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

A bright living area features stylish seating arrangements with two blue sofas and a central ottoman. A wall-mounted television is positioned beneath decorative shelving. An open kitchen space is visible, showcasing modern bar stools and a dining area bathed in natural light from a nearby window.

Condo in Annapolis

4.94 out of 5 average rating, 389 reviews

Brand New Reno in Historic Dist w 2 Parking spots

Spotless / sanitized !! Renovated upstairs unit two bedroom with TWO parking spots in the Historic District. Everything is high end, brand new and used exclusively as a short term rental. Private entrance, cute small custom kitchen, ceiling fans, mini split AC/ heat in every room for year round comfort. Hardwood floors, quality linens, lucid mattresses, Keurig coffee bar, toiletries. Walk to town in 10 min or less or take the free trolley to Main St, USNA, Churches, AYC. No children under 10.

Guest favorite

A serene waterfront scene is captured just before twilight, showcasing calm waters reflecting the soft colors of the sky. Distant lights from nearby docks create a gentle glow, framed by the silhouettes of trees and the peaceful harbor setting.

Apartment in Annapolis

4.92 out of 5 average rating, 101 reviews

Dazzling day/night water views,1st class amemities

TREAT YOURSELF! YOU DESERVE THE VERY BEST! HUGE DISCOUNTS FOR WEEK AND MONTH LONG STAYS! Treat yourself to the good life while in Annapolis! Gorgeous 14yr. old custom designed & furnished 1470sq.ft. waterfront apartment, 9ft. ceilings, fantastic water views day & night! Private pier, firepit and 40ft. waterfront covered patio for guests use. Guest parking for 4 cars. Few minutes to US Naval Academy, Annapolis Harbor, restaurants, shopping. Pet-friendly, must be cleared with host. *see below*

Superhost

A well-lit bathroom features a spacious vanity with dual sinks, complemented by a large mirror above. A glass shower enclosure is present, along with a toilet positioned nearby. The floor showcases a unique blue patterned design, enhancing the overall clean and modern look of the space.

Home in Queenstown

4.81 out of 5 average rating, 156 reviews

Bay Breeze Retreat

Incredible private luxury retreat on the eastern Chesapeake Bay. Complete with every amenity- saltwater pool, firepit, multiple Smart TVs, sleeps 10 in comfort, premium memory foam mattresses in every room, fast Wi-Fi, 100' pier, huge front yard. Unbelievable views!!! Extensively renovated. Please note that no parties or disturbances will be tolerated. We require that guests respect our neighbors and serene community at all times. We explicitly do not allow bachelor or bachelorette parties.

Guest favorite

A serene waterfront view showcases the Chesapeake Bay, stretching towards the horizon under a clear sky. The shoreline features wooden docks and gentle waves, while quaint homes are seen along the sandy beach. Green trees provide shade in the foreground.

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

Top guest favorite

A colorful playground is situated under a canopy of trees, featuring a variety of play structures including slides, climbing frames, and swings. The ground is covered in wood chips, creating a safe play environment, while open grassy areas invite outdoor activities.

Place to stay in Annapolis

4.94 out of 5 average rating, 120 reviews

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

*Hot tub* “Chesapeake Bay View Paradise" (3BR/2BA Penthouse Suite). Private penthouse level of a 2-level duplex, new deck, gorgeous Chesapeake Bay views, steps to sandy beach. 3 car parking. Gourmet kitchen, SS appl, granite counters, bar. Comfy living & dining areas. Entry handrail installed 9/20/24. 2 King BR, 1 Queen BR + Queen sleeper sofa in living area. Sleeps 8. 2 spa inspired baths, 1 jetted 2-person Jacuzzi tub inside. Outdoor Spa with Jets * Best Places To Stay Annapolis

Guest favorite

A spacious grassy yard is highlighted by a colorful playset, equipped with slides and climbing features. Sunlight filters through surrounding trees, casting gentle shadows on the lawn. The area is open and well-maintained, suitable for outdoor activities and play.

Apartment in Arnold

4.96 out of 5 average rating, 174 reviews

Celebrate Summer by Your Private Pool

Lovely 2 acre waterfront lower level attached apartment with separate private entrance. Exceptional amenities include an inground pool, a pier with kayaks and paddle boards, pickleball and basketball courts, a swing set with a rock wall for kids, a gas grill, and a pool table. This amazing water front home is conveniently located only seven miles from the Naval Academy and downtown Annapolis. We do not host parties or events. Only registered guests are permitted on the property.

Superhost

A spacious living area showcases a comfortable gray sofa with accent pillows. A wooden dining table is surrounded by upholstered chairs. Large windows allow natural light to flood the room, highlighting framed artwork on the walls and a warm wooden floor.

Home in Annapolis

4.85 out of 5 average rating, 221 reviews

Spacious Home in Private Neighborhood with Beach

A beautiful and spacious home located on the Severn River in the gated community of Epping Forest! The house is just 7 miles from downtown Annapolis and offers guests a private, secluded home away from home. A private beach and club house are located within walking distance! Enjoy a fire on either of the two levels of private decks, or gather around the large dining room table for any of the provided board games. An abundance of amenities will make your stay more than comfortable!

Guest favorite

A modern studio loft features an open layout with a cozy leather couch, coffee table, and well-appointed kitchenette. Skylights and large windows offer natural light, while a decorative rug adds warmth to the space. A stylish ceiling fan enhances air circulation.

Apartment in Deale

4.91 out of 5 average rating, 620 reviews

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise

Gift yourself this private, secluded second floor Flat & Solarium Bedroom. Best hideaway to rest, bond, restore, create, or work. A breezy, country-like setting provides space to escape the city hustle! Nearby scenic drives & groceries, or venture to Annapolis TJ/WF or historic walks. Fully relax with pier, kayaks, swings, fire pit, starry nights, sun-drenched loungers, cozy up with books/movies & luxuriate in the deep soaking tub or European shower.

Guest favorite

The exterior of the cottage features a welcoming yellow facade, complemented by a manicured lawn with shrubs and mulch. A wooden deck with white columns provides entry to the front door, which is flanked by large windows. An American flag hangs proudly to the left.

Cottage in Colonial Beach

4.93 out of 5 average rating, 169 reviews

Bayside Cottage- In the Town with views

Welcome to Bayside Cottage, a newly renovated beach cottage in the very charming (Town of Colonial Beach), Virginia! The cottage boasts 3 bedrooms and 2 full baths and is centrally located in town. Walk across the property to Bayside Marina, where you can watch the sun go down on the rooftop deck with a drink in hand (contact host for instructions) Bayside Cottage was recently fully renovated and is best suited for groups of 6.

Superhost

A well-lit workspace features a white desk and a modern chair, surrounded by a tall white bookshelf filled with assorted books. Natural light enters through a window with blinds, while wood flooring adds warmth to the room.

Townhouse in Washington

4.85 out of 5 average rating, 377 reviews

MODERN HOME NEAR CAPITOL HILL ✩✩✩✩✩ Walk to METRO subway

♢ 2 blocks to the nearest Metro subway station ♢ 8-minutes by car to downtown Washington DC ♢ HDTV + Roku TV in living room & Master bedroom ♢ Amazon's Alexa at your service on the Echo ♢ High-speed Wi-Fi ♢ Kid- and family-friendly rental Relax in style in this lovely DC home, located just minutes from Capitol Hill and the must-see H St. Corridor in the Hill East community, and just a short metro ride from the museums.

Top guest favorite

A decorative welcome sign hangs on the door, featuring a serene beach scene with two adirondack chairs. The sign is framed by an oval glass design, enhancing a cheerful first impression for guests entering the home.

Home in Lusby

4.99 out of 5 average rating, 295 reviews

Cove Point Beach Cabin

My place is close to shopping, restaurants and dining in Lusby and Solomons Island, the Chesapeake Bay, and family-friendly activities. You’ll love my place because of the comfy beds, the coziness, and the views. My place is good for couples, solo adventurers, business travelers, and families (with kids). No pets allowed.

Top guest favorite

A bright common room features a comfortable white sofa paired with a glass coffee table. A small wooden table with a floral arrangement is positioned nearby. A map adorns the wall, and a kitchenette area includes a toaster and coffee setup, providing convenience for guests.

Guest suite in Annapolis

4.95 out of 5 average rating, 192 reviews

Cozy Naptown Perch

Perfectly Placed Perch in Murray Hill neighborhood. 1 mile to USNA stadium; 1 mile to historic downtown. Walk to local restaurants, in town events. Few blocks to water access. 2 bedroom upstairs suite recently renovated. Common room has sofa, table and chairs, coffee/ tea set up. Patio, fire pit available to guests.