
Family-friendly holiday rentals in Southern Maryland
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Southern Maryland
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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 --
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Waterfront with sweeping bay view & private beach
Year-round private beach oasis on Chesapeake Bay! Perfect Fall & Winter Escape. An hour from DC beltway & world away. Recharge & relax to the sound of waves & sailboats. Spacious & fully renovated, with modern features, ample outdoor terraces. Enjoy long walks, nature spotting (bald eagles, rays, dolphins), shark tooth collecting. Kayaks provided! Short drive to Solomons Island, and local amenities: restaurants, bars, store, national parks & vineyards. No parties or events. Only relaxing.
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Waterfront 4-BR home w/ hot tub & charging station
Immaculately maintained 4-bedroom waterfront home + home gym on Cobb Island with water views from every window! Four beach cruiser bikes & private dock w/ 4 kayaks, to enjoy the peaceful Neale Sound. Hot tub + private deck off of the kitchen. Wall of windows inside the home, flooded w/ natural sunlight. Views of the sound & the river side of the island. 3 BR are large (2 King beds/1 Queen), w/ their own BA (1 BR w/ BA is on 1st floor, no stairs). Smart TV's in 3 BR's. Great entertaining space!
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The River House, a Wicomico Beach Retreat
Located right on the water of the Wicomico River with a private sandy beach, The River House will become your favorite retreat! This 5 bdrm, 3 bath fully stocked home has all the convenience of modern construction (including wifi) but maintains the vintage charm of the original property. The acre+ plot is very private with spectacular forest & water views. Fun can be found in every direction and for all ages! It has two bottom floor bed/bath combos, plus a fabulous sleeping loft for the kids!
FamilyIndoor spacesCleanliness

Soul Oasis - home on the Chesapeake Bay
Listen to the waves of the Chesapeake Bay from the trex deck. There are 2 private community beaches in the neighborhood where you can find fossils and sharks teeth. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer around the house! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.
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Designer owned Coastal getaway retreat
Enjoy our private, above-garage hideaway apartment with private beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home. You have a private entrance. Come and go as you please! Note: We are a peanut-free and smoke free property. RELAX in our chic, private loft just minutes from Chesapeake beaches and 10 minutes from Solomons Island & Calvert Cliffs. You will have private access to our amazing beach just a 5 minute drive away. Please let us know if you plan to use it!
KitchenIndoor spacesTV

Historic Apothecary | 2 Master Suites | Old Town
Majestic, pre-Civil War Italianate brick home in favored southeast Old Town. Steps away from King Street and 2 blocks to the waterfront, location is unbeatable! This 3-story home established in the 1800s served as a former apothecary. New renovations offer utmost luxury, distinctive architecture with genuine hospitality and true sense of history and charm. 2 Masters Suites 4K 65in TVs w/ Streaming Hi-Speed Internet Dedicated Workspace 24 hr Self Check-in Washer/Dryer Free parking upon request
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*Scenic Waterfront Hideaway*
YOUR WATERFRONT OASIS AWAITS! If you are looking for a true getaway, look no further. Tucked away on a small, peaceful island, this hidden gem is uniquely surrounded by 3 bodies of water: The Potomac River, the Wicomico River, and Neale Sound. This quiet island oasis offers the perfect place to step away from the busy world! This cottage is incredibly special to us. For four generations, it has been a sanctuary for our family-filled with love, laughter, and countless memories.
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Waterfront home, private dock
Relax right next to the water in this tranquil Montross getaway. Fish, crab, kayak, paddleboard, or just sit on the swing and watch dolphins, eagles, herons, and stingrays from your private dock. Dine outdoors on the spacious deck, spend some some quality family time with an in-ground trampoline, tree swing, cornhole, bocce ball, spikeball, and a unique custom-built treehouse. Or just stay inside, relax, and enjoy the views, with an indoor electric fireplace and jacuzzi bathtub.
FamilyKitchenComfort

Little House by the water
Serenity - Privacy - Beauty - This little house by the water has it all. New Sealy queen size mattress, well equipped kitchen, Cuisinart coffee maker, full oven, glass topped stove, new refrigerator, and fully screened porch with water view. Perfect for 1 or 2 adults looking to get off the grid and recharge. In St. Mary's County,MD, just 90 minutes south of Washington DC. However, the space is small and it is really a studio apartment as I think the pictures make evident.
KitchenIndoor spacesBathroom

Waterfront, 3 Beaches, Dock + Kayaks, Potomac
Relax - Star Gaze - Kayaks/Paddleboard - Hike - Fish - Swim - Beach & more! ☀️ Waterfront w/Dock 👨🍳 Gas griddle 🛶 Kayaks/Paddleboard 🔥 Fire pit ⛱️ 3 Community Beaches 🎯 Gameroom 🐶 Dogs OK (Max 2) ⚡️EV Outlet The Riverside Retreat in Montross, VA is the perfect spot to relax and connect with nature. We offer a peaceful sanctuary that families & small groups love to visit! Book your getaway today or ❤️ us for next time!
KitchenIndoor spacesHospitality

*Brand New | Modern Farmhouse | Lux 4 BR | Near DC
Relax with the whole family at this peaceful estate. Newly Remodeled Modern Farmhouse. Enjoy a stylish master bedroom with a double shower and deep freestanding soaker tub. Plenty of areas to relax in and watch movies or enjoy the beauty of the 100-foot-tall trees on the spacious 2-acre lot. Have fun with the Queen-sized bunk beds or if you have a little work to do you can use the home office complete with docking station, web cam and double large screen monitors.
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Popular amenities for Southern Maryland family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy Cottage, Hot Tub, BlockToBeach, 1hr to DC
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Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach
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Peace Point - Waterfront, Secluded, Home w/hot tub
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The Lake Oasis Retreat *cozy, serene, relaxing*
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Beach Retreat
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Bayfront Walk-Out Beach Home | Sunrise & Fire Pit
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Potomac River Getaway
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Waterfront Oasis! Hot tub! 2+ acres - Sleeps 8
Indoor spacesFamilyHot tub
Family- and pet-friendly home rentals

Essex Mill Pond
KitchenIndoor spacesTV

Riverfront Home w/Dock · Fire Pit · Kids Play Area
FamilyIndoor spacesLong stay

Beautiful Rural Suite near Washington, D.C.
FamilyIndoor spacesHospitality

The Bird's Nest at Holly Bluff-Riverfront. Beach.
FamilyKitchenCleanliness

Peaceful waterfront home, 1-hour from DC
KitchenFamilyWi-Fi

Rolling Stone Farmhouse 2m Historic St. Marys City
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Old World Cottage/Fabulous Sunsets/Polite Pets OK
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Peaceful Waterfront Retreat on The Bay
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Family-friendly home rentals with a pool

Historic Rousby Hall, Waterfront, Pool, Beach
FamilyIndoor spacesNearby

Cottage on Solitude Creek, Hot Tub, Pool & Firepit
Indoor spacesFamilyCheck-in

The Loft at Sailor's Retreat. Waterfront Apartment
KitchenIndoor spacesHeating

The Little Gypsy BoHome
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Coastal Waterfront Escape + Hot Tub & Kayaks
FamilyKitchenEV charging

Luxury Farmette -Private & Secluded-1hr to DC
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Cozy Private Entry 1BR1BA Suite Close to GMU & DC
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Serenity Bay-PrivPool-HotTub-AskAbout2NightStays!
FamilyIndoor spacesBarbecue
Destinations to explore
- New York City Holiday rentals
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- Washington Holiday rentals
- Ocean City Holiday rentals
- Pittsburgh Holiday rentals
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- Raleigh Holiday rentals
- Wilmington Holiday rentals
- Jersey City Holiday rentals
- Baltimore Holiday rentals
- Newark Holiday rentals
- Richmond Holiday rentals
- House rentals Southern Maryland
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- Hotel rooms Southern Maryland
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- Rentals with a hot tub Southern Maryland
- Bed and breakfasts Southern Maryland
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- Pet-friendly rentals Southern Maryland
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- Cottage rentals Southern Maryland
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- Rentals with a kayak Southern Maryland
- Rentals with beach access Southern Maryland
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- Waterfront rentals Southern Maryland
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- Family-friendly rentals Maryland
- Family-friendly rentals United States
- Georgetown University
- National Mall
- The White House
- Walter E Washington Convention Center
- Nationals Park
- FedExField
- Arlington National Cemetery
- National Museum of African American History and Culture
- Capital One Arena
- The Anthem
- Washington Monument
- Georgetown Waterfront Park
- Howard University
- Smithsonian National Zoological Park
- National Harbor
- Museum of the Bible
- Smithsonian National Air and Space Museum
- Smithsonian American Art Museum
- Tysons Corner Center
- The Pentagon
- Great Falls Park
- Catholic University Of America
- George Mason University
- Breezy Point Beach & Campground





