Family-friendly vacation 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 favorite

Home in North Beach

4.98 out of 5 average rating, 60 reviews

The North Beach Retreat House

Completely remodeled home! Walk to local restaurants, charter fishing/crabbing, community pier & small beach. Fully furnished, hardwood floors, gorgeous kitchen with custom granite countertops, 3 full ceramic-tiled baths. 1st floor bedroom & full bath plus 2 bdrms & 2 baths upstairs. Plenty of parking, sleeps 8-10. Great location of a small town feel in a waterfront community, but so close to Washington DC (just 35 minutes)! Minutes from wedding venues of Rod 'n Reel & Herrington Harbor South.

Guest favorite

Home in Port Republic

4.88 out of 5 average rating, 24 reviews

Magical Bayfrnt Home, Pier, Beach, Fossils, trails

Free WiFi, kayak rentals. Our HOA precludes wedding or large gatherings. We are located on the Chesapeak's Bay Eastern shore, 14 miles north of Solomons Isld ,Calvert Cnty, Md Beautiful sunrises and panoramic bay views make this 3 bedroom, 2 full bath, vacation beach house (sleeps eight). Located in Southern Maryland’s Western shore, only 45 min from Washington, D.C, in a charming 15 home community. Fossils galore, walk 5 miles on the bay's sandy shores. 450 pier, kayaks available.

Superhost

Home in Saint Leonard

4.9 out of 5 average rating, 129 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

4.95 out of 5 average rating, 170 reviews

Waterfront Home on the Chesapeake Bay-Pvt Beach

A commanding view of the Chesapeake Bay. Enjoy walking the beach to Calvert Cliffs, bike to parks, art and cultural events. Enjoy the private beach with plenty of fine sand and gentle waves, great for teaching little one's water skills, playing with your canine companion or fishing/crabbing off the beach. You’ll love this waterfront hideaway because of the location, views, and the ambiance. My place is suburb for couples, solo adventurers, business travelers, families, and canine friends.

Superhost

Home in Saint Leonard

4.83 out of 5 average rating, 60 reviews

Cozy Beach House ~Fall Getaway

Beach Access in a quaint beach community. This vintage and cozy style house is well stocked with everything you need for a beach getaway. This cute, three bedroom house is great for relaxing and getting fresh air on our community private beach. Enjoy one mile of beach exploring the shoreline, cliffs and Bay water. Indulge eating at great restaurants, hiking beautiful trails, driving through scenic small waterfront towns, and so much more. Come see what Chesapeake Bay has to offer!

Guest favorite

Home in St. Leonard

4.91 out of 5 average rating, 173 reviews

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.

Home in Chesapeake Beach

4.78 out of 5 average rating, 54 reviews

The Beach House

Gorgeous, Bayside home with magnificent views of the Chesapeake Bay! Located just minutes away from Chesapeake Beach Resort and Spa Marina and Herrington on the Bay Resort and Marina, this big-bungalow can comfortably fit any wedding party, a family on a much needed vacation, or any city dweller looking for some quiet R&R. If you feel like leaving, which you probably won't, downtown Annapolis is just a 30 minute car ride and DC and Baltimore are 10 minutes more!

Guest favorite

Home in North Beach

4.97 out of 5 average rating, 104 reviews

Bayfront Home with Amazing Rooftop Deck!

Large, comfortable home is made for family and friends to get together (up to 15 guests). Your morning walk or jog is out the front door to the boardwalk or beach. Walk across the street for restaurants, ice cream, daily wine tastings, an organic market, yoga, spas, local art, antiques and a friendly hometown coffee shop. About an hour from DC, Baltimore & Northern Virginia, it is located 5 to 10 minutes from popular local wedding and event venues.

Guest favorite

Cottage in California

4.97 out of 5 average rating, 219 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

Rental unit in Solomons

4.99 out of 5 average rating, 272 reviews

Island Breeze Solomons

Cute studio apartment on charming Solomons Island. Walking distance to restaurants, live music, boat and kayak rentals. The kitchen has a full sized refrigerator, microwave, toaster, two burner hot plate and coffee maker. We provide all bedding and bath towels for two people. Enjoy your coffee ( provided) or wine on the deck in the fenced in side yard. One well-behaved pet is welcome. Please make sure you pay the pet fee.

Guest favorite

Home in Lusby

5 out of 5 average rating, 133 reviews

Historic Rousby Hall, Waterfront, Patuxent River

*Heated pool open to 11/11/24* 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-November 11th) with amazing river views.

Guest favorite

Cottage in Broomes Island

4.9 out of 5 average rating, 124 reviews

Gorgeous Waterfront Home!

Gorgeous waterfront property with all new furnishings and amenities! Feel free to bring your fishing rod, kayak or paddle board. Water access is just steps away. Bring your bicycle, it's a peaceful and scenic area with a marina & convenience store close by. Please note we DO NOT allow pets or more than 4 guest total. We also do not allow outside visitors or parties.