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Family-friendly holiday rentals in Southern Maryland

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Top-rated family-friendly rentals in Southern Maryland

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
The vintage A-frame home is nestled amongst trees, featuring a deck with a canopy in the foreground. A stone path leads to the entrance, where large windows allow for ample natural light. The surrounding landscape is adorned with greenery and decorative plants.
Cabin in Lusby

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 --

KitchenIndoor spacesGetting around

4.91 out of 5 average rating, 269 reviews
Top Guest favourite
An aerial view captures the waterfront home surrounded by lush greenery with a private dock visible by the water. The neatly maintained property features landscaped lawns and nearby homes, illustrating a serene setting alongside Neale Sound.
Home in Cobb Island

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!

FamilyKitchenAmenities

4.99 out of 5 average rating, 142 reviews
Top Guest favourite
A wooden dock extends into calm waters, showcasing a boat moored at the end. The serene surface reflects the pastel colors of the sky during dusk. Wooden posts line the edges of the dock, enhancing the tranquil setting.
Home in Newburg

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!

FamilyKitchenAccuracy

4.91 out of 5 average rating, 129 reviews
Top Guest favourite
Four black Adirondack chairs are arranged on a lush green lawn, facing the calm waters of Chesapeake Bay. Gentle waves reflect the bright blue sky, offering a serene view. Small bushes line the edge of the property, providing a natural border.
Home in Lusby

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.

Indoor spacesFamilyComfort

4.97 out of 5 average rating, 114 reviews
Top Guest favourite
Cottage in Leonardtown

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

KitchenFamilyWi-Fi

4.96 out of 5 average rating, 277 reviews
Top Guest favourite
A bright and open living space features large windows that provide views of the river. A long dining table is accompanied by upholstered chairs. A modern kitchen counter with stools is visible, along with a chandelier overhead and a cozy fireplace on one side.
Home in St. Leonard

Blue Pearl-Luxury estate with private dock/jacuzzi

The Blue Pearl is a luxurious river front estate with a private pier to catch crabs, fish and kayak. Soak in the outdoor jacuzzi and enjoy the river life. Three bedrooms with three full bath en-suites and over 2800 square feet of luxury accommodations await you. Office has Queen sleeper sofa. Pull up to your private boat dock, catch blue crabs with the provided traps, toast s’mores in the firepit while sitting in your Adirondack chairs. Enjoy two decks to view the sunrises and sunsets.

Indoor spacesFamilyCleanliness

4.97 out of 5 average rating, 107 reviews
Top Guest favourite
Home in Cobb Island

*Where Eagles Soar* Peaceful Waterfront Retreat.

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.

KitchenIndoor spacesTV

4.97 out of 5 average rating, 104 reviews
Guest favourite
Home in Montross

Waterfront, 3 Beaches, Dock+Kayak, Potomac, Dog OK

Relax - Star Gaze - Kayak/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 the Northern Neck of 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!

KitchenFamilyAccuracy

4.98 out of 5 average rating, 161 reviews
Top Guest favourite
A private dock extends into the calm water, featuring a wooden platform and seating areas. A vibrant blue paddleboard rests on the grassy shoreline, while an in-ground trampoline is seen nearby. The scene is framed by trees under a clear blue sky.
Home in Montross

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.

FamilyKitchenBathroom

4.97 out of 5 average rating, 111 reviews
Top Guest favourite
A covered deck area features a large black dining table surrounded by striped chairs. A ceiling fan is present above. Scenic views of the water and shoreline are framed by tall trees, creating a serene outdoor dining space.
Home in Cambridge

Sunset Breezes - quiet waterfront retreat

Enjoy well equipped waterfront home styled after historic lighthouses. Relax in the hammock by the water under the pines; Enjoy smores by the fire pit. Wood included. Free use of 4 kayaks, 2 paddleboards, and a 3 person canoe. Yard games include corn hole, croquet, & bocce. Dine on the deck while enjoying beautiful sunsets. Bring your cameras for local wildlife. NEW Fun & Fitness Barn: sauna, golf simulator, free weights, game space and more. Ask about access code and hours.

KitchenFamilyLayout

4.99 out of 5 average rating, 228 reviews
Top Guest favourite
A view from the property shows a grassy area leading to the water. A screened porch is visible, providing a tranquil space. The river reflects the blue sky and fluffy clouds, with trees lining the opposite bank. A wooden dock extends into the water.
Guesthouse in Bushwood

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. Childlren under the age of 12 and pets are not allowed.

FamilyIndoor spacesSolo travel

4.94 out of 5 average rating, 188 reviews
Top Guest favourite
The historic home features a charming exterior with a mix of white clapboard and dark shingles. An inviting porch is framed by green shutters and surrounded by well-maintained landscaping. A gravel driveway leads to the front entrance, enhancing the property’s welcoming appeal.
Home in Lusby

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).

FamilyKitchenParking

4.99 out of 5 average rating, 179 reviews

Popular amenities for Southern Maryland family-friendly rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top Guest favourite
A serene dock extends over calm waters, surrounded by lush greenery. A small orange kayak is secured nearby. In the background, a custom waterfront home is nestled among tall trees, providing a natural and tranquil setting.
Home in Mechanicsville

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

Indoor spacesFamilyRiver

5.0 out of 5 average rating, 107 reviews
Top Guest favourite
A tranquil beach scene presents soft sand leading to calm water, framed by an open sky dotted with clouds. A weathered log rests on the shoreline, while distant rocky formations add interest to the horizon.
Cottage in St. Leonard

Cozy Cottage, Hot Tub, BlockToBeach, 1hr to DC

FamilyIndoor spacesCheck-in

4.92 out of 5 average rating, 201 reviews
Top Guest favourite
A scenic view of a sunset over the water, with a silhouette of a person kayaking. Adjacent, a cozy seating area is set up around a fire pit, surrounded by trees. In the foreground, a table with wine and glasses is shaded by a red umbrella, beside a hot tub.
Home in Dameron

Peace Point - Waterfront, Secluded, Home w/hot tub

FamilyIndoor spacesCleanliness

4.99 out of 5 average rating, 142 reviews
Guest favourite
Home in Colonial Beach

River Refresh - Waterfront with Spa on Placid Bay

KitchenFamilyBathroom

4.96 out of 5 average rating, 137 reviews
Guest favourite
A window frame is visible, showcasing a scenic view of the Potomac River. A telescope is positioned within the frame, aimed towards the tranquil waters. The horizon features trees and a distant shoreline, while a wooden fence adds a touch of structure to the foreground.
Home in Montross

Potomac River Getaway

FamilyIndoor spacesPets

4.87 out of 5 average rating, 104 reviews
Superhost
A well-maintained dock extends over clear water, providing access to a private beach area lined with sand. The surroundings feature trees and several nearby structures, enhancing the outdoor space. The scene is set beneath a blue sky with scattered clouds.
Home in Hague

Year-Round Heated Indoor Pool & Beach Sleeps 16

KitchenFamilyCheckout

4.92 out of 5 average rating, 106 reviews
Top Guest favourite
Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

KitchenFamilyParks

5.0 out of 5 average rating, 217 reviews
Guest favourite
An aerial view showcases a lush green landscape surrounding a peaceful shoreline. The sandy beach meets calm waters, framed by dense trees. The varied colors of the water create a serene contrast against the vibrant greenery, presenting a tranquil natural setting.
Cottage in Lusby

Hot Tub Hideaway by Shark Tooth Shores

Indoor spacesFamilyCleanliness

4.85 out of 5 average rating, 101 reviews

Family- and pet-friendly home rentals

Top Guest favourite
The charming exterior of a waterfront cottage, featuring a white picket fence and a welcoming front deck. Large windows allow for natural light, while vibrant surroundings enhance the coastal feel. The front porch is partially shaded by lush greenery, inviting relaxation and enjoyment of the outdoors.
Cottage in North Beach

Cozy Waterfront Cottage - Pet Friendly

FamilyKitchenCondition

4.95 out of 5 average rating, 111 reviews
Guest favourite
An aerial view of a waterfront property showcases a red-roofed home bordered by lush green grass. A private pier extends into the calm water, while a play area with a playset sits adjacent to the house, emphasizing the outdoor living space along the Potomac River.
Home in Newburg

Peaceful waterfront home, 1-hour from DC

KitchenIndoor spacesBeach

4.91 out of 5 average rating, 102 reviews
Guest favourite
A wooden staircase illuminated by soft lights leads down to a private dock. Reflections of trees and evening sky are seen on the calm water of St. Leonard Creek. A sailboat is moored at the end of the dock, adding to the serene waterside ambiance.
Cabin in Lusby

Peaceful Waterfront Retreat on The Bay

FamilyKitchenRiver

4.9 out of 5 average rating, 324 reviews
Guest favourite
Home in Montross

Riverfront Home w/Dock · Fire Pit · Kids Play Area

Indoor spacesFamilyCheck-in

4.92 out of 5 average rating, 106 reviews
Top Guest favourite
A spacious wooden deck is showcased, extending from the house and featuring several outdoor chairs arranged around a table. The sun sets in the background, casting a warm glow over the grassy yard and the nearby water, enhancing the serene ambiance.
Home in Leonardtown

The River House: A private waterfront oasis…

Indoor spacesFamilyBiking

4.94 out of 5 average rating, 100 reviews
Top Guest favourite
The image captures a serene waterfront scene, showcasing a long wooden dock extending into the calm river. Lush greenery lines the riverbank, while a clear blue sky with scattered clouds provides a picturesque backdrop. The tranquil water reflects the surrounding landscape.
Apartment in Lexington Park

Historic St. Mary's City, MD

Indoor spacesKitchenTV

4.97 out of 5 average rating, 626 reviews
Top Guest favourite
A cozy sitting area features a comfortable blue sofa adorned with cushions. Large glass doors provide access to the outdoor space, complemented by colorful curtains. A small dining table and chairs are visible outside, framed by a patterned area rug on the wooden floor.
Guest suite in La Plata

Beautiful Rural Suite near Washington, D.C.

FamilyKitchenBackyard

4.9 out of 5 average rating, 314 reviews
Top Guest favourite
A spacious outdoor area is equipped with shaded seating, including a sofa set and a coffee table, arranged on a patterned rug. A hammock hangs in the background, and a fenced yard provides a private setting, surrounded by trees for a tranquil atmosphere.
Home in Colonial Beach

Riverview on the Potomac

Indoor spacesKitchenRiver

4.98 out of 5 average rating, 139 reviews

Family-friendly home rentals with a pool

Top Guest favourite
A bright living area features large windows offering panoramic water views. A wooden dining table accommodates six, while a comfortable seating arrangement includes a blue armchair and a neutral-toned sofa. A ceiling fan is visible above, and decorative coastal artwork adorns the walls.
Apartment in Colonial Beach

Sail Away To - Beachfront Views & Private Balcony

Indoor spacesKitchenLocation

4.94 out of 5 average rating, 101 reviews
Top Guest favourite
Farm stay in Huntingtown

Luxury Farmette -Private & Secluded-1hr to DC

FamilyIndoor spacesBiking

4.99 out of 5 average rating, 129 reviews
Guest favourite
An aerial view of the house showcases a spacious deck with comfortable seating, surrounded by a railing. A dock extends into the water, equipped with a covered boat lift. Lush greenery borders the property, providing a serene backdrop.
Home in Montross

Coastal Waterfront Escape Fire Pit, Dock & Kayaks

Indoor spacesFamilyHot tub

4.96 out of 5 average rating, 107 reviews
Guest favourite
A private beach area is depicted with soft, sandy ground, featuring two beach chairs under a blue umbrella. Calm waters extend to the horizon, complemented by a wooden dock and a distant view of the opposite shore under a clear, blue sky.
Home in Montross

The Glebe

Indoor spacesKitchenBathroom

4.92 out of 5 average rating, 234 reviews
Top Guest favourite
A spacious living area features two comfortable sofas, one draped with a soft blanket. Natural light streams through large windows, highlighting the wooden flooring. A small wooden table is visible in the background, and a decorative piece hangs above the mantel.
Home in Tracys Landing

The Little Gypsy BoHome

KitchenIndoor spacesOutdoor spaces

4.99 out of 5 average rating, 255 reviews
Superhost
Home in Waldorf

Private Pool | Modern | Lux 4 BR Retreat | Near DC

FamilyIndoor spacesCheckout

4.84 out of 5 average rating, 123 reviews
Guest favourite
Apartment in Upper Marlboro

Kone Oasis- hot tub, pool, theater/game rm.

KitchenFamilyBeach

4.94 out of 5 average rating, 218 reviews
Top Guest favourite
A modern guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.
Cottage in St. Michaels

La Casita on Harris Creek, St. Michaels

KitchenFamilyBathroom

4.98 out of 5 average rating, 204 reviews

Destinations to explore