluttered but executed in an inviting maximalist fashion that feels like a big hug of history. Between the morning views to the history written on the walls- the television wasn’t turned on once during our stay. We only had an issue with the key, but the host quickly responded and gave us instructions that solved it! Thank you for having us stay in your beautiful cottage.

Cottage in Tracys Landing

What guests are saying

Solomons Yellow House - Waterfront

4.96 out of 5 average rating, 26 reviews3 months ago

Really enjoyed holiday get away . Place was located near water with great views. We enjoyed walking around the neighborhood was quaint. The town was was pretty with water on each side with the Christmas lights at night . We truly enjoyed our relaxing stay . Would definitely book again

Home in Solomons

What guests are saying

Waterfront, Dog-friendly, Hot Tub, Peleton, Bikes

5 out of 5 average rating, 134 reviews1 month ago

This home and views are just gorgeous! Outstanding host with too many thoughtful extras to count! Charming town with good restaurants, a few cute shops, and great boardwalk by the beach. I hope we get an opportunity to visit again!! You won’t regret booking this place!

Home in North Beach

What guests are saying

Spacious and private waterfront, sleeps 10

4.92 out of 5 average rating, 79 reviews3 weeks ago

The location for this house is beautiful! We loved the private dock and spacious backyard. We stayed in late March so it was a bit cold some days but we still had a great time using the provided Kayaks and sitting on the dock and watching the beautiful surroundings. The location was perfect to have some s'mores nights around the firepit. The hosts were VERY responsive. The few times I had questions they replied within minutes and were very accomodating with our requests. They were very proactive with instructions and generously mentioned a foldable crib for the infant in our group - although we had our own that we used. The kitchen had all of the dinnerware and cookware that we needed for the meals that we made. The living areas were open and inviting. It was perfect for our group. One thing to watch for is the very steep driveway. It took a few times to get used to. We would definitely stay there again when we visit our family in the area.

Home in Lusby

What guests are saying

Hideaway on the Bay: Waterfront Vintage A Frame

4.93 out of 5 average rating, 194 reviews2 weeks ago

We spent a quiet and serene weekend at this place celebrating our 28th wedding anniversary. I liked the decor, the furniture were all extremely comfortable, and the view was amazing of course. The kitchen had all that we needed to cook a simple meal. I liked that oils and spices were provided in addition to coffee and tea. We enjoyed the outdoor space to have a campfire. (while sitting on the back deck looking out at the bay and night skies) We were also able to enjoy use of the tandem kayak and would recommend that to those who come as the creek was so smooth and fun to be on the water looking at nature and beautiful houses. Can definitely kayak to Vera's restaurant though return trip may take longer due to water current. We really enjoyed our long weekend and would recommend this location to others or come back ourselves.

Cabin in Lusby

What guests are saying

Bayfront Home with Amazing Rooftop Deck!

4.97 out of 5 average rating, 105 reviews4 months ago

I can’t adequately put into words how beautiful and stunning this home is. My family spent the Thanksgiving holiday here, and we loved every minute of our stay. There was more than enough space for all of us (about 15 total), and the views from this home are simply breathtaking. A bus stop that is about 1 block away made catching the bus into the city easy also. Though the home itself is amazing, superior customer service is what puts this home in a league of its own.Barbara answered my myriad of questions, checked in periodically with me, and ensured we had everything we needed. Curt even came on Thanksgiving to address a small issue we had with the elevator. I can’t recommend this place enough. If you are lucky enough to find this one available, do not hesitate in booking it.

Home in North Beach