Family-friendly vacation rentals in Chincoteague

The vintage cottage features a charming façade with light blue siding and a gabled roof. A welcoming entryway is framed by shrubs and decorative pumpkins, while large windows invite natural light. Steps lead to a front porch with a cozy seating area.

4.94 out of 5 average rating, 188 reviews

Maggie’s Cottage on Poplar - Our Happy Place!

Step back in time and enjoy the simplicity of this 2 bedroom, 1 bath vintage Chincoteague cottage located in the heart of town. Quaint, quiet and cozy - Maggie’s Cottage is the perfect retreat to slow down, relax, and enjoy an island get away... anytime of the year! Maggie’s Cottage is just right for a couples get away, girls trip, a solo retreat, or a small family vacation. Well stocked and comfortable- you will feel right at home. Walking distance to local dining, shopping and waterfront!🐴🦪🌅

Guest suite in Chincoteague

A cozy bedroom features a white, wooden bed frame with a floral-patterned coverlet. Two pillows and a decorative cushion rest against the headboard. A bedside table holds a lamp, and natural light enters through a window with soft curtains.

4.94 out of 5 average rating, 335 reviews

Baywatch North-Waterfront & Roaming Ponies

Calender open for super deals on weekly Summer rentals 2026. Lovely space! 2 queen bdrm unit decorated with coastal charm, each with a door to the outside. Make-shift kitchen with microwave, small fridge, stoked Keuring coffee and tea bar, shared patio cooking area, bbq grill, fantastic view, beach items, plenty of parking, very quiet, out of the way of everything, super laid back host living in the other portion of the house. There is no living room. Labradors and cats on premises, ponies too!

4.94 out of 5 average rating, 129 reviews

Dragonfli Bay House on Chincoteague Island

Relax in this calm, stylish space. This home has been lovingly refreshed by its current owners. Every detail has been considered. Inside you will find well appointed rooms designed for function and comfort. Outside, tranquility awaits you. Enjoy morning coffee overlooking the water, kayaking on the bay, end the day relaxing by the fire. Head to Assateague to swim, surf fish or hike to the famed lighthouse. Return with the day's catch to utilize the fish cleaning station and outdoor shower.

4.94 out of 5 average rating, 510 reviews

A quaint tiny house presents a welcoming exterior with a red facade and inviting black door. Comfortable seating is arranged on green grass under a large white umbrella, surrounded by planters with flowers. Lush greenery and a pathway enhance the serene outdoor setting.

Tiny home in Accomac

Little Red House on a Farm - Quiet Rural Waterview

The Little Red House VA is a cozy tiny home on a 50-acre farm, surrounded by fields, woods, marsh, and a creek. Curated with hygge comfort and efficiency, you'll love the natural light and calm decor. • Escape the noise & reset in nature • Peaceful sleeping • Thoughtful interior design • Large full bath • Comfy patio for coffee, cocktails, and epic stargazing • Firepit with wood provided • Large private outdoor shower surrounded by woods • Wide open spaces • Fast WIFI • Superhost for 10+ years

A light-filled living room is presented with soft beige seating arranged around a round, patterned coffee table. A landscape artwork adorns the wall above the couch. Natural light streams through a nearby window, highlighting a plant tucked in the corner.

4.93 out of 5 average rating, 176 reviews

Adorable Beach Cottage Just Steps From Town & Bay

New to AirBNB! Welcome to Wiggle Bay, a darling 1955 2 BR cottage nestled in the heart of "one of the most beautiful, charming small towns in Virginia." -Enjoy a bay breeze on the screened front porch--heaven! --Stroll to local bookshop, coffee house, theatre, or Chincoteague Waterfront Park to feed the ducks--all just steps from your front door! -Situated on a quiet residential street -Just 4 blocks to Maddox Blvd (where all the action is) -2.3 mi to Assateague Seashore/Chincoteague Refuge

4.99 out of 5 average rating, 295 reviews

A wooden deck is shown overlooking a serene pond, framed by lush trees. A dining table with chairs is set for outdoor enjoyment, while soft natural light reflects off the water's surface, creating a peaceful ambiance.

Farm stay in Onancock

Private romantic pet friendly waterfront cottage

On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

A charming two-story island home is nestled among tall trees, providing a natural setting. The structure features a sloped roof and a front porch with a railing. Sunlight filters through the branches, casting dappled shadows on the ground.

4.97 out of 5 average rating, 181 reviews

Charming Island Home "Sandy Pines"

Come and enjoy a nice, relaxing vacation at this charming island home. "Sandy Pines" lies just a half a block from the water and a block and a half from the bridge to Assateague (where the beach is). The downstairs features a living room and dining room, 2 bedrooms (equipped with two twin beds each), a lovely kitchen, full bathroom and screened porch. On the second level you'll find the master bedroom with a private full bathroom, movie/game/yoga room, and a 2nd fully screened porch.

A serene waterfront view captures a calm body of water reflecting a colorful sunset. Silhouettes of grass line the shore, while a long pier extends into the distance, adding depth to the tranquil scene.

4.95 out of 5 average rating, 177 reviews

Summer's Sea Shanty on Chincoteague Island

Summer's Sea Shanty is a delightful Chincoteague coastal cottage that’s perfect for couples, families, or small groups of friends. We've worked hard to make this the ideal modern day beach retreat. This home boasts screened in front and back porches, a fire pit, an open/functional floor plan. We're pet and kid friendly with luxury linens and rugs and dish ware... We're proud to be the best of the best on the island. We're centrally located and minutes from Assateague National Seashore.

4.98 out of 5 average rating, 112 reviews

A modern barn-style exterior is shown with a soft twilight glow. Inside, a cozy loft bedroom features a spacious bed adorned with decorative pillows. A bright dining area is visible, highlighting wooden accents and seating. Two playful goats are seen exploring their cozy enclosure.

Loft in Pocomoke City

Cozy Barn Loft: Country Views & Central to Beaches

Relax and recharge as you soak in the country views while enjoying this cozy space. A private entrance leads upstairs to the loft, located above our renovated barn. Enjoy your days at the beach, boating, fishing, birding, and more. Return home to be greeted by goats as you pull in the drive. Coffee, tea, and farm fresh eggs will be waiting for your arrival. Centrally located between the beaches of Chincoteague, Va and Ocean City, MD. Beach gear provided as well.

4.87 out of 5 average rating, 157 reviews

A spacious houseboat is docked securely along the water's edge, featuring large windows and a deck area. The surroundings include trees and a sandy space, creating a coastal atmosphere. The sky displays soft clouds illuminated by the setting sun.

Houseboat in Snow Hill

"Jolly"- Houseboat Getaway

#BoatLife! Jolly is a 42ft Holiday Mansion. Baywater Landing offers a laid back, coastal style. It buzzes with watermen & boaters by day & is a peaceful stargazing hotspot by night. She features a master suite & 3 outside deck areas to enjoy! Just 35 minutes from Ocean City, Assateague Island, and Chincoteague Island, this is the epicenter of everything coastal! A firepit in the sand just outside your door round out everything you'll need for a stress-free vacation.

4.77 out of 5 average rating, 239 reviews

The exterior of a two-story house is shown, featuring a light-colored façade and multiple windows. A staircase leads to an entrance at the front. A well-maintained lawn surrounds the structure, and a friendly corgi is visible on the grass.

Guest suite in Crisfield

The Serenity House

Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with SmartTV, equipped kitchenette, work space with WiFi, mudroom and laundry on the first floor. Large yard with big mature shade trees nestled in a quiet neighborhood. One corgi and two cats live on the property. The pets are not allowed into the guest rooms. Continental breakfast served in the shared space. Private entrance, off street parking available.

4.97 out of 5 average rating, 621 reviews

The charming carriage house features a light-colored exterior with white trim and a metal roof. Two garage doors and multiple windows offer ample natural light, while a gravel driveway provides access to the entrance. Surrounding trees add a touch of greenery to the serene setting.

Guest suite in Berlin

Ayers Creek Carriage House

Our beautiful carriage house is located on 5 pristine acres along, scenic Ayers Creek, offering year round beauty. Only minutes from Assateague Island, Berlin, and Ocean City. Serene with abundant wildlife. Ideal oasis for outdoor enthusiasts. Worcester County Maryland Rental License #1324

Popular amenities for Chincoteague family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a pool

Superhost

The image captures the exterior of a charming blue house surrounded by vibrant flower beds, primarily featuring red blooms. A yellow sign displaying the house name and address stands prominently in the foreground. Soft evening light enhances the welcoming atmosphere.

Bungalow in Horntown

4.8 out of 5 average rating, 158 reviews

Nature's retreat @ the Bug-a-Boo. Beaches nearby

4.98 out of 5 average rating, 260 reviews

A modern living area features a spacious gray sofa and a wooden coffee table, complemented by a cozy area rug. Large glass doors open to a private oceanfront balcony, allowing natural light to fill the space. Decorative accents include a wall-mounted surfboard and a round mirror.

Apartment in Ocean City

OceanFront-Fireplace-sleeps4-Balcony-King-Disney+

4.93 out of 5 average rating, 105 reviews

The cottage is presented in a well-maintained landscape, featuring a light-colored exterior with dark shutters and a welcoming front door. Two benches sit on either side of the entrance, with potted plants nearby and a lush green lawn extending into a wooded area behind.

Farm stay in Pittsville

Kits Cottage on "Just Ducky Acres"

Superhost

A vintage pull-behind camper sits by the water's edge, featuring a striking teal color that contrasts with the clear blue sky. Grassy surroundings provide a natural setting, inviting views of the serene shoreline and distant water.

Camper/RV in White Stone

4.88 out of 5 average rating, 136 reviews

“Old Smokey”A cozy, single bedroom, unique getaway

4.97 out of 5 average rating, 191 reviews

A serene waterfront scene is captured at sunset, with vibrant colors reflected in the calm water. A charming building with large windows is illuminated, surrounded by lush trees, and boats are docked along the waterfront, creating a peaceful atmosphere.

Condo in Ocean Pines

Ocean Pines Retreat

Farm stay in Princess Anne

A bright living area features wooden beams and large windows adorned with plaid curtains. A variety of cushions decorate a sectional sofa and a leather couch. A television offers a view of a sports event, while an area rug adds pattern to the wooden floor.

4.95 out of 5 average rating, 112 reviews

Farmhouse located on a horse farm

4.91 out of 5 average rating, 101 reviews

A serene canal view captures waterfront homes reflecting in calm waters at sunset. Docked boats and lush trees frame the scene, showcasing the tranquil atmosphere of the eastern shore. The clear sky hints at the day's end, lending a peaceful ambiance to the surroundings.

Home in Greenbackville

Stunning waterfront panoramic view getaway house

4.89 out of 5 average rating, 157 reviews

An open-plan kitchen and living area feature a light wooden counter with three stools. A fully equipped kitchen is visible, including a refrigerator, while a comfortable seating area with a cream-colored armchair and a coffee table is also present. Natural light enhances the inviting space.

Condo in Ocean City

Water Front Condo w/Pool Short Walk to Beach

Family-friendly home rentals with air conditioning

A cozy bedroom features a spacious bed with striped bedding and decorative pillows. A wooden dresser and nightstand are positioned beside the bed. Natural light enters through a window, complemented by light curtains, while gray curtains frame the room.

4.81 out of 5 average rating, 37 reviews

Holiday Cottages- The Jellyfish Cottage

4.99 out of 5 average rating, 70 reviews

A charming tiny cottage is framed by lush greenery, featuring a welcoming red door and hanging flower baskets. A wooden pathway leads to the entrance, surrounded by a well-maintained lawn and gravel area. The fenced yard enhances the sense of privacy and tranquility.

Tiny home in Parsonsburg

Cozy Cottage Hideaway

Superhost

A sleek building is situated by the water's edge, reflecting the soft hues of a sunset. Clouds scatter across the sky, casting gentle shadows, while pilings extend from the shore into the tranquil bay. The serene scene invites relaxation and appreciation of the natural beauty.

Condo in Chincoteague

4.67 out of 5 average rating, 295 reviews

Le Petit Paradis-Waterfront, pet-friendly Studio

4.83 out of 5 average rating, 274 reviews

A charming beach cottage is displayed in an A-frame design, featuring a large front porch with white railings. Windows are covered by striped awnings, allowing natural light to filter in. The landscaped yard includes low shrubbery, adding to the inviting exterior.

Cottage in Bethany Beach

A-mazing Beach Cottage on Canal & Trolley Route

The exterior of a charming white cottage is showcased, featuring two sets of stairs leading to the front porch. The well-maintained lawn is punctuated by a small garden area, and a decorative figure can be seen near the entrance.

4.97 out of 5 average rating, 39 reviews

Waterfowl Watch Chincoteague Enjoy Christmas here!

A charming two-story building is presented in a row of identical homes, featuring light gray siding and white accents. Each unit has a front door, with some balconies visible above. Lush green grass is maintained in the front yard, framed by colorful landscaping.

4.99 out of 5 average rating, 93 reviews

Steps 2 Beach Rd- Walk 2 Dining- Updated Kitchen!

A coastal retreat is presented in a light-colored two-story home elevated on stilts. A set of steps leads to a covered porch with a railing. A small seating area with yellow chairs is visible beneath the porch. Lush green trees surround the property.

4.99 out of 5 average rating, 69 reviews

Pearl in the Pines

The exterior of Ivy's Cottage showcases a charming gray shingle facade with a welcoming purple front door. A set of steps leads to a spacious porch, which is accompanied by white railings and decorative plants, enhancing the inviting entryway.

4.85 out of 5 average rating, 111 reviews

"3 Sisters" Ivy's Cottage-Lovely downtown cottage

Family-friendly home rentals with Wifi

4.96 out of 5 average rating, 48 reviews

Two charming blue cottages are set against a backdrop of a vibrant rainbow arching across a pastel sky. Each cottage features a welcoming front porch, surrounded by a gravel pathway and a well-maintained garden, creating a serene outdoor atmosphere.

Cabin in Chincoteague

The Nor’easter | Coastal Cabin-Water View + Sunset

Home in Deal Island Historic District

The two-story farmhouse is surrounded by a spacious yard, highlighted by a prominent American flag flying in front. Large windows allow natural light, while the earthy green exterior blends with the surrounding trees. A charming white bench adds to the inviting outdoor space.

4.95 out of 5 average rating, 39 reviews

Rusty Anchor

Four light blue adirondack chairs are arranged beneath a tree adorned with string lights, creating a cozy seating area. A large, detached garage with a light-colored exterior is visible in the background, complemented by a grassy lawn illuminated by soft evening light.

4.98 out of 5 average rating, 88 reviews

Bikes-Kayaks-Outdoor Shower Grill-Firepit-Beach Eq

An aerial view of a two-story duplex is presented, showcasing a well-maintained exterior with white siding and a sloped roof. The spacious lawn is bordered by a white picket fence, and a small shed is visible to the side. A black vehicle is parked nearby, surrounded by lush greenery.

4.88 out of 5 average rating, 24 reviews

Coastal Charm Duplex with Views of Horse Farm

4.93 out of 5 average rating, 71 reviews

A gravel driveway leads towards a rustic boathouse with weathered wooden siding, framed by tall grasses and marshland. The iconic Chincoteague lighthouse can be seen in the distance, completing the scenic view under a clear sky.

Cabin in Chincoteague

The Boathouse: Charming & Historic Waterfront Stay

4.97 out of 5 average rating, 30 reviews

A wooden deck is shown with a round table and four black mesh chairs, facing the calm waters of the Wicomico River. Lush greenery surrounds the area, with a dock visible in the background. The sky features soft clouds, enhancing the serene atmosphere.

Cottage in Princess Anne

Waterfront Cottage in Mt. Vernon

A two-story house is depicted, featuring a light exterior and a gabled roof. A set of stairs leads to a spacious porch with railings. The surrounding area includes a gravel driveway and a fenced yard with patches of greenery.

4.95 out of 5 average rating, 42 reviews

Island Blessing