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Family-friendly vacation 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 favorite
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 --

Indoor spacesFamilyValue

4.92 out of 5 average rating, 267 reviews
Top guest favorite
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, 140 reviews
Top guest favorite
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!

FamilyKitchenWalkability

4.91 out of 5 average rating, 128 reviews
Top guest favorite
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.

FamilyKitchenHiking

4.97 out of 5 average rating, 113 reviews
Top guest favorite
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.

KitchenFamilyAccess

4.96 out of 5 average rating, 274 reviews
Top guest favorite
Home in Cobb Island

*Solitude At Sunset*

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.

KitchenFamilyOutdoor spaces

4.97 out of 5 average rating, 102 reviews
Top guest favorite
Home in Montross

Waterfront, 3 Beaches, Dock + Kayaks, Potomac

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!

Indoor spacesFamilyAccess

4.98 out of 5 average rating, 158 reviews
Top guest favorite
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.

Indoor spacesFamilyOutdoor spaces

4.97 out of 5 average rating, 108 reviews
Top guest favorite
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. However, the space is small and it is really a studio apartment as I think the pictures make evident.

FamilyIndoor spacesCleanliness

4.94 out of 5 average rating, 186 reviews
Top guest favorite
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

Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

KitchenFamilySleep quality

4.99 out of 5 average rating, 142 reviews
Top guest favorite
A spacious open-concept living area features large windows offering unobstructed views of the water and sunset. A comfortable sectional sofa is positioned near the windows, with a dining table visible in the background. Natural light fills the space, enhancing the tranquil setting.
Home in Leonardtown

Water's Edge Cottage | Luxury Retreat

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”).

KitchenFamilyQuiet

4.99 out of 5 average rating, 139 reviews
Top guest favorite
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).

FamilyKitchenRiver

4.99 out of 5 average rating, 175 reviews

Popular amenities for Southern Maryland family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favorite
Home in Colonial Beach

River Refresh - Waterfront with Spa on Placid Bay

KitchenFamilyComfort

4.96 out of 5 average rating, 135 reviews
Top guest favorite
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

KitchenIndoor spacesValue

4.97 out of 5 average rating, 105 reviews
Top guest favorite
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.

FamilyKitchenCleanliness

5.0 out of 5 average rating, 105 reviews
Guest favorite
Home in Lexington Park

Serenity Bay-PrivPool-HotTub-AskAbout2NightStays!

KitchenFamilyBackyard

4.93 out of 5 average rating, 104 reviews
Guest favorite
An aerial view captures a spacious property bordered by water on two sides. A sandy beach area extends along the shoreline, surrounded by trees. The house features a large deck facing the water, and the landscape showcases a mix of greenery and open space.
Home in Heathsville

Private Beach Oasis, Arcade & Theater

KitchenFamilyGetting around

4.9 out of 5 average rating, 105 reviews
Top guest favorite
Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Indoor spacesFamilyNearby

5.0 out of 5 average rating, 214 reviews
Top guest favorite
Apartment in Upper Marlboro

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

Indoor spacesFamilyPets

4.94 out of 5 average rating, 215 reviews
Guest favorite
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 spacesBeach

4.86 out of 5 average rating, 103 reviews

Family- and pet-friendly home rentals

Guest favorite
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

Indoor spacesKitchenAccuracy

4.91 out of 5 average rating, 101 reviews
Guest favorite
Farm stay in Heathsville

Fleets Cove Farm *PETS STAY FREE*

FamilyIndoor spacesAir conditioning

4.98 out of 5 average rating, 122 reviews
Top guest favorite
The exterior of a single-story beach house is visible, featuring white siding and landscaped areas. A stone pathway leads to a cozy outdoor seating area with light cushions. Lush greenery and mature trees are present, contributing to a serene atmosphere.
Home in Lusby

Cove Point Cottage with Chesapeake Bay views

Indoor spacesFamilyHospitality

4.98 out of 5 average rating, 257 reviews
Top guest favorite
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.

KitchenIndoor spacesRiver

4.9 out of 5 average rating, 311 reviews
Top guest favorite
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

Indoor spacesFamilyBiking

4.95 out of 5 average rating, 107 reviews
Guest favorite
A charming 1930's farmhouse is framed by lush greenery and a spacious lawn. The exterior is enhanced by a welcoming front porch and surrounded by mature trees, providing a serene rural setting. A gravel path leads to the house, indicating easy access.
Home in Park Hall

Rolling Stone Farmhouse 2m Historic St. Marys City

FamilyIndoor spacesCheck-in

4.93 out of 5 average rating, 134 reviews
Guest favorite
An aerial view showcases the expansive property bordered by a winding river, surrounded by vibrant foliage in autumn colors. Open fields and mature trees are visible, providing a sense of spaciousness and privacy. The tranquil water reflects the seasonal hues, enhancing the serene landscape.
Home in Montross

Potomac Waterfront Home and Estate

Indoor spacesKitchenNearby

4.86 out of 5 average rating, 145 reviews
Top guest favorite
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

FamilyKitchenGetting around

4.98 out of 5 average rating, 138 reviews

Family-friendly home rentals with a pool

Top guest favorite
Farm stay in Huntingtown

Luxury Farmette -Private & Secluded-1hr to DC

FamilyIndoor spacesGetting around

5.0 out of 5 average rating, 125 reviews
Top guest favorite
A cozy living area features a spacious sectional couch adorned with patterned cushions. A wooden coffee table sits centrally, with a decorative rug beneath. A brick fireplace is present, flanked by windows allowing natural light, and a green door leads to the exterior.
Guesthouse in Cambridge

Rosses Chance Guest House

FamilyIndoor spacesLaundry

4.99 out of 5 average rating, 144 reviews
Superhost
Home in Waldorf

*Brand New | Modern Farmhouse | Lux 4 BR | Near DC

FamilyIndoor spacesAmenities

4.83 out of 5 average rating, 119 reviews
Top guest favorite
An aerial view captures a spacious home set on a wooded parcel adjacent to a serene body of water. The exterior features a large swimming pool surrounded by decking, with a manicured lawn and tall trees creating a natural boundary.
Home in Cambridge

Gorgeous, Waterfront Home Is Perfect for Families!

Indoor spacesKitchenQuiet

4.96 out of 5 average rating, 140 reviews
Superhost
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

FamilyIndoor spacesWalkability

4.92 out of 5 average rating, 232 reviews
Top guest favorite
A red barn-style building is positioned on a lush green lawn, surrounded by trees and residential structures. A porch is visible on the upper level, and a colorful wheel mural decorates the front. A gravel path leads to the entrance.
Guesthouse in Cambridge

The Loft at Sailor's Retreat. Waterfront Apartment

KitchenIndoor spacesCondition

4.99 out of 5 average rating, 119 reviews
Top guest favorite
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

KitchenFamilyAccess

4.99 out of 5 average rating, 251 reviews
Guest favorite
An aerial view captures the expansive property, featuring a large home surrounded by lush green lawns and mature trees. A heated in-ground pool is visible in the backyard, adjacent to a serene water body, with an expansive landscape enhancing the tranquil setting.
Cabin in St. Michaels

True St. Michaels 6 Acre Waterfront w/heated pool

Indoor spacesFamilyLayout

4.99 out of 5 average rating, 124 reviews

Destinations to explore